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1
Karahan, Dag Fulya. "Synthesis Of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1h-pyrazoles By Electrophilic Cyclization." Master's thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12613443/index.pdf.
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Pyrazoles have been intensely studied in the design and synthesis of biologically active agents because they display considerable medicinal activities. Recent studies have shown that integration of a ferrocenyl unit with structural features of pyrazoles can result in the formation of the new products with enhanced or/and unexpected biological activity since several ferrocene derivatives have already been illustrated to be active against a number of tumors. Therefore, we have investigated the electrophilic cyclizations of the hydrazones to afford 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-substituted pyrazole derivatives. First, the requisite hydrazone derivatives were synthesized by the reactions of ferrocenyl propargyl aldehydes or ketones with a series of hydrazines. Then electrophilic cyclizations of these hydrazones were investigated by treating with 4-(nitrophenyl)sulfenyl chloride as electrophile. By employing these electrophilic cyclizations, a series of 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-1H-pyrazoles, 5-ferrocenyl-4-((4-nitrophenyl) sulfenyl)-3-methyl-1H-pyrazoles and 5-ferrocenyl-4-((4-nitrophenyl)sulfenyl)-3-phenyl-1H-pyrazoles have been synthesized in moderate to good yields.
2
Demirci, Deniz. "Synthesis Of 4-phenylselenyl-1h-pyrazoles By Electrophilic Cyclization." Master's thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12613910/index.pdf.
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In this study, the synthesis of 5-ferrocenyl/aryl-4-(phenylselenyl)-1H-pyrazole derivatives was investigated since the integration of ferrocenyl and selenium moieties into pyrazole derivatives may increase their current biological activities. Initially, the starting propargyl aldehydes were synthesized from corresponding acetylenes. Subsequently, propargyl aldehydes were reacted with hydrazines to yield corresponding hydrazones. Then the in situ synthesized hydrazones were subjected to electrophilic cyclization with phenylselenyl chloride, which afforded 5-ferrocenyl/aryl-4-(phenylselenyl)-1H-pyrazoles in one-pot manner. Subsequently, reaction conditions were optimized in terms of electrophile, base, temperature and solvent. Best results were obtained with phenylselenyl chloride and NaHCO3 at room temperature in DCM for ferrocenyl substituted pyrazoles and DCE for aryl substituted pyrazoles. In summary, by employing the electrophilic cyclizations of in situ synthesized acetylenic hydrazones, a variety of 5-ferrocenyl/aryl-4-(phenylselenyl)-1H-pyrazole derivatives were synthesized in one-pot way in moderate to good yields.
3
Barus, M. M. "А new approach to the preparation of 4-difluoromethyl-1Н-pyrazole-3-carboxylic acids." Thesis, БДМУ, 2022. http://dspace.bsmu.edu.ua:8080/xmlui/handle/123456789/19532.
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Yazici, Ceyda. "Synthesis Of 4-iodopyrazole Derivatives." Master's thesis, METU, 2008. http://etd.lib.metu.edu.tr/upload/3/12609750/index.pdf.
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Pyrazoles have been studied for over a century as an important class of
heterocyclic compounds and continue to attract considerable interest due to the
broad range of biological activities they possess. The electrophilic cyclization of
the acetylenic hydrazones initiated by molecular iodine could provide new ways of
synthesizing biologically active 4-iodopyrazole derivatives, which are important
precursors for the synthesis of highly substituted pyrazole derivatives. For this
reason, we investigated the synthesis of 4-iodopyrazole derivatives, such as 1-aryl-
5-alkyl/aryl-4-iodopyrazoles, starting from phenylhydrazine and ,-acetylenic
aldehyde derivatives. Initially, ,-acetylenic aldehydes were synthesized by
formylation reaction of corresponding alkynes with DMF. Then, hydrazone
derivatives of these aldehydes were prepared by heating them with
phenylhydrazine in a neat manner at 55 °C for 5 h. Finally, acetylenic phenyl hydrazone derivatives were subjected to electrophilic cyclization by treating with excess molecular iodine at 80 °
C for 3 h. Although electrophilic cyclization is commonly used in organic chemistry, it has not been employed for the cyclization of acetylenic phenyl hydrazones to pyrazole derivatives. Under optimized conditions, these reactions afforded 1-aryl-5-alkyl/aryl-4-iodopyrazole derivatives in moderate to good yields as the single or the major product of the reactions. In some cases, 1-aryl-5-alkyl/arylpyrazole derivatives resulted from these reactions as minor products. In conclusion, 4-iodopyrazole derivatives were synthesized for the first time directly from acyclic starting materials, ,-acetylenic phenylhydrazones and iodine, via electrophilic cyclization.
5
Cottineau, Bertrand. "Contribution à l'étude du 3-hydroxy-1H-pyrazole-4-carboxylate d'éthyle : application à la synthèse de composés antidiabétiques." Orléans, 2002. http://www.theses.fr/2002ORLE2014.
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Le diabète est l'affection endocrinienne de loin la plus fréquente. Il touche environ deux millions de personnes en France et se caractérise par une élévation de la concentration plasmatique en glucose et triglycérides. Cette hyperglycémie chronique contribue à l'apparition de complications spécifiques. Dans le cadre d'une recherche de nouveaux agents antidiabétiques, nous avons préparé à partir d'un synthon commun, le 3-hydroxy-1H-pyrazole-4-carboxylate d'éthyle, des composés diversement fonctionnalisés notamment en position 1 et 3 via des réactions de O et N-alkylations régiospécifiques, et en position 5 via des réactions de couplage catalysées au palladium (0). Par la suite, la mise au point des réactions de type ± Eenie-Meenie α à partir du (3-méthoxy-1-méthyl-1H-pyrazol-4-yl)-méthanol a permis la synthèse de 4-benzylpyrazoles. Les tests pharmacologiques, effectués par la société Merck-Santé, ont montré que certains composés synthétisés présentent une bonne activité hypoglycémiante.
6
Kivrak, Arif. "Development Of New Methods For The Synthesis Of Pyrazoles, 4-iodopyrazoles, Isoxazoles And 1,2,4-oxadiazoles." Phd thesis, METU, 2011. http://etd.lib.metu.edu.tr/upload/12612945/index.pdf.
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Synthesis of five-membered heteroaromatic compounds such as pyrazoles, isoxazoles and 1,2,4-oxadiazoles are important for pharmaceutical industry and material science due to their applications. Although there are many methods to prepare such compounds, new variants continue to appear since they exhibit a wide range of biological and medicinal activities.
In this thesis, new methods were developed for the synthesis of 4-iodopyrazoles, pyrazoles, isoxazoles, 1,2,4-oxadiazoles and/or 1,2,4-oxadiazepines. In the first part of the study, electrophilic cyclization of &alpha,&beta
-alkynic hydrazones by molecular iodine and copper iodide were investigated as new ways for the synthesis of 4-iodopyrazoles and pyrazoles, respectively. Initially, &alpha
,&beta
-alkynic hydrazones were prepared by the reactions of propargyl aldehydes and ketones with hydrazines. Then &alpha
,&beta
-alkynic hydrazones were treated with molecular iodine in the presence of NaHCO3, which afforded 4-iodopyrazoles in good to excellent yields. Subsequently, the same reactions were carried out with CuI in the presence of NEt3, which furnished corresponding pyrazoles in good yields. Moreover, ferrocenyl-substituted 4-iodopyrazoles and pyrazole derivatives were synthesized from corresponding
7
Toto, Patrick. "Contribution à l'étude du 1H-pyrazole-4-carboxylate d'éthyle et de ses dérivés : application à la synthèse de nouveaux hétérocycles polycondensés." Orléans, 2004. http://www.theses.fr/2004ORLE2001.
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Le Diabète est une affection due à une déficience des mécanismes de régulation de la glycémie, dont la fréquence a augmentée de façon régulière et significative au sein des pays riches occidentaux durant les trente dernières années. Les hypoglycémiants de synthèse sont employés dans le cadre du traitement du Diabète non insulino-dépendant. Afin de synthétiser de nouvelles molécules hypoglycémiantes, des méthodologies de fonctionnalisation du 1H-pyrazole-4-carboxylate d'éthyle ont été développées à partir des 3 et 5 aminopyrazole-4-carboxylate d'éthyle. Dans un premier temps les positions 3 et 5 ont été halogénées par diazotation ou substitution électrophile. Les halogénopyrazoles obtenus ont permit d'accéder à divers pyrazoles tétrasubstitués par métallation, couplage ou SNar. Dans un deuxième temps des pontages N1-C5, C3-C4, C4-C5 ont conduit à de nouveaux hétérocycles polycondensés tel que les thiéno[2,3c]pyrazoles ou les 4-thia-1,8a-diaza-azulènes obtenus par métathèse.
8
Desalegn, Nebiyou. "Kinetic Studies Of The Thermolysis Of 3-Halogenated-4,5-Dihydro-3h-Pyrazoles." Digital Archive @ GSU, 2005. http://digitalarchive.gsu.edu/chemistry_theses/1.
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3-Chloro-4,4,5-trimethyl-3,5-diphenyl-4,5-dihydro-3H-pyrazole (3b) and 3-bromo-4,4,5-trimethyl-3,5-diphenyl-4,5-dihydro-3H-pyrazole (3c) were prepared for the thermolysis project. The thermal decompositions of 3b and 3c were monitored using 1H NMR spectroscopy. Plots of ln (% starting material) vs. time (sec) were linear for at least two half lives and the first order rate constants were determined over at least a 30o temperature range. The relative reactivity was found to be 3c > 3b. The activation parameters determined for the thermal decomposition of the pyrazoline at 150oC were found to be: for 3b &#;H‡ = 33 &#;1.0 kcal/mol, &#;S‡ = -2.4 &#; 0.07eu , k150 0 = 7.34 &#; 0.44 x 10 -5 s-1 ; for 3c &#;H‡ = 30&#;0.2 kcal/mol, &#;S‡ = -6.9 &#;0.03 eu, k150o = 42.3&#;0.7 x 10-5 s-1. Thermal decomposition of 3b both neat and in dibromobenzene (DBB) resulted in the formation of an intermediate 2,3-diphenyl-4-methyl-1,3-pentadiene (8) as a major product and minor isomers of 8. These intermediates then thermally decomposed to 1,1,3-trimethyl-2-phenyl-1H-indene (9) via an acid catalyzed process. In order to gain a mechanistic understanding (ionic vs. radical pathways) of the thermal decomposition of 3b, a product study was conducted in protic solvents. In methanol and ethanol, 3b underwent an ionic reaction (SN1-type) with the solvent to produce 3-methoxy/ethoxy-4,4,5-trimethyl-3,5-diphenyl-4,5-dihydro-3H-pyrazole (3/3d) in good yield. The reaction of 3b with refluxing protic solvents led to the development of new method for the synthesis of alkoxy-4,5-dihydro-3H-pyrazoles which is both safe and efficient.
9
Piovesan, Luciana Almeida. "Síntese de novos heterociclos a partir do ácido levulínico." Universidade Federal de Santa Maria, 2009. http://repositorio.ufsm.br/handle/1/4233.
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Conselho Nacional de Desenvolvimento Científico e TecnológicoThe synthesis of new compounds alkyl 3-azolyl propanoate e alkyl 3-azolyl propanoic acid structurally analogues to gamma-aminobutiric acid (GABA) is reported. One more time using the acetal acylation method, now the acetal derivative of 4-oxopentanoic acid (levulinic acid), the methyl 4,4- dimethoxypentanoate, were obtained the precursors methyl 7,7,7-trifluoro[chloro]-4- methoxy-6-oxo-heptenoates, 1,3-dieletrophilic precursor with alcanoate substituent. Are presented efficient and regioespecific synthetic routes from reactions of cyclocondensation [3+2] among 1,3-dieletrofilic precursors with hydroxylamine and different hydrazines, until training isoxazoles and pyrazoles, functionalized with the side chain alkyl propanoate or propanoic acid. Simultaneously to the formation of heterocycles, were studied the hydrolysis reaction of trichloromethyl group and transesterification reaction of methyl propanoate, in the same reactional medium. All products are novel, presenting a good to excellent yields, high purity and the structures were assigned by 1H NMR, 13C NMR and mass spectrometry.
A síntese de novos compostos 3-azolil-propanoatos de alquila e 3-azolilácidos propanóicos, análogos estruturalmente ao ácido gama-aminobutírico (GABA) é relatada. Novamente aplicando o método de acilação de acetais, agora ao acetal derivado do ácido 4-oxopentanóico (ácido levulínico), o 4,4-dimetoxipentanoato de metila, foram obtidos os precursores 7,7,7-triflúor[cloro]-4-metoxi-6-oxo-heptenoatos de metila, precursores 1,3-dieletrofílicos com o substituinte alcanoato. São apresentadas rotas sintéticas eficientes e regioespecíficas a partir de reações de ciclocondensação [3+2] entre os precursores 1,3-dieletrofílicos, com hidroxilamina e hidrazinas diferentes, até a formação de isoxazóis e pirazóis, funcionalizados com a cadeia lateral propanoato de alquila ou ácido propanóico. Simultaneamente à formação dos heterociclos, foram estudadas as reações de hidrólise do grupamento triclorometila e hidrólise ou transesterificação do propanoato de metila, no mesmo meio de reação. Todos os produtos obtidos são inéditos, apresentando rendimentos de bons a excelentes e pureza alta e suas estruturas foram atribuídas por RMN1H e 13C e por espectrometria de massas.
10
Oleksik, Laurence. "Methodology for the synthesis of 4 or 5-substituted-3-perfluoroalkyl pyrazoles." Thesis, University of Leicester, 2004. http://hdl.handle.net/2381/30087.
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Initially the perfluoroacylation of a range of commercially available vinyl ethers and conversion of the resulting perfluoroacylated enol ethers to 1-H-pyrazoles via reaction with hydrazine is reported. The selective synthesis of a range of alpha-aryl vinyl ethers using Heck chemistry is then reported. Subsequent perfluoroacylations of the vinyl ethers followed by reaction of the resulting perfluoroacyl enol ethers with hydrazine affords a range of 5-aryl-3-perfluoroalkyl pyrazoles in good yields.;Alternative methodology for the synthesis of 5-aryl-3-perfluoroalkyl pyrazoles is then described in which resin bound esters are converted to vinyl ethers
11
Panasenko, N. V. "Synthesis and fluorescence spectrum of 9-(4-pyrazolyl)decahydroacridindiones-1,8." Thesis, БДМУ, 2022. http://dspace.bsmu.edu.ua:8080/xmlui/handle/123456789/19545.
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Moiseev, Andrey G. "Synthesis and photochemistry 3,5-dialkyl-3,5-dihydro--3,5-diphenyl-4H-pyrazol-4-ones." Bowling Green, Ohio : Bowling Green State University, 2006. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=bgsu1134948701.
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Oliveira, Lanussy Porfiro de. "Atividade analgésica, anti-inflamatóriae vasorelaxante de dois derivados pirazólicos: 5-[1-(4- fluorfenil)-1H-pirazol-4-IL]-2H-tetrazola(LQFM 020) e 5- [1-(2-fluorofenil)-1H-pirazol-4-IL]-2H-tetrazola (LQFM 039)." Universidade Federal de Goiás, 2014. http://repositorio.bc.ufg.br/tede/handle/tede/4876.
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Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPES
Inflammation is a complex process that aims to protect the body eliminating the harmful agent and to promote tissue repair is characterized by classic signs: pain, heat, redness and swelling as a result of failure to resolve the inflammatory process may occur loss of function. Control of pain and inflammation leads to the search for new drugs both analgesic and antiinflammatory drugs with good efficacy to aid in the treatment of these deseases. The aim of this study was to evaluate the pharmacological effects of two pyrazole derivatives. In acute nociception tests LQFM 020 (9, 17.5 and 35 mg/kg) and LQFM 039 (17.5, 35 and 70 mg/kg) reduced the number of writhing dose dependent manner to 53, 48 and 35; and 57, 52, 42, respectively, while the control group the number of writhes was 88. In the formalin test this antinociceptive effect was confirmed by the reduction in time reactivity to pain in both test phases, the time in the control group was 78 and 72s in the first phase and 150 and 128s in the second phase, with LQFM for 020 and 039 LQFM in the first phase was to reduce 50 and 47s and the second phase to 97 and 74s respectively. In bending the tail the groups of mice treated with LQFM 020 and LQFM 039 test were not able to increase the latency to thermal stimulus demonstrated that the analgesic effect does not involve central mechanisms. Furthermore, the results of the enzymatic activity of cyclooxygenase (COX) and phospholipase (PLA2) in vitro tests indicated no part of the mechanism of action involved in the activity of these compounds. In vascular reactivity tests LQFM 020 promoted vasorelaxant effect presenting maximum effect (Emax) of 93% in aortic preparations with endothelium and maximum effect (Emax) of 91% without endothelium . LQFM 039 also promoted vasorelaxant effect with maximum effect (Emax) of 80% when tested in preparations with endothelium and maximum effect (Emax) of 76% without endothelium, given this result, we investigated the mechanism of action of these compounds. Our results showed that LQFM 020 and LQFM 039 demonstrated the involvement of NO/cGMP pathway and suggest also the involvement of sensitive Ca2+ channels in the plasma membrane voltage.
A inflamação é um processo complexo que tem como objetivo proteger o organismo, eliminando o agente lesivo, e promover a reparação tecidual sendo caracterizada por: dor, calor, rubor, edema e como consequência da não resolução do processo inflamatório pode ocorrer a perda da função. O controle da dor e inflamação leva a busca por novos fármacos tanto analgésicos quanto anti-inflamatórios com boa eficácia para auxiliar no tratamento destas doenças. O objetivo desse trabalho foi avaliar os efeitos farmacológicos de dois derivados pirazólicos. Nos testes de nocicepção aguda, LQFM 020 (9, 17,5 e 35 mg/kg) e LQFM 039 (17,5, 35 e 70 mg/kg), reduziram o número de contorções abdominais de maneira dose dependente para 53, 48 e 35 e para 57, 52 e 42, respectivamente, enquanto que no grupo controle o número de contorções foi de 88. No teste da formalina este efeito antinociceptivo foi confirmado com a redução no tempo de reatividade à dor nas duas fases do teste, o tempo no grupo controle foi de 78 e 72s na primeira fase e de 150 e 128s na segunda fase sendo que para LQFM 020 e LQFM 039 na primeira fase a redução foi para 50 e 47s e na segunda fase para 97 e 74s respectivamente. No teste de flexão de cauda os grupos de camundongos tratados com LQFM 020 e LQFM 039 não aumentaram a latência ao estímulo térmico demonstrando que o efeito analgésico não envolve mecanismos centrais. Os resultados dos testes de atividade enzimática de cicloxigenase (COX) e fosfolipase (PLA2) in vitro sugere que a inibição destas enzimas não faz parte do mecanismo de ação envolvido na atividade desses compostos. Nos testes de reatividade vascular LQFM 020 promoveu efeito vasorrelaxante apresentando efeito máximo (Emax) de 93% em preparações de aorta com endotélio e efeito máximo (Emax) de 91% sem o endotélio. LQFM 039 também promoveu efeito vasorrelaxante com efeito máximo (Emax) de 80% quando testadas em preparações com endotélio e efeito máximo (Emax) de 76% sem o endotélio, dado este resultado, foi investigado o mecanismo de ação desses compostos. Os resultados mostraram que LQFM 020 e 039 LQFM demonstram o envolvimento da via NO / GMPc e também sugerem o envolvimento de canais de Ca2+ sensíveis à voltagem na membrana plasmática.
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Panasenko, N. V., and М. K. Bratenko. "Synthesis of 3-(3-aryl-1-phenyl-1H-4-pyrazolil)-chromen-2-ones." Thesis, БДМУ, 2017. http://dspace.bsmu.edu.ua:8080/xmlui/handle/123456789/16864.
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CHAOUI, ROQUAI M'HAMMED. "Extraction d'indium (iii) en milieu chlorure par le 3-phenyl-4-benzoyl-5-hydroxy-isoxazole. Synergies. Comparaisons avec les 4-acyl-5-hydroxy-pyrazoles." Université Louis Pasteur (Strasbourg) (1971-2008), 1995. http://www.theses.fr/1995STR13134.
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Ce travail traite de l'extraction d'indium (iii) a partir du milieu chlorure par le 3-phenyl-4-benzoyl-5-hydroxy-isoxazole (hpbi) associe a des agents de synergie tels l'oxyde de tri-n-octylphosphine (topo) ou le chlorure de tri-n-octylammonium (tomacl). Une interaction forte entre hpbi et topo a ete mise en evidence par differentes techniques spectroscopiques (rmn du #1h, #1#3c, #3#1p, ir et uv). Les formes tautomeres de hpbi dans les divers solvants d'extraction ont ete determinees. Dans les extractions synergiques, des especes mixtes ont ete mises en evidence: incl#x(pbi)#3#-#x(topo)#2 (x = 0 a 3) ou toma. Incl#2(pbi)#2. Ces extractions sont comparees a celles obtenues par les monoacylpyrazolols et par les bis(acylpyrazolols) hl-n-lh. Dans ce dernier cas, on observe un repli de la chaine polymethylene sur le centre metallique, ce qui confere aux complexes formes: toma. Incl#2(l-n-l) ou incl(l-n-l)(topo)#2 une grande stabilite. L'extraction par ces bis(chelatants) seuls implique la formation d'une espece unique in(l-n-l)(l-n-lh), n = 8, 12 ; pour n =4, l'espece dimere in#2(l-4-l)#3 est egalement observee. L'ordre d'efficacite est: hl-8-hl>hl-4-lh>hl-12-lh
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GUIGUEMDE, ISSAKA. "Transfert d'ions metalliques divalents entre phases liquides par des bis(5-hydroxy-pyrazol-4-oyl) alcanes; selectivite." Université Louis Pasteur (Strasbourg) (1971-2008), 1992. http://www.theses.fr/1992STR13178.
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Les extractions de metaux divalents m#2#+ (m=cd, zn, cu) par les bis(5-hydroxy-pyrazol-4-oyl) alcanes hl-n-lh (n: nombre de maillons methylene), ainsi que par ces extractants en presence de tri-n-octylphosphine (topo) a partir de milieux aqueux perchlorates, ont ete etudiees. En ce qui concerne le cuivre, les complexes extraits sont: cu(l-n-l) pour n8, des dimeres et des oligomeres pour n<8, et dans quelques cas rares, des complexes cu(l-n-lh)#2. Le topo n'a pas d'influence sur l'extraction du cuivre. Avec le zinc, les especes extraites sont zn(l-n-l) (n5) et zn(l-n-l) (topo) dans le 1,2-dichloroethane. Dans le chloroforme, on obtient les complexes zn(l-n-l) (n=9 et 10), zn(l-n-lh)#2 (n=7 et 8) et, en presence de topo, zn(l-n-l)(topo) (n7), et zn(l-n-lh)#2(topo) (n=5 et 7). Le cadmium, qui a un rayon ionique plus grand, donne des complexes cd(l-n-l)(topo)#2, cd(l-8-l)(topo) et cd(l-8-lh)#2(topo). L'extraction du cuivre par le meta-bis(5-hydroxy-pyrazol-4-oyl) benzene hl-ph-lh a aussi ete etudiee: les complexes cu(l-ph-lh)#2 et cu#2(l-ph-l)#2 sont extraits dans le chloroforme. Nous avons recherche la coextraction eventuelle des couples zn-co, zn-cd et zn-cu en etudiant leur extraction simultanee a partir de la meme phase aqueuse. La selectivite d'extraction de ces metaux n'est en fait pas affectee
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Bensliman, Chakib. "Von Alpha,Beta-ungesättigten Ketonen und ihren Oximen zu Pyrazol-4-on-1,2-dioxiden, potentiellen NO-Pharmaka /." [S.l. : s.n.], 1998. http://www.gbv.de/dms/bs/toc/253245788.pdf.
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Liebold, Claudia. "Immobilisierung von Palladium mittels 1,4-Bis-(4‘-pyrazolyl)benzen und dessen Anwendung in der heterogenen Katalyse." Doctoral thesis, Technische Universitaet Bergakademie Freiberg Universitaetsbibliothek "Georgius Agricola", 2013. http://nbn-resolving.de/urn:nbn:de:bsz:105-qucosa-124709.
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Die Immobilisierung homogener Katalysatoren ist eine wichtige Methode zur Realisierung der Abtrennbarkeit und Wiederverwendbarkeit aktiver Spezies. Im Rahmen dieser Arbeit wurde durch die Komplexierung von Palladium mit 1,4-Bis-(4′-pyrazolyl)benzen ein neues mikroporöses Koordinationspolymer generiert und dieses als heterogener Katalysator in der Suzuki-Miyaura-Kreuzkupplungsreaktion erfolgreich eingesetzt. Dabei konnten vollständige Umsätze und hohe Selektivitäten erzielt werden, die vergleichbar zu bereits kommerziell erhältlichen homogenen Katalysatoren sind. Die Besonderheit des Katalysators ist, neben dessen außergewöhnlich hohen chemischen Stabilität, die Variation seiner Struktureigenschaften durch die Wahl der Synthesebedingungen und die damit verbundene Steuerung seiner katalytischen Aktivität.
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Do, Khoa Quang. "Design, Synthesis and Binding Studies of Trisubstitutedpyrazolo[3,4-d]pyrimidines." Thesis, Griffith University, 2006. http://hdl.handle.net/10072/367533.
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Pyrazolo[3,4-d]pyrimidines were known as adenosine antagonists at the rat A1 and A2A adenosine receptors based on our previous studies. In this study, 245 pyrazolo[3,4-d]pyrimidines derivatives with various benzyl substitutents at N-1 and various hydrophobic side chains at C-4 and C-6 were synthesized and screened at the human A1, A2A and A3 adenosine receptors. 14 out of 245 compounds were resynthesized and purified to determine the Ki values of these compounds at the human A1 adenosine receptor. Chapter 1 of the thesis is a literature review of adenosine research. It describes the physiology of adenosine and the discovery and characterization of all adenosine receptors namely A1, A2A, A2B and A3. It also looks at the medical application of adenosine, adenosine analogs, adenosine agonists and adenosine antagonists. The final part of the chapter discusses the discovery and development of adenosine agonists and antagonists. Chapter 2 of the thesis describes the rational design of the pyrazolo[3,4-d]pyrimidines template using ligand-based molecular modelling technique and describes the synthesis of the template.
Chapter 3 and chapter 4 describe the application of silicon chemistry and attempts to synthesise a series of pyrazolo[3,4-d]pyrimidines heterocycle by solid phase synthesis. Chapter 5 and chapter 6 describe the synthesis of a series of pyrazolo[3,4-d]pyrimidines heterocycle using the solution phase parallel synthesis and the binding studies of a library of 245 compounds and the resynthesis of 14 target compounds. Chapter 7 describes the cell culture and membrane preparation of the human A1, A2A, A2B and A3 adenosine receptors and radioligands binding assays.Thesis (PhD Doctorate)
Doctor of Philosophy (PhD)
School of Science
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ARICHI, JAOUAD. "Extraction liquide-liquide de terres rares par des 4-acyl-5-hydroxy-pyrazoles et -isoxazoles equilibres et cinetique de transfert. Synergies." Université Louis Pasteur (Strasbourg) (1971-2008), 1998. http://www.theses.fr/1998STR13007.
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L'extraction liquide-liquide de terres rares trivalentes (ln#3#+) a partir du milieu nitrate par des 4-acyl-5-hydroxy-pyrazoles, -ceto-enols notes ha, a ete etudiee. L'extraction croit avec le numero atomique croissant de ln et avec l'acidite croissante de ha, mais aux depens de la selectivite. La presence d'un agent de solvatation, s, associe a ha, de type o-donneur tel l'ether-couronne dibenzo-18-couronne-6 ou de type n-donneur comme la 2,4,6-tri(2-pyridyl)-1,3,5-triazine (tpytz) provoque un effet synergique important, avec l'extraction de complexes lna#3s, selon l'ordre db18c6 << tpytz. Par contre la selectivite d'extraction est reduite particulierement pour les terres rares les plus lourdes. Cependant, pour les systemes impliquant les 4-acyl-5-hydroxy-isoxazoles et la tpytz, l'ordre de la selectivite d'extraction est celle de la complexation des terres rares par la tpytz. Ce resultat est prometteur pour une separation intergroupe lanthanides (iii)/actinides (iii) contenus dans les combustibles nucleaires, les actinides (iii) etant mieux complexes par la tpytz. Le transport de cuivre et des terres rares par des 4-acyl-5-hydroxy-pyrazoles ou isoxazoles a travers une membrane liquide epaisse a ete realisee. Celui-ci est assure par le gradient de ph etabli entre les phases aqueuses d'entree et de sortie de la membrane. A forte vitesse d'agitation, un regime mixte diffusionnel-cinetique est observe. L'etape cinetique lente, pour laquelle differentes lois de vitesse apparentes ont ete etablies et discutees, est localisee a l'interface d'entree de la membrane. Le flux de sortie est toujours limite par la diffusion des especes cua#2 et lna#3 a travers la couche organique non agitee de l'interface de sortie.
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Bacher, W. [Verfasser]. "Zur Reaktion von 4-Acylsubstituiertem 1-Phenyl-3-methyl-pyrazolon-5 mit Actinidenionen in waessriger Loesung / W. Bacher." Karlsruhe : KIT-Bibliothek, 2009. http://d-nb.info/118690495X/34.
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Liebold, Claudia [Verfasser], Florian [Akademischer Betreuer] Mertens, Florian [Gutachter] Mertens, and Roger [Gutachter] Gläser. "Immobilisierung von Palladium mittels 1,4-Bis-(4‘-pyrazolyl)benzen und dessen Anwendung in der heterogenen Katalyse : Immobilisierung von Palladium mittels 1,4-Bis-(4‘-pyrazolyl)benzen und dessen Anwendung in der heterogenen Katalyse / Claudia Liebold ; Gutachter: Florian Mertens, Roger Gläser ; Betreuer: Florian Mertens." Freiberg : Technische Universitaet Bergakademie Freiberg Universitaetsbibliothek "Georgius Agricola", 2013. http://d-nb.info/1220911631/34.
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HEMONIC, DANIELE. "Etude cinetique et thermodynamique de l'extraction du cuivre par la 1-phenyl-3-methyl-4-stearoyl-pyrazol-5-one : comparaison a d'autres extractants." Paris, ENMP, 1987. http://www.theses.fr/1987ENMP0156.
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Etude de l'extraction du cuivre en milieu sulfate par une pyrazolone diluee dans le solvesso 150. Determination des constantes d'equilibre et de cinetique d'extraction, utilisation d'un modele thermodynamique
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Hemonic, Danielle. "Etude cinétique et thermodynamique de l'extraction du cuivre par la 1-phényl-3-méthyl-4-stéaroyl-pyrazol-5-one comparaison à d'autres extractants /." Grenoble 2 : ANRT, 1987. http://catalogue.bnf.fr/ark:/12148/cb376059420.
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Hlimi, Fouzia. "Cycloaddition de diarylnitrilimines sur des dérivés de la benzodioxine 1,4 et de la benzoxazine-1,4 : regiochimie de la réaction sur un alcene portant un groupe donneur et un groupe accepteur sur la même extrêmité." Besançon, 1987. http://www.theses.fr/1987BESA2018.
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La cycloaddition dipolaire 1,3 des diarylnitrilimines sur le benzodioxinne-1,4 carboxylate-2 d'ethyle conduit a des cycloadduits qui apres ouverture donnent des derives de l'aryloxy-4 diphenyl-1,3 pyrazole qui ne sont pas accessibles par une methode classique de synthese de pyrazoles
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Tuloup, Rémy. "Addition du diazomethane aux thiazabutadienes : une application du cycle pyrazoline a la synthese multi etapes d'amino-7 formyl-4 cephemes." Rennes 1, 1988. http://www.theses.fr/1988REN10029.
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Sahmoune, Amar. "Extractions synergiques de metaux divalents de transition par association d'une acyl-4-pyrazolone-5 avec des polyethers cycliques et acycliques." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13116.
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Extractions de co. Zu. Cd et cu divalents par les melanges phenyl-1 methyl-3 benzoyl-4 pyrazolone-5 ethers crown. La coextraction alcalins-alcalinoterreux complexes par les composes crown et des metaux divalents est possible quand la taille de la cavite de l'ether-crown est voisine de celle de l'alcalin (ou alcalino-terreux) et quand l'ion ml::(3)**(-) est suffisamment stable
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Sahmoune, Amar. "Extractions synergiques de métaux divalents de transition par association d'une acyl-4-pyrazolone-5 avec des polyéthers cycliques et acycliques." Grenoble 2 : ANRT, 1988. http://catalogue.bnf.fr/ark:/12148/cb37618386w.
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Tuloup, Rémy. "Addition du diazométhane aux thiazabutadiènes une application du cycle pyrazoline à la synthèse multi-étapes d'amini-7 formyl-4 céphèmes /." Grenoble : ANRT, 1988. http://catalogue.bnf.fr/ark:/12148/cb37619005g.
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Moraes, Paulo Alexandre de. "N-alquilação regiosseletiva de pirazóis empregando 4-alcóxi(amino)-5-bromo-1,1,1-trifluorpent-3-en-2-onas." Universidade Federal de Santa Maria, 2016. http://repositorio.ufsm.br/handle/1/10628.
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This work presents the synthesis of three new series of nitrogen-heterocycles containing the substituent trifluoromethyl, exploiting the synthetic versatility and regioselectivity of 4-alkoxy-5-bromo-1,1,1-trifluorpent-3-en-2-ones and 4-amino-5-bromo-1,1,1-trifluoropent-3-en-2-ones in reactions with compounds containing nucleophilic nitrogen.
Two series of 1-(3-alkoxy-5-trifluoromethyl-2,3-dihydrofuran-3-yl)-4,5-alkyl-3-(trifluoromethyl)-1H-pyrazoles were synthesized by the N-functionalization reaction of pyrazoles with 4-alkoxy-5-bromo-1,1,1-trifluorpent-3-en-2-ones, by Michael s nucleophilic addition. In the first step, there is a nucleophilic addition of the pyrazol molecule to the beta position of enones (Cβ), followed by an intramolecular cyclization reaction, where the furan ring is formed by replacement of the bromine atom by the carbonyl oxygen of enone, resulting in thirteen novel compounds with yields between 55-86%.
The other compounds series, (E)-4-(amino)-1,1,1-trifluoro-5-(5-methyl-3- (trifluoromethyl)-1H-pyrazol-1-yl)pent-3-en-2-ones, was synthesized by N-alkylation reaction, through a bimolecular nucleophilic substitution (SN2) mechanism, with replament of the bromine atom, at five position (Cγ) of 4-amino-5-bromo-1,1,1-trifluoropent-3-en-2-ones, by the nucleophilic nitrogen of the pyrazoline ring. Seven N-alkylated products were obtained, with yields among 65-85%.
In addition, the regioselectivity study of N-functionalized pyrazoles reactions is described, including the evaluation of reaction conditions and how substituents present in the pyrazole structure can influence the product formation, because many different steric and electronic factors.
The obtained compounds were characterized by nuclear magnetic resonance 1H and 13C, mass spectrometry, elementary analysis and X-ray diffractometry.A presente dissertação relata a síntese de três séries inéditas de heterociclos nitrogenados trifluormetil substituídos, que exploram a versatilidade sintética e a regiosseletividade das 4-alcóxi-5-bromo-1,1,1-trifluorpent-3-en-2-onas e das 4-amino-5-bromo-1,1,1-trifluorpent-3-en-2-onas, em reações com nucleófilos nitrogenados. As primeiras duas séries dos compostos 1-(3-alcóxi-5-trifluorometil-2,3-diidrofuran-3-il)-4,5-alquil-3-(trifluorometil)-1H-pirazóis, foram sintetizadas através do processo de N-funcionalização de pirazóis, a partir da reação com as 4-alcóxi-5-bromo-1,1,1-trifluorpent-3-en-2-onas, cujo o caminho mecanístico se deu através de uma reação de adição nucleofílica de Michael. Inicialmente, ocorre a adição do pirazol nucleofílico na posição beta (Cβ) das enonas bromadas, seguida de uma reação de ciclocondensação intramolecular formando o anel furano, com a substituição átomo de bromo pelo oxigênio enólico, resultando na formação de treze compostos inéditos, com rendimentos entre 55 e 86%. Outra série de compostos (E)-4-(amino)1,1,1-triflúor-5-(5-metil-3-(trifluormetil)-1H-pirazóis-1-il)pent-3-en-2-onas, foi sintetizada através da reação de N-alquilacão, via substituição nucleofílica bimolecular (SN2), onde o átomo de bromo na posição cinco (Cγ), das 4-amino-5-bromo-1,1,1-trifluorpent-3-en-2-onas, foi substituído pelo nitrogênio nucleofílico do anel pirazolínico, promovendo a formação de sete produtos N-alquilados, com rendimentos que variam entre 65 e 85%. Além disso, um estudo de regiosseletividade das reações N-funcionalizadas de pirazóis está descrito, onde a avaliação das condições reacionais e também de fatores estéricos e eletrônicos dos substituintes presentes nos substratos, foram determinantes para formação do produto formado. Os produtos obtidos neste trabalho foram caracterizados por ressonância magnética nuclear de 1H e 13C, espectrometria de massas de baixa e alta resolução, análise elementar e difratometria de Raio X.
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Perez-Ruiz, Edgar. "Analyse vibrationnelle et structurale comparée de biomolécules à visée thérapeutique : 1,7 dihydro-6h-purine-6-thione (6-mercaptopurine), 1,5-dihydro-4h-pyrazolo(3,4-d)pyrimidine-4-thione (tisopurine) et leurs chlorures." Montpellier 1, 1997. http://www.theses.fr/1997MON13521.
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Holz, Karsten. "Enol-Konjugate von 1-Phenyl-3-methyl-4-amino-3-pyrazolin-5-on als "minor metabolites" im Stoffwechsel von Metamizo. (Novalgin R) : Untersuchungen zur Analytik, zu Nachweis, Bildung und Verbleib metastabiler Phase-II-Metaboliten bei der Ratte /." [S.l. : s.n.], 1997. http://www.gbv.de/dms/bs/toc/226144828.pdf.
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Kuleshova, Olena. "2-azahetaryl-3-enaminonitriles cycliques pour la synthèse d'azahétérocycles fonctionnalisés, la complexation de métaux et la conception de sondes optiques." Thesis, Toulouse 3, 2018. http://www.theses.fr/2018TOU30127/document.
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Les recherches effectuées au cours de ce travail de thèse sont centrées sur les dérivés cycliques de type 2-azahetaryl-3-énaminonitrile qui représentent une structure d'intérêt du fait de son nombre élevé de sites réactifs potentiels. La fonctionnalisation régiosélective de chaque site donne en effet accès à des une grande diversité structurelle de composés azoté et substitué par un azahétérocycle. Un atout majeur des 2-azahetaryl-2-(1-R-pyrrolidin-2-ylidene)acétonitriles est leur grande accessibilité à partir de matières premières simples et bon marché. Nous avons pu étudier leur emploi dans la synthèse des pyrazoles (isoxazoles). Ils jouent alors le rôle de diélectrophiles 1,3. L'action d'hydrazine (hydroxylamine) conduit à des 5-amino-4- azahetaryl-3-(ω-aminopropyl)-1H-pyrazole (isoxazole) formés avec une régiosélectivité complète et de bons rendements 50-85%. Ceci établit une approche en deux étapes efficace et facilement reproductible à des amino-pyrazoles substitués par des hétérocycles à partir d'acétonitriles hétérocycliques. Des transformations subséquentes ont été réalisées donnant accès à des polyamino-azoles dérivatisés régiosélectivement, à des composés tétracycliques jusqu'à un rendement global de 45% et à des pyrazoles arylés jusqu'à 71% de rendement par diazotation suivie d'une arylation par couplage croisé Suzuki-Miyaura ou C-H activation. Nous avons illustré une protection de l'azote efficace sous forme de nitrosamine pendant le couplage croisé catalysé par Pd. Nous avons également effectué la quaternarisation de l'azote de l'hétérocycle pour étudier l'effet d'une moitié cationique sur la régiosélectivité de la réaction de tels dérivés 2-azahetaryl-3-énaminonitrile avec des 1,2-binucléophiles. L'augmentation de la demande en électrons sur l'hétérocycle a induit un changement de chemin réactionnel qui a conduit à un produit issu de l'ouverture du cycle azole. Une différence de réactivité entre les dérivés du benzoxazole et du benzimidazole d'une part et du benzothiazole d'autre part a été observée. Alors que les premiers suivent la voie d'ouverture de cycle, le second suit une transformation "classique" puis une substitution nucléophile au centre C-2 du benzothiazole conduisant à la formation du cycle de l'azépine. Dans le cas des énaminonitriles substitués par un benzoxazolyle dans les mêmes conditions, les deux régioisomères sont formés. La réaction de formylation du 2-(benzo[d]thiazol-2-yl)-2-(pyrrolidin-2-ylidène) acétonitrile avec le N,N-diméthylformamide diméthylacétal (DMF DMA), suivie d'une amination et d'une cyclisation dans des conditions basiques a engendré à la pyrrolo[3,2-c]pyridine-6-imine, un composé qui présente un rendement quantique fluorescent élevé (Φ = 61%) et s'est révélé très sensible à la protonation. Les deux caractéristiques devraient être utiles pour développer un test de détection d'eau originaux pour les solvants aprotiques. Nous avons démontré qu'une telle méthode fluorométrique pour déterminer la teneur en eau dans le DMSO présente une limite de détection de 0,068%The research carried out in the course of this PhD work is centered on cyclic 2-azahetaryl-3-enaminonitrile derivatives which represent an attractive scaffold due to its high number of potential reactive sites. Regioselective functionalization of each site may give access to various structurally different Nitrogen-containing moieties featuring an azaheterocycle substituent. One first application in heterocyclic synthesis of 2-azahetaryl-2-(1-R-pyrrolidin-2-ylidene)acetonitriles, readily accessed from available and cheap starting materials, is their involvement in Knorr-type synthesis of pyrazoles (isoxazoles) where they play the role of the 1,3-dielectrophiles. Thus 4-azahetaryl-3-(ω-aminopropyl)-1H-pyrazole (isoxazole)-5-amines are formed with complete regioselectivity in good yields 50-85%. This establishes an efficient and easily reproducible two-step approach to heterocycle- substituted amino-pyrazoles from heterocyclic acetonitriles. Unprecedented subsequent transformations were carried out providing an access to regioselectively derivatized polyamino azoles, tetracyclic compounds in up to 45% overall yield and arylated pyrazoles in up to 71% yield through diazotization, followed by arylation through Suzuki-Miyaura cross-coupling or C-H activation. We illustrated the unprecedented but efficient nitrogen protection as a nitrosamine during the Pd-catalyzed cross-coupling. Also the possibility of pyrazoles C-H activation in order to get densely substituted pyrazoles was shown for the first time. We also performed the quaternarization of the nitrogen of the heterocycle to investigate the effect of a cationic moiety on the regioselectivity of the reaction of such azahetaryl-3-enaminonitrile derivatives with 1,2-binucleophiles. The increased electron demand on the heterocycle induced a reaction path shift that produced the azole ring- opened product. Derivatives of benzoxazole and benzimidazole form second way products straight away, while the one of benzothiazole undergoes the "classical" transformation pathway and subsequent nucleophilic substitution at C-2 center of benzothiazole leading to azepine cycle formation. In the case of benzoxazolyl substituted enaminonitriles under the same conditions both regioisomers are formed. Formylation reaction of 2-(benzo[d]thiazol-2-yl)-2-(pyrrolidin-2-ylidene) acetonitrile with N,N-dimethylformamide dimethyl acetal (DMF DMA), followed by further reamination and cyclization under basic conditions gave rise to pyrrolo[3,2-c]pyridine-6-imine, a compound that exhibits a high fluorescent quantum yield (Φ = 61%) and proved to be very sensitive to protonation. Both characteristics are expected to be useful to develop an unprecedented water detection test for aprotic solvents. We have demonstrated that such a fluorometric method for determining water content in DMSO presents a limit of detection of 0.068%. From other enaminonitriles reactions with DMF DMA provided either a mixture of methylated and formylated products, or only methylated products (few adducts also shown non reactivity). These observations prompted us to assume that the presence of easily accessible NH group is essential in formylation of the C-3 center of pyrrolidine allowing to propose a mechanism for this uncommon reaction. 2-Azahetaryl-2-(pyrrolidin-2-ylidene)acetonitriles and their 3-oxo-benzo- analogues were also used to create: a) visible spectrophotometric probes for Zn(II) b) water stable BF2-rigidified complexes that overcome the limitations of BODIPY-dyes and have Stokes shifts up to 9000 cm-1, emission at violet-blue range, fluorescence both in solution (Φ up to 90%) and crystalline state; c) films of polymeric composites exhibiting photovoltaic effect
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Ciccolini, Cecilia. "Synthesis of Mono and Poly-Heterocycles starting from 1,2-Diaza-1,3-Dienes (or precursors) as Building Blocks." Doctoral thesis, Urbino, 2020. http://hdl.handle.net/11576/2674162.
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RIFI, EL HOUSSEINE. "Extraction metallique par des gels hydrophobes." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13158.
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Etude de l'extraction liquide-gel de cu, v et eu. On montre que les lois de la thermodynamique d'extraction de cu par les acyl-4 pyrazolones-5 ne sont pas pertubees par la presence du polymere, mais que la cinetique l'est fortement. L'impregnation des polybutadienes par la trilamylamine presente des difficultes; l'utilisation de pvc gonfle dans des solutions d'oxyde d'octylphenyl n,n-diisobutylcarbamoylmethylphosphine dans tbp est interessante
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LAKKIS, ZAHREDDINE ZEINAB. "Aspects thermodynamiques et cinetiques de l'extraction de metaux divalents par des acyl-4-pyrazolones-5." Strasbourg 1, 1986. http://www.theses.fr/1986STR13001.
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Extraction de cd et zn a partir des milieux aqueux, perchlorate, nitrate et sulfate par des melanges de phenyl-1 methyl-3 benzoyl-4 pyrazolone-5 et de sels d'ammonium lipophiles. Le pyrazolonate de nh::(4) est l'agent reel de synergie. Mecanisme de transport de cuivre par des acyl-4 pyrazolones-5 a travers une membrane liquide epaisse
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Metabanzoulou, Jean-Pierre. "Mecanisme de la complexation de l'ion uo : :(2)**(2+) par des di(acyl-4 pyrazolones-5), des ethers-couronnes, des diazapolyoxamacrocycles et des ligands apparentes." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13146.
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Etude spectrophotometrique de la stabilite des complexes de l'ion uo::(2)**(2+) et de l'ion cu**(2+), dans l'eau et eau-acetonitrile. Structures possibles des complexes 1:1, 1:2 et 2:1. Mecanismes de formation des complexes
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Diantouba, Bertin Aimé. "Effets structuraux des acyl-4-pyrazolones-5 dans l'extraction liquide-liquide des cations metalliques divalents." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13093.
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Etude de l'effet de l'acidite de la lipophilie et effets structuraux des acyl-4 pyrazolones-5 dans l'extraction de cu, co, zu et pb divalents. Extraction de 3 types de complexes metalliques : mononucleaires de type m(l-n-lh)::(2) ou m(l-n-l) et polynucleaires (m(l-n-l))::(j). Meilleures possibilites des bis-acyl-4 pyrazolones-5
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Marouani-Keraghel, Saïda. "Reduction electrochimique de composes d'uranyle en milieu organique." Université Louis Pasteur (Strasbourg) (1971-2008), 1988. http://www.theses.fr/1988STR13175.
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Etude de la reduction chimique de sels (nitrate et acetate) d'uranyle et des complexes (phenyl-1 methyl-3 acyl-4 pyrazolones-5) et beta-cetophosphonates d'uranyle en milieu organique et en presence de perchlorate d'ammonium sur une electrode de mercure
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洪讚誠. "Synthesis and thermal reaction of dimethyl-3, 3-cyclopentyl-3H-pyrazole-4, 5-dicarboxylate." Thesis, 1998. http://ndltd.ncl.edu.tw/handle/46555386938756761561.
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碩士靜宜大學
應用化學研究所
86
Thermolysis of dimethy1-3,3-cyclopentyl-3H-pyrazole-4,5-dicarboxylate(20) afforded dimethy1-4,5,6,7-tetrahydroindazole-2,5-dicarboxylate(24) and dimethy1-1,5-tetramethylene-pyrazole-3,4-dicarboxylate(25) in 69% and 8%, respectively. The mechanism of this reaction is suggested to undergo two competitive pathways. (1)After heating the compound 20 can undergo ring expansion(1,5-sigmatropic migration), i.e. the cyclopentyl group can ring-expand form C3 to N2 to form the compound. 25. (2) Alternatively, the cyclopentyl group of the compound 20 can undergo ring expansion from C3 to C4, and the ester group at C4 can simultaneously migrate to N2(1,5-anticlockwise) to form the compound 24. The activation energy of the thermal reaction of compound 20 was measured be 8.6kcal/mole.k
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Chen, Yin-Ju, and 陳胤儒. "Pyrazole and Triazole Functionalized Calix[4]arenes as Highly Selective Fluorogenic Sensors for Sliver (I) and Mercury (II)." Thesis, 2013. http://ndltd.ncl.edu.tw/handle/82766858787652129622.
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碩士國立交通大學
應用化學系碩博士班
101
Azole heterocycles are interesting compounds because many of them are with biological activities and the azole ligands have been widely used in coordination chemistry. Pyrazoles have attracted considerable interest as ligands, because their conjugate bases, pyrazolates, have been found to bind metal ions in a variety of coordination modes. In this thesis, we report the synthesis of a pyrazolyl methylpyrene functionalized calix[4]arene 35 and a 1,3-alternate calix[4]arene 41 with pyrazolyl methylpyrene on the one end and triazolylphenyl on the other end. Metal ion binding abilities of 35 and 41 were invesitigated by UV-vis, fluorescence, and 1H-NMR spectroscopy. Using UV-vis and fluorescence spectra for screening, we found both 35 and 41 show a strong excimer emission as a free ligand, however, they showed a high selectivity toward Ag+ and Hg2+ ions with strong fluorescent quenching in CHCl3/MeOH (v/v = 3/1), respectively. Compound 35 showed 95% quenching of fluorescence by Ag+ and 97% quenching of fluorescence intensity by Hg2+, and compound 41 showed 41% quenching of fluorescence by Ag+ and 93% quenching of fluorescence intensity by Hg2+. Furthermore, the Job Plot and 1H-NMR titration experiment showed that the binding ratio of 35 toward Ag+ and Hg2+ were both 1:1 complex, and 41 toward Ag+ and Hg2+ were both 1:2 complex. The binding constant of 35 with Ag+ and Hg2+ was determined by fluorescence quenching to be 3.00 × 104 M-1 and 2.99 × 104 M-1, respectively. While the binding constant of 41 with Ag+ and Hg2+ was determined similarly to be 9.24 × 1011 M-1 and 1.46 × 1012 M-1, respectively. The binding constants of 35 with Ag+ and Hg2+ were also determined using UV-vis method to be 3825 and 2993 M-1, respectively.
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陳孟榆. "Pyrazole Calix[4]arenes as Highly Selective Fluorogenic Sensors for Silver (I) and Mercury (II) and Synthesis of Pillar[5]arene Derivatives." Thesis, 2011. http://ndltd.ncl.edu.tw/handle/04499796060226609005.
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碩士國立交通大學
應用化學系碩博士班
99
This study is divided into two parts. First, two series of lower-rim modified calix[4]arene with pyrazole substituents were synthesized. Using phenyl pyrazole calix[4]arenes as basic synthesis frameworks, we synthesized phenylanthryl pyrazole calix[4]arenes 76 and 77 and control compounds 78 and 79 as fluorogenic ions sensors. Based on the results from UV-Vis, fluorescence and 1H-NMR spectrometry, we found that pyrazole calix[4]arenes 77 and 79 recognized Ag+ and Hg2+ with excellent selectivity in MeOH/CHCl3 (v/v = 4:1), respectively. Compound 77 induced 141% enhancement of fluorescence intensity toward Ag+, and compound 79 showed 51% fluorescence quenching effect toward Hg2+.Furthermore, the complexation of compound 77 with Ag+ and 79 with Hg2+ both showed 1:1 host-guest stoichiometry based on by Job plot obtained from fluorescence and 1H-NMR titration spectra. We also found the binding constants of 77 with Ag+ was (1.12 ± 0.17) × 104 M-1 and 79 with Hg2+ was (1.33 ± 0.20) × 104 M-1.Second, the research was focused on the reaction condition to synthesize pillar[5]arenes. Pillar[5]arenes 38 and 83 were successfully and facile synthesized by cyclization reaction with high yield. These compounds were obtained via borontrifloride etherate catalyzed procedure with 1,4-dialkoxyphenyl monomer and paraformaldehyde under 0.1 M solution. Besides, a synthetic route to difunctional pillar[5]arene 95 was also developed by combining two different monomers with 4:1 ratio using the conditions stated above.
43
Chou, Li-Chen, and 周立琛. "Synthesis and anticancer activity of 1,3,5-substituted selenolo[3,2-c]pyrazole analogues、Synthesis and anticancer activity of hydrophilic phosphate prodrugs of 2-phenyl-4-quinolone derivatives." Thesis, 2009. http://ndltd.ncl.edu.tw/handle/72588313584030324230.
Full textAbstract:
博士中國醫藥大學
藥物化學研究所博士班
97
The purpose of this study is to develop compounds with potential anticancer activity as new drug candidate. This thesis consists of two parts. In the first part, four different skeletons of YC-1 derivatives [furopyrazole derivatives (11-22, 28-36), thienopyrazole derivatives (42-45, 50-53), selenopyrazole derivatives (67-72, 75-77), and indazole derivatives (99−118, 123−128)] were synthesized in order to expand the substance patent’s inclusion of YC-1 and find new candidate with better anticancer activity than YC-1, and constructed their SAR in NCI-H226 and A498 cells. Compound 13 (CLC107), 44 (CLC015), 69 (CLC005), and 127 (CLC802a) were chosen for evaluation against 60 human cancer cell lines (the NCI-60) and COMPARE program analysis, and indicated that four compounds were with great development value since they possessed novel mechanism of action different from existing anticancer drugs. Finally compound 127 was proved to demonstrate anticancer activity similar to YC-1 in animal model, it is thus a new candidate of YC-1 in drug development. In the second part, the problem of 2-phenyl-4-quinolone derivatives in pharmacokinetics is resolved. In order to improve solubility problem, a phosphoric acid was attempted to be attached to 4-ketone of 2-phenyl-4-quinolone, and thus phosphate monosodium salts of 2-phenyl-4-quinolone derivatives were successfully created, which were expected to be applied by po and iv routes in clinics. Among 2-phenyl-4-quinolone derivatives, we focus on compound 8 which demonstrated the most significant antitumor activity. According to the data of Pharmacokinetics, compound 35 was proved to be transformed in vivo to compound 8 (CHM-1). After the assessment of safety pharmacology of compound 35 in enzyme activity assay and receptor binding assay, we predict it is very effective and safe drug while there should not be too many side effects in clinical trials. Besides, it showed excellent antitumor activity in SKOV-3 Xenograft SCID mice model and CT-26 colon adenocarcinoma Balb/c mice orthotopic model. It is confirmed that compound 35 (CHM-1-P-Na) is a drug candidate for further development as a potential anticancer agent in the clinic. We hope this series of compounds can successfully become clinical therapeutic agents which are beneficial to human beings.
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Lee, Kun-Ti, and 李昆諦. "(I) Synthesis of Triphenylenyl Triazole Bridged Bispillar[5]arene as Fluorogenic Sensor of Pyridinium and Imidazolium Cations (II) Pyrene Pyrazole Functionalized Calix[4]arene as Highly Selective Fluorogenic Sensor for Silver (I) and Mercury (II) ions." Thesis, 2017. http://ndltd.ncl.edu.tw/handle/4bbh2q.
Full textAbstract:
碩士國立交通大學
應用化學系碩博士班
105
In this study, we have synthesized triphenylenyl triazole bridged pillar[5]arene dimer, triphenylenyl triazole substituted pillar[5]arene and stilbene triazole bridged pillar[5]arene dimer as compound 37, 41, 47, respectively. Based on the results from UV-Vis absorption spectroscopy and fluorescence emission spectroscopy, compound 37 showed good binding abilities toward pyridinium cations G3-G4 and imidazolium cation G5, and compound 41 showed good binding abilities toward G5 only. But, we won’t study compound 47 furthmore, which fluorescence characteristic vanished after exposured by UV light, because of trans-cis isomerism of stilbene group. According to the more detail research of UV-Vis spectroscopy, fluorescence spectroscopy, Hill plot and 1H NMR titration, we found that binding ability 37•G3 > 37•G5 > 37•G4, which binding constant were 2.21 × 105 M-2, 5.83 × 104 M-2 and 2.12 × 104 M-1, determing by Hill equation. Furthermore, the high resoluition mass spectrometry showed that the binding ratio of 37 toward G3, G5 and G4 were 1:2, 1:2 and 1:1, respectively. The same method were used to confirm that binding constant and binding ratio of compound 41 toward G5 were 4.37 × 103 M-1 and 1:1. Compound 37 showed binding abilities toward imidazolium cations guest G6-G8, which have different anion Cl-, BF4- and PF6-. Fluorescence intensity of host 37 have best fluorescence enhancement effect when G8 was added, compared with G5-G7. However, there is no significant difference of binding constant between guest G8-G11, which alkyl group have different carbon chain length, toward compound 37. Based on the discussion of binding ability of compound 37 toward G8-G11 and 1H NMR titration, we surmised that guest compounds using cation side to penetrate into the cavity of pillar[5]arene from the side without substituted or bridged group and alkyl chain of guest are outside host cavity. The other part of the study is according to the previous work of laboratory upperclassmen, Yin-Ju Chen. In his study, he reported the synthesis of a pyrazolyl methylpyrene functionalized calix[4]arene 28 and 1,3-alternate calix[4]arene 29 with pyrazolyl methylpyrene on the one end and triazolylphenyl on the other end. These two compound showed good binding ability toward Ag+ and Hg2+, but the binding ratio of compound 28 toward metal ion was ambiguous and compound 29 lack the control compound 58 to comparison. Therefore, we prepared compound 28 and confirmed the binding ratio were 1:1 toward Ag+ and Hg2+ by Job plot and high resoluition mass spectrometry. Besides, we successfully synthesized control compound 58. Based on the results from UV-Vis spectroscopy and fluorescence spectroscopy, same as compound 28, 29, compound 58 showed good binding abilities toward Ag+ and Hg2+, and binding constant were calculated for 3.89 × 107 M-4 and 3.06 × 107 M-4 by Hill equation. Compared with compound 28, 29, binding constant 29·Ag+ > 58·Ag+ > 28·Ag+ and 29·Hg2+ > 58·Hg2+ > 28·Ag2+. This result indicated the propyl group at the upper-rim of control compound 58 would assist to bind metal ion, although it’s not effective as triazole group. According to the binding constant order, Hill plot, Job plot and 1H NMR titration, we surmised that compound 58 have binding ratio 2:3 toward Ag+ and Hg2+.
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Kumari, Archana. "Synthesis of Pyrazolo [3, 4-b] pyridine by Knovengel Condensation." Thesis, 2009. http://ethesis.nitrkl.ac.in/190/1/.
Full textAbstract:
We have successfully prepared some novel pyrazole derivatives. More interestingly, a new pyrazolopyridine derivative i.e. Ethyl 6-amino-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate was prepared by the knovengel condensation of 5-amino-pyrazole-4-carbaldehyde and ethylcyanoacetate.
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Chou, Shih-Yu, and 周世祐. "Calamitic heterocyclic pyrazoles formed by 1,5-bis(4-alkoxyphenyl)-l,3,5-pentanetriones." Thesis, 2008. http://ndltd.ncl.edu.tw/handle/26770058482258289706.
Full textAbstract:
碩士國立中央大學
化學研究所
96
In this thesis, we report the synthesis, characterization and mesomorphic properties of a series of new mesogenic derivatives based on pyrazole structureies. All compounds were characterized by 1H, 13C-NMR spectroscopy and elemental analysis. The phase behaviors of these mesogenic compounds were characterized and studied by differential scanning calorimeter (DSC) and polarization optical microscope. In the serie, a new type of mesogenic compounds derived from heterocyclic pyrazoles were prepared and studied. The compounds of Tpz-Cn, exhibited smectic phases, as expected for their rod-like structures, compounds of Tpz-2Cn, exhibited columnar hexagonal phases, as expected for their discotic-like structures. The metal complexes, Tpz-2Cn-Ni, formed by reacting the pyrazoles with NiCl2 are exhibited columnar hexagonal phases too.
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Lin, Kuan-Ting, and 林冠廷. "Mesogenic Heterocycles Formed by Quinoxalines, Bis–pyrazoles, and Bis–1, 3, 4–Oxadiazoles." Thesis, 2015. http://ndltd.ncl.edu.tw/handle/u7b64v.
Full textAbstract:
碩士國立中央大學
化學學系
103
This thesis is devided into four different series. In series 1, two new structures of unsymmetric 1, 3, 4–oxa(thia)–diazoles 1a–b and 2 containing both quinoxaline and naphthalene moieties were prepared and their mesomorphic properties were investigated. The mesomorphic behavior of compounds 1–2 was studied by DSC analysis and polarized optical microscopy. All compounds 1a and 2 exhibited hexagonal columnar phases (Colh), which were also confirmed by powder XRD diffractometer. Ncell and Rar values equal to 5.23 and 22.73 Å within a slice of 9.0 Å thick were also obtained for 1a (n=16), indicating that a more disc-like structure constructed by two molecules lying side-by-side was correlated in Colh phases. In contrast, all compounds 1b were not mesogenic, and the lack of mesomorphic properties in 1b might be due to their unfavorable conformations. The PL spectra of all compounds 1a, b showed one intense peak at λmax = 509–512 nm, and these photoluminescent emissions originated from quinoxaline moiety. In series 2, four new series of quinoxaline with four kind of 1, 3, 4–oxadiazoles spacer 1a–d were designed and prepared. Their mesomorphic properties were investigated. The mesomorphic behavior of compounds 1a–1d was studied by DSC analysis and polarized optical microscopy. All compounds 1a and 1d exhibited hexagonal columnar phases (Colh), which were also confirmed by powder XRD diffractometer. Ncell values equal to 2.85 and 2.16, Rar values are 20.49 and 22.74 Å within a slice of 9.0 Å thick were also obtained for 1a (n=12) and 1d (n = 12), indicating that a single molecule was packed within the columns in Colh phases. In contrast, all compounds 1c were not mesogenic, and the lack of mesomorphic properties in 1c might be due to their unfavorable conformations. The PL spectra of all compounds 1a–1d showed one intense peak at λmax = 517–529 nm, and these photoluminescent emissions originated from quinoxaline moiety. In series 3, three new materials of catenar liquid crystals 1a–c derived from heterocyclic bisoxazoles and bisthiazoles exhibiting columnar phases were reported. All compounds 1a–c exhibited hexagonal columnar phases, which were also confirmed by powder XRD diffractometer. Compounds 1a have a slightly wider temperature range of columnar phases than those of compounds 1b, which might be attributed to higher core dipole polarized in 1a. A Ncell and Rar value equal to 2.54–2.76 and 19.99–20.45 Å within a slice of 9.0 Å thick were obtained for three derivatives 1a–c (all n = 12), indicating that a single molecule was packed within the columns in Colh phases. All derivatives showed good stabilities at temperature below T = 408.8 C on TGA analysis. The PL spectra of all compounds 1a–c showed one intense peak at λmax = 505–510 nm, and these photoluminescent emissions originated from quinoxaline moiety. In series 4, three new series of multiple heterocyclic compounds 1a–c constructed by bis–pyrazoles, bis–1, 3, 4–oxadiazoles and thiophene exhibiting mesophases were reported. Crystallographic data showed that the crystal 1a (n = 8) is a linear–shaped molecule with a molecular length of ca. 40.57 Å. However, three heterocyclic rings were not coplanar. All compounds 1a formed smectic A/C phases, and all compounds 1c exhibited columnar phases, which were confirmed by powder XRD diffractometer. A Ncell and Rar value equal to 3.91 and 18.29 Å within a slice of 9.0 Å thick were obtained for derivatives 1c (n = 8), indicating that two molecule was correlated within columns in Colh phases. All derivatives showed good stabilities at temperature below T = 383–426 C on TGA. The PL spectra of all compounds 1b–c (n = 8) showed one intense peak at λmax = 418–496 nm, and these photoluminescent emissions originated from 1, 3, 4–oxadiazole moiety.
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Prokofieva, Angelina. "Bioinspired oxidation reactions of phenols with dinuclear copper complexes." Doctoral thesis, 2007. http://hdl.handle.net/11858/00-1735-0000-000D-F12D-0.
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詹淑秦. "Investigation of synthesis and anti-allergic activityof 2-ethyl-3, 4-dimethylfuro [ 2, 3-c ] pyrazoles." Thesis, 1987. http://ndltd.ncl.edu.tw/handle/61087201187943624709.
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Liebold, Claudia. "Immobilisierung von Palladium mittels 1,4-Bis-(4‘-pyrazolyl)benzen und dessen Anwendung in der heterogenen Katalyse: Immobilisierung von Palladium mittels 1,4-Bis-(4‘-pyrazolyl)benzen und dessen Anwendung in der heterogenen Katalyse." Doctoral thesis, 2012. https://tubaf.qucosa.de/id/qucosa%3A22875.
Full textAbstract:
Die Immobilisierung homogener Katalysatoren ist eine wichtige Methode zur Realisierung der Abtrennbarkeit und Wiederverwendbarkeit aktiver Spezies. Im Rahmen dieser Arbeit wurde durch die Komplexierung von Palladium mit 1,4-Bis-(4′-pyrazolyl)benzen ein neues mikroporöses Koordinationspolymer generiert und dieses als heterogener Katalysator in der Suzuki-Miyaura-Kreuzkupplungsreaktion erfolgreich eingesetzt. Dabei konnten vollständige Umsätze und hohe Selektivitäten erzielt werden, die vergleichbar zu bereits kommerziell erhältlichen homogenen Katalysatoren sind. Die Besonderheit des Katalysators ist, neben dessen außergewöhnlich hohen chemischen Stabilität, die Variation seiner Struktureigenschaften durch die Wahl der Synthesebedingungen und die damit verbundene Steuerung seiner katalytischen Aktivität.:1 EINLEITUNG 1
2 KENNTNISSTAND 5
2.1 Immobilisierung von Palladium 5
2.1.1 Organische Trägermaterialien 6
2.1.1.1 Polyanilin 6
2.1.1.2 Polymerverankerte Phosphanliganden 8
2.1.1.3 Imprägnierung komplexfunktionalisierter Polymere 10
2.1.2 Anorganische Trägermaterialien 11
2.1.2.1 Aktivkohle 11
2.1.2.2 Metalloxide 13
2.1.3 Hybridmaterialien 14
2.1.3.1 Infinite Coordination Polymers 14
2.1.3.2 Metal-Organic Frameworks 17
2.2 Die Suzuki-Miyaura-Kreuzkupplungsreaktion 24
2.2.1 Allgemeine mechanistische Vorstellungen zur Reaktion 27
2.2.2 Die PdII/PdIV-Katalyse – Ein umstrittener Mechanismus 29
3 AUFGABENSTELLUNG UND LÖSUNGSSTRATEGIE 33
4 ERGEBNISSE UND DISKUSSION 38
4.1 Charakterisierung des Koordinationspolymers [Pd(BPB)]n 38
4.1.1 Bis(triphenylphosphan)palladium(II)dichlorid als Palladiumprecursor 38
4.1.1.1 Synthese und Charakterisierung 38
4.1.1.2 Porosität 49
4.1.1.3 Oxidationsstufe des Palladium 57
4.1.1.4 Strukturdiskussion 64
4.1.2 Mechanistische Untersuchungen zur Bildung von [Pd(BPB)]n 74
4.1.2.1 Verfolgung des Reaktionsablaufes mittels Kernresonanzspektroskopie 74
4.1.2.2 Vorschläge zum Reaktionsmechanismus 81
4.1.3 Alternative Palladiumprecursoren für [Pd(BPB)]n 88
4.1.3.1 Bis(triphenylphosphan)palladium(II)dibromid 88
4.1.3.2 Natriumtetrachloropalladat 90
4.1.3.3 Weitere Palladiumprecursoren 93
4.1.4 Alternative Synthesetechniken für [Pd(BPB)]n 94
4.1.4.1 Solvothermale Synthese 94
4.1.4.2 Basendiffusionsmethode 95
4.2 Heterogen katalysierte Suzuki-Miyaura-Reaktion mit [Pd(BPB)]n 97
4.2.1 Verifizierung des Versuchsablaufes mittels Vergleichskatalysatoren 97
4.2.2 Die katalytische Aktivität von [Pd(BPB)]n in der Suzuki-Reaktion 100
4.2.3 Katalysatorstabilität und Wiederverwendbarkeit von [Pd(BPB)]n 104
4.2.4 Einfluss der Reaktionstemperatur 110
4.2.5 Einfluss des phosphanhaltigen Palladiumprecursors 114
5 ZUSAMMENFASSUNG 116
A EXPERIMENTELLER TEIL 120
A.1 Synthese und Charakterisierung von [Pd(BPB)]n 120
A.1.1 Arbeitstechniken und verwendete Chemikalien 120
A.1.2 Synthesevorschriften für [Pd(BPB)]n 122
A.1.2.1 Darstellung von 1,4-Bis-(4′-pyrazolyl)benzen (H2BPB) 122
A.1.2.2 Fällungssynthese von [Pd(BPB)]n 122
A.1.2.3 Solvothermale Synthese von [Pd(BPB)]n 123
A.1.2.4 Diffusionskontrollierte Synthese von [Pd(BPB)]n 124
A.1.2.5 Synthese aus Natriumtetrachloropalladat 124
A.1.2.6 Synthese aus Palladiumacetat 124
A.1.2.7 Synthese aus PdBr2(PPh3)2 125
A.1.3 Charakterisierung von [Pd(BPB)]n 125
A.2 Durchführung der Suzuki-Miyaura-Reaktion 127
A.2.1 Umsetzung von 4-Bromacetophenon mit Phenylboronsäure 127
A.2.2 Katalysatorstabilität und Wiederverwendbarkeit 128
A.2.3 Analyse und Identifizierung der Reaktionsprodukte 129
B ANHANG 134
B.1 Charakterisierung von [Pd(BPB)]n 134
B.2 Mechanistische Untersuchungen zur Bildung von [Pd(BPB)]n 140
B.3 Katalytische Aktivität von [Pd(BPB)]n 141
B.4 Tabellenverzeichnis 143
B.5 Abbildungsverzeichnis 145
B.6 Symbole und Abkürzungen 150
B.7 Literaturverzeichnis 154