Relevant bibliographies by topics / Trifluoromethyl compounds

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Academic literature on the topic 'Trifluoromethyl compounds'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Trifluoromethyl compounds"

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Lahsasni, Siham, Dunya A. M. Al-Hemyari, Hazem A. Ghabbour, Yahia Nasser Mabkhoot, Fadilah S. Aleanizy, Asma A. Alothman, and Zainab M. Almarhoon. "Synthesis, Characterization, and Antibacterial and Anti-Inflammatory Activities of New Pyrimidine and Thiophene Derivatives." Journal of Chemistry 2018 (August 1, 2018): 1–11. http://dx.doi.org/10.1155/2018/8536063.

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Substituted[4,5]thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-one (3a–b) and pyrimidin-5(6H)-imine (3c–e) were synthesized via reaction of the starting compounds, ethyl 2-amino-substituted[b]thiophene-3-carboxylate (2a–c) and 2-amino-substituted [b]thiophene-3-carbonitrile (2d–f), respectively, with 2-bromothiazole. Synthesis of (bromo-substituted[b]thiophen-2-yl)alkanamide derivatives (4a–e) and thieno[2,3-d][1,3]oxazin-4-imine derivative (5) was accomplished via reaction of the starting compounds with bromoalkyl chloride through nucleophilic substitution; however, for the synthesis of compound 5, nucleophilic substitution was followed by nucleophilic addition to a nitrile group to form the oxazinimine ring. 1-(3-cyano-substituted[b]thiophen-2-yl)-3-(4-(trifluoromethyl)phenyl)thiourea derivatives (6a–c) were obtained via reaction of the starting compounds (2d–f) and 4-(trifluoromethyl phenyl)isothiocyanate. The lead compounds (2d–f) rapidly reacted with 4-(trifluoromethyl)benzaldehyde or 4-(2-pyridyl)benzaldehyde in acidic medium to yield compounds (7a–f) in large quantities. X-ray crystallography of compounds 4c and 7e confirmed their structures. Antimicrobial studies revealed that compound 6a was equally potent to ampicillin against Bacillus strains. Moreover, compounds 3e, 4d, and 6a possessed greater anti-inflammatory potency than that of the standard drug.
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Zouaoui, Emna, and Mohamed Moncef El Gaïed. "Synthesis of Trifluoromethyl Heterocyclic Compounds." Journal of Chemical Research 2003, no. 4 (April 2003): 242–46. http://dx.doi.org/10.1177/1747519803200300404.

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Hafez, Hend N., and Abdel-Rahman B. A. El-Gazzar. "Synthesis of Novel Pyridine Bearing Biologically Active Imidiazolyl, Pyrazolyl, Oxa/thiadiazolyl and Urea Derivatives as Promising Anticancer Agents." Current Organic Synthesis 17, no. 1 (February 24, 2020): 55–64. http://dx.doi.org/10.2174/1570179417666191223163225.

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Background: A novel series of pyridine containing 1,3,4-oxa/thiadiazol derivatives 4a,b, pyrazole derivatives 5-7, thiazole derivatives 9a,b and 17a-c, urea derivatives 12a-c, imidiazole derivative 16, imidazo[1,2-a]pyridine derivatives 18a, b, tetrazole 19, pyrane 20 and pyridine derivatives 21 has been synthesized. Objective: This research aims to synthesize 6-(Trifluoromethyl)-2-[3-(trifluoromethyl)phenyl] amino nicotinohydrazide 2 and 6-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino pyridin-3-carboaldhyde 15 as key intermediate for the synthesis of novel pyridine derivatives bearing different heterocyclic rings in order to study the additive effect of this ring toward tumor cell lines. Methods: 6-(Trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino nicotinohydrazide 2 was synthesized in a series of synthetic steps and was used as key intermediate for the synthesis of compounds 3-(1,3,4- oxa/thiadiazol-2-yl)-6-(trifluoromethyl)-N-(3- trifluoromethyl) phenyl) pyridin-2-amine 4a,b, (3,5-dimethyl- 1H-pyrazol-1-yl derivatives) [6-(trifluoromethyl)-2-[3- trifluoromethyl) phenyl] amino pyridin-3- yl]methanone 5a,b, 6-8, 9a,b and 12a-c. Also, 6-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]amino pyridin-3-carboaldhyde (15) was used as a key intermediate for the synthesis of novel series of pyridine derivatives with different heterocyclic ring (16-21). Results: Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All the synthesized compounds were screened for their in vitro anticancer activity against liver cancer (HepG2), human colon cancer (HT-29) and human breast adenocarcinoma cell lines (MCF-7). Conclusion: All the synthesized compounds were investigated for their in vitro antitumor activity. Compounds 4b, 9a,b and 19 showed higher antitumor activity than the doxorubicin. Interestingly, pyridine with pfluorophenyl urea 12a demonstrated the most potent antitumor activity. The activity of these compounds is strongly dependent on the basic skeleton of the molecules and the nature of the heterocyclic ring attached to the pyridine moiety.
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Zouaoui, Emna, and Mohamed Moncef El Gaïed. "Synthesis of trifluoromethyl heterocyclic compounds." Journal of Chemical Research 2003, no. 4 (April 1, 2003): 242–46. http://dx.doi.org/10.3184/030823403103173651.

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Mandadi, Manoj Kumar, Ramana Reddy Bobbala, Balakrishna Kolli, and Rambabu Gundla. "Synthesis and Anticancer Activity of Novel Amide Tagged Trifluoromethyl Indole and Pyrimido Indole Derivatives." Asian Journal of Chemistry 33, no. 10 (2021): 2327–32. http://dx.doi.org/10.14233/ajchem.2021.23313.

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A series of novel amide tagged trifluoromethyl indole and pyrimido indole derivatives 4a-e & 5a-e and 6a-d & 7a-d were synthesized from 4-methyl-2-(methylamino)-6-(trifluoromethyl)isophthalonitrile (1) on reaction with bromoethyl acetate to obtain 2a and 2b isomers. Compound 2a treated with hydrazine hydrate followed by Schiff base reaction to get compounds 4a-e. In another way, compound 2a on reaction with aliphatic primary amine to get compounds 6a-d. For cyclization, compounds 4a-e & 6a-d treated with trifluoroacetic acid to obtain compounds 5a-e and 7a-d, respectively. All the synthesized compounds 4a-e & 5a-e and 6a-d & 7a-d were tested for anticancer activity against four human cancer cell lines such as A549-lung cancer (CCL-185), MCF7-breast cancer (HTB-22), DU145-prostate cancer (HTB-81) and HeLa-cervical cancer (CCL-2). Compounds 9e and 9f were found to have promising anticancer activity at micromolar concentration.
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Suchetan, P. A., E. Suresha, S. Naveen, and N. K. Lokanath. "Crystal structures of 3-fluoro-N-[2-(trifluoromethyl)phenyl]benzamide, 3-bromo-N-[2-(trifluoromethyl)phenyl]benzamide and 3-iodo-N-[2-(trifluoromethyl)phenyl]benzamide." Acta Crystallographica Section E Crystallographic Communications 72, no. 6 (May 17, 2016): 819–23. http://dx.doi.org/10.1107/s2056989016007866.

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In the title compounds, C14H9F4NO, (I), C14H9BrF3NO, (II), and C14H9F3INO, (III), the two benzene rings are inclined to one another by 43.94 (8)° in moleculeAand 55.66 (7)° in moleculeBof compound (I), which crystallizes with two independent molecules in the asymmetric unit, but by only 10.40 (12)° in compound (II) and 12.5 (2)° in compound (III). In the crystals of all three compounds, N—H...O hydrogen bonds link the molecules to form chains propagating along thea-axis direction for (I), and along theb-axis direction for (II) and (III). In the crystal of (I), –A–B–A–B– chains are linked by C—H...O hydrogen bonds, forming layers parallel to (010). Within the layers there are weak offset π–π interactions present [intercentroid distances = 3.868 (1) and 3.855 (1) Å]. In the crystals of (II) and (III), the chains are linkedviashort halogen–halogen contacts [Br...Br = 3.6141 (4) Å in (II) and I...I = 3.7797 (5) Å in (III)], resulting in the formation of ribbons propagating along theb-axis direction.
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Gajdoš, Peter, Soňa Pavlíková, Filip Bureš, and Alžbeta Krutošíková. "2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions." Open Chemistry 3, no. 2 (June 1, 2005): 311–25. http://dx.doi.org/10.2478/bf02475999.

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AbstractThe synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described. Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N-substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. By heating 2-[3-(trifluoromethyl)phenly]-4H-furo[3,2-b]pyrrole-5-carboxylic acid (2a) in acetic anhydride, 4-acetyl-2-[3-(trifluoromethyl)phenyl]furo[3,2-b]pyrrole (4) was formed. By hydrolysis of 4, 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole (5a) was formed, and reactions with methyl iodide or benzyl chloride gave N-substituted products 5b-c. The reaction of 4 with dimethyl butynedioate gave substituted benzo[b]furan 6. Compound 3a reacted with triethyl orthoesters giving 7a-c, which afforded with phosphorus (V) sulphide the corresponding thiones 8a-c. The thiones 8a-c reacted with hydrazine hydrate to form hydrazine derivatives 9a-c. The reaction of triethyl orthoformiate with compounds 9a-c led to furo[2′,3′: 4,5]pyrrolo[1,2-d][1,2,4]triazolo[3,4-f][1,2,4]triazines 10a-c. Hydrazones 11a-c were formed from 3a-c and 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with “classical” conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.
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Liang, Yumeng, Akihito Taya, Zhengyu Zhao, Norimichi Saito, and Norio Shibata. "Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions." Beilstein Journal of Organic Chemistry 16 (December 14, 2020): 3052–58. http://dx.doi.org/10.3762/bjoc.16.254.

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A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD® and Olah’s reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.
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Betala, Sailu, Hanumandlu Racha, and Chiranjeevi Abba. "Synthesis of Novel Triazolothione, Thiadiazole, Triazole and Oxadiazole Functionalized Tri-fluoromethylnaphthyridine Derivatives and their Anticancer Activity & Antimicrobial Activity." Asian Journal of Chemistry 32, no. 8 (2020): 1931–40. http://dx.doi.org/10.14233/ajchem.2020.22688.

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Novel triazolothione, thiadiazole, triazole and oxadiazole-tagged trifluoromethyl group containing naphthyridine derivatives (6a-l and 7a-d) were synthesized from 2-amino-6-(thiophen-2-yl)-4- (trifluoromethyl)nicotinonitrile (1) on treatment with acetophenone and obtained 2-phenyl-7-(thiophen- 2-yl)-5-(trifluoromethyl)-1,8-naphthyridin-4-amine (2), compound 2 on reaction with bromoethylacetate and after that reaction with hydrazine hydrate and obtained carbohydrazide derivatives (4), compound 4 on reaction with different substituted phenyl isothiocyanates to obtain phenyl hydrazine carbothiamide derivatives (5). Compound 5 is independently reaction with NaOH, H2SO4 and N2H4·H2O to obtain triazolothione, thiadiazole, triazole-substituted naphthyridine derivatives (6a-l), respectively. The carbohydrazide compounds 4 on reaction with diverse substituted aromatic acids and obtained oxadiazole derivatives (7a-d). All the synthesized compounds (6a-l and 7a-d) were tested for anticancer activity against four cancer cell lines such as “HeLa-cervical cancer (CCL-2) COLO 205-colon cancer (CCL-222) HepG2-liver cancer (HB-8065) MCF7-breast cancer (HTB-22) and one normal cell line (HEK 293)”. Compounds 6b, 6d and 6l are known to have good anticancer activity at micro molar concentration and found to be non-toxic on normal cell line. And all the products 6a-o and 7a-d were tested against Gram-positive, Gram-negative bacteria and fungal strains. All the compounds, compounds 6e-h showed more activity against Bacillus subtilis (MTCC-121) at < 6.8 micromolar concentration. Compounds (which showed more activity) further screened for minimum bactericidal concentration against B. subtilis MTCC 121 using ciprofloxacin as standard and known to show optimistic activity. These compounds further tested for biofilm inhibition activity against B. subtilis MTCC 121 using erythromycin as standard which confirmed the high activity.
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Beara, Ivana, Tatjana Majkić, Stefania Fioravanti, Laura Trulli, Neda Mimica-Dukić, Lucio Pellacani, and Luciano Saso. "The Effects of Trifluoromethylated Derivatives on Prostaglandin E2 and Thromboxane A2 Production in Human Leukemic U937 Macrophages." Medicinal Chemistry 16, no. 1 (January 16, 2020): 63–68. http://dx.doi.org/10.2174/1573406415666190208150253.

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Background: A convenient approach to modulation of the inflammation has an influence on the production of inflammatory mediators – icosanoids, generated in arachidonic acid (AA) metabolism. The common therapeutic activity of non-steroidal anti-inflammatory drugs (NSAID), such as aspirin, includes inhibition of two crucial enzymes of AA metabolism - cyclooxygenase- 1 and -2 (COX-1/2), with certain risk for gastrointestinal and renal intolerance. Ever since the enrolment of COX-2, particularly overabundance of its main products prostaglandin E2 (PGE2) and thromboxane A2 (TXA2) in numerous pathological processes was recognized, it became a significant therapeutic target. Objective: The aim of this study was to examine the effects of synthesized organo-fluorine compounds on PGE2 and TXA2 production in the inflammation process. Methods: Trifluoromethyl compounds were synthesized from N-benzyl trifluoromethyl aldimine, commercially available 2-methyl or 2-phenyl α-bromo esters (β-lactams trans-1 and trans-2 and trifluoromethyl β-amino ester, respectively) and methyl 2-isocyanoacetate (2-imidazoline trans-4). The reactions proceeded with high geometric selectivity, furnishing the desired products in good yields. The influence of newly synthesized compounds on PGE2 and TXA2 production in human leukemic U937 macrophages on both enzyme activity and gene expression levels was observed. Results: Among the tested trifluoromethyl compounds, methyl trans-1-benzyl-5-(trifluoromethyl)- 4,5-dihydro-1H-imidazole-4-carboxylate (trans-4) can be distinguished as the most powerful antiinflammatory agent, probably due to its trifluoromethyl-imidazoline moiety. Conclusion: Some further structural modifications in tested compounds and particularly in the synthesis of different trifluoromethyl imidazolines could contribute to the development of new COX-2 inhibitors and potent anti-inflammatory agents.
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Dissertations / Theses on the topic "Trifluoromethyl compounds"

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Kucheryna, Andriy. "Syntheses and properties of compounds containing the bis(trifluoromethyl)amido group." [S.l.] : [s.n.], 2006. http://deposit.ddb.de/cgi-bin/dokserv?idn=983674019.

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Wang, Jian. "Heteroaryl(trifluoromethyl)carbenes and related strained cumulenes under matrix isolation conditions." abstract and full text PDF (free order & download UNR users only), 2007. http://0-gateway.proquest.com.innopac.library.unr.edu/openurl?url_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:dissertation&res_dat=xri:pqdiss&rft_dat=xri:pqdiss:3289461.

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Sequeira, L. J. "Studies on main group and transition metal compounds containing a sterically demanding, electron-withdrawing ligand." Thesis, Durham University, 1996. http://etheses.dur.ac.uk/5396/.

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The studies described herein relate to the co-ordination chemistry of l,3,5-tris(trifluoromethyl)benzene, Ar(^F)H. The unique combination of steric bulk and a highly electron-withdrawing nature found in the a- bound Ar(^F) ligand has already been exploited to stabilise a variety of unusual main group compounds including the surprisingly air- and moisture-stable diphosphene Ar(^F)P=Par(^F). Other examples are discussed in the introductory chapter, as is the increasingly active area of diphosphene research. Chapter 2 describes the synthesis and structural characterisation of six early σ-Ar(^F) transition metal complexes, Mo(N(^t)Bu)(_2)(Ar(^F))2, Cr(NAd)(_2)(Ar(^F))(_2), [Mo(NAr)(_2)(Ar(^F))Cl-LiCl(dme)](_2), V(Ar(^F))(_2)Cl(thf), V(Ar(^F))(_3)-O -Li(thf)(_3) and Cr(Ar(^F))(_2)(PMe(_3))(_2). The first five of these compounds exhibit the rare phenomenon of weak metal-fluorine interactions, which is discussed in terms of several structural factors such as tilting of the aryl ring towards the direction of the M-F interaction The co-ordination chemistry of the diphosphenes Ar(^F)p=PArF, Ar*P=PAr* and Ar*P=PArF (Ar* = 2,4,6-(^t)BuC6H3) is reported in chapter 3. Ar(^F)p=Par(^F) is shown to displace olefins from a bis(imido)molybdenum centre to generate complexes such as Mo(NR)(_2)(PMe)(_3)(Ti2-ArFp=PArF) (R = tBu, 2,6-iPr2C6H3). The crystal structure of Mo(NtBu)2(PMe)3(Ti2- ArFp=PArF) has been elucidated. Related investigations have focused on the co-ordination mode of the diphosphenes Ar*P=PAr* and Ar*P=PArFwith [Pt(PEt3)Cl2]2/ and a variety of Til-complexes has been spectroscopically observed. The development of phosphorus based analogue of the industrially important olefin metathesis reaction is detailed in chapter 4. The reaction of ArPCl2, [Ar = Ar(^F), Ar* and 2,6-(CF3)2-C6H3 (Ar(^f1)] with the halide abstractor W(PMe3)6 leads to the generation of ArP=PAr via a postulated [W]=PAr phosphinidene intermediate. The unsymmetrical diphosphene ArFp=PAr* has been synthesised analogously from a mixture of ArFPCl2 and Ar*PCl2 with W(PMe3)6- When Ar is small (2,4,6-iPr3C6H2, 2,4,6- Me3C6H2), ArPCl2 reacts with W(PMe3)6 to give three-membered tricyclophosphanes, [ArP](_3) π-bound complexes of the Ar(^F)H ligand have been synthesised via metal vapour synthesis experiments, carried out in collaboration with Prof. F.G.N. Cloke at Sussex University. Chapter 5 describes the preparation of the bis-arene complexes M(T|6-ArFH)2 (M=Cr, V, Nb) and Ru(Ti6-ArFH)(Ti4-ArFH).Full experimental details and characterising data for chapters 2-5 are collected in chapter 6.
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Rezai, M. Reza. "Synthesis of some biologically important compounds containing the bis(trifluoromethyl)ketal group as phosphate mimics." Thesis, Brunel University, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.311540.

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Chang, Liang. "Sustainable Transformations of Methyl Coumalate : efficient Preparations of Unsaturated Carboxylic Acids, 2HPyrans, Trifluoromethyl Benzenes and Fluorescents Molecules." Thesis, Sorbonne université, 2018. http://www.theses.fr/2018SORUS109.

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Dans ce travail, nous décrivons le développement de nouvelles transformations utilisant le coumalate de méthyle, composé renouvelable biosourcé. Un couplage double séquentiel d'alkyl-alkyle ou d'alkyl-hydrure one-pot conduit à des acides insaturés d’intérêt. Nous décrivons une synthèse efficace de 2H-pyranes tétrasubstitués dans des conditions douces, puis nous décrivons une réaction efficace et sans solvant avec des dicétones trifluorométhylées, pour conduire à des benzènes trifluorométhylés. Enfin, nous avons rapporté une nouvelle stratégie générale de réaction de désaromatisation de composés hétérocycliques de type pyrido [1, 2-a] bicycliques
In this work, we have described the development of new transformations using bio-based renewable methyl coumalate as feedstock. An iron and copper catalyzed one-pot sequential double alkyl-alkyl or alkyl-hydride 1,6-addition with methyl coumalate was described. We then described an efficient synthesis of tetrasubstituted 2H-pyrans under mild condition. Later we reported a solvent-free reaction of methyl coumalate with trifluoromethyl-β-diketones, in a tBuOK-catalyzed domino sequence. A novel reaction, for efficient C-C bond formation between the bio-based methyl coumalate and a variety of imines and aldehydes via MBH pathway was reported. Finally, we reported a novel, general dearomatization strategy with an unprecedented pyrido[1, 2-a] fused heterocyclic scope
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Aiguabella, Font Nuria. "Reactivity and Applications of New Substrates for the Intermolecular Pauson-Khand Reaction: N-Boc-propargylamines and trifluoromethyl alkynes." Doctoral thesis, Universitat de Barcelona, 2014. http://hdl.handle.net/10803/131864.

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The Pauson-Khand reaction (PKR) is, formally, a [2+2+1] cycloaddition involving an alkene, an alkyne and a carbon monoxide molecule, typically mediated or catalyzed by a cobalt (0) complex. The product of this reaction is a cyclopentenone. This reaction, discovered in 1973 by P. L. Pauson and I. U. Khand constitutes, nowadays, one of the most prominent methods for the synthesis of five-membered ring compounds. Regarding whether the alkene and the alkyne belong to the same molecule or are two different entities, we refer to the intra or intermolecular PKR, respectively. The intramolecular PKR has been the most extensively used one, since it allows the formation of complex polycyclic structures in very few synthetic steps and both the regio and stereoselectivity of the reaction are substrate-controlled. The intermolecular PKR has been traditionally less studied and exploited due to the limitations it presents. First of all, when the alkyne is internal and non-symmetrical the reaction may yield mixtures of regioisomers in different proportions depending on the electronic and steric properties of the substituents. If the reaction is carried out with a terminal alkyne, only one product is formed: the one that has the substituent alpha to the carbonyl in the final cyclopentenone. On the other hand, the reaction is very tolerant to different alkynes, but only tensioned and cyclic alkenes react satisfactorily, ethylene being an exception to this rule. Cyclopentanic compounds are very abundant in nature, and they present a great variety of structures and functions. Probably, two of the most well-known families of cyclopentanic compounds in nature are prostaglandins and phytoprostanes. Prostaglandins are generated by the action of cyclooxygenase (COX) on the fatty acids that come from the phospholipid bilayer. The most common substrate for this reaction cascade in the human body is arachidonic acid. In plants, a similar process occurs with linolenic acid as substrate and the family of phytoprostanes as product. The extremely interesting properties of these compounds, such as antitumor activity, along with the difficulty to isolate them from natural sources, has led to an increasing interest on finding simple and efficient methods to access them. The fact that these products share a cyclopentenone ring (or a derivative) as a structural feature makes them aperfect synthetic target for the PKR. During the present thesis, we have developed a methodology to synthesize prostaglandins and phytoprostanes from the PK adduct of norbornadiene and N-Bocpropargylamine. The synthesis of the aforementioned starting material can be carried out enantioselectively, so that the synthetic target can also be obtained as a single enantiomer. This methodology has been applied to the synthesis of a natural phytoprostane derivative: the methyl ester of 13-epi-12-oxo Phytodienoic acid. The introduction of fluorinated substituents in organic molecules is extremely interesting, since the presence of these functional groups modifies the chemical and physical properties of the molecules to which they are incorporated. Given that, at the beginning of this thesis, there were no precedents of the intermolecular PKR of fluorinated alkynes, and considering that the particular stereoelectronic properties of these products could have an interesting impact on the regiochemical outcome of the PKR, we decided to study them in this work. Our main conclusion has been that fluorinated substituents always occupy the alpha position to the carbonyl in the final cyclopentenone. This fact indicates that the steric bulk of fluorinated groups is larger than expected and overcomes its electronic properties (it is accepted that electron-donating groups prefer the alpha position in the final PK adduct, whereas electron-withdrawing groups prefer the beta position). Furthermore, in the case of trifluoromethyl alkynes, we have developed a methodology that allows to remove this group in order to obtain the previously unknown beta-substituted regiosiomers of PK adducts of terminal alkynes. We have also developed a methodology to carry out the synthesis of trifluoromethyl PK adducts enantioselectively. As an application of our methodology, we have developed a formal synthesis of alpha-cuparenone, a naturally occurring sesquiterpene.
La reacción de Pauson-Khand (PKR) es, formalmente, una cicloadición [2+2+1] que transcurre entre un alqueno, un alquino y una molécula de monóxido de carbono. Como producto de esta reacción, típicamente mediada o catalizada por un complejo de cobalto (0), se genera una ciclopentenona. Los compuestos ciclopentánicos son muy abundantes en la naturaleza, y presentan gran variedad estructural y funcional. Probablemente, dos de las familias de compuestos ciclopentánicos más conocidas son la de las prostaglandinas y la de los fitoprostanos. En los últimos años se ha descubierto que algunos de estos productos (o derivados) poseen propiedades altamente interesantes (como, por ejemplo, actividad antitumoral). La dificultad de aislarlos de fuentes naturales ha despertado un gran interés por desarrollar métodos eficientes para obtenerlos sintéticamente. Dado que estos productos comparten un anillo de ciclopentenona como elemento estructural, constituyen unos substratos ideales para ser sintetizados mediante una PKR. Durante la presente tesis se ha desarrollado una metodología para sintetizar prostaglandinas y fitoprostanos a partir del aducto de PK del norbornadieno y la N-Bocpropargilamina. La síntesis de dicho producto de partida puede realizarse de manera enantioselectiva, de modo que el producto final puede obtenerse, asimismo, de modo ópticamente enriquecido. Esta metodología se ha ensayado con la síntesis del éster metílico de un fitoprostano natural: el ácido 13-epi-12-oxo fitodienóico. Por otro lado, al inicio de esta tesis, no se había realizado nunca una PKR intermolecular con alquinos fluorados y considerando que las particulares propiedades esteroelectrónicas de estos productos podían influir de un modo interesante en la regioquímica de la reacción, decidimos estudiarlos en profundidad durante esta tesis. La principal conclusión que se ha obtenido es que los substituyentes fluorados siempre ocupan la posición alfa al carbonilo en las ciclopentenonas finales. En el caso de que el substituyente fluorado sea un trifluorometilo, se ha desarrollado una metodología que permite quitarlo para obtener los hasta ahora desconocidos regioisómeros de aductos de PK de alquinos terminales. También se ha desarrollado una metodología para realizar dichas PKRs de forma asimétrica y obtener los aductos ópticamente puros. Como aplicación de esta estrategia, se ha realizado una síntesis formal de la alfa-cuparenona, un sesquiterpeno natural.
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7

Garcia, Fábio Dutra. "Novos Espirocromenil-Trifluoretanonas a partir de Reações de Trifluoracetilação de Adutos de Kabbe e seus Espiro[diidrocromeno-cicloalcan]pirazóis e Isoxazóis Derivados." Universidade Federal de Santa Maria, 2013. http://repositorio.ufsm.br/handle/1/10564.

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This work describes firstly an efficient and regioselective method for the synthesis of a new series of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1 -cycloalkan)-3-yl]ethanones from the Kabbe adducts (spiro[chroman-2,1 -cycloalkan]-4-ones). Yields of 38 % to 61 % were obtained when trifluoroacetylation reactions of mixtures of enolethers and/or acetals derived from four spiro ketones (Kabbe adducts) were performed at a temperature of 45 oC and employing anhydrous chloroform as the solvent. Subsequently, when the respective trifluoroacetylated Kabbe adducts reacted with phenylhydrazine and methylhydrazine at a 1:1 molar ratio in refluxing ethanol for 24 hours, a new series of seven examples of a novel spiro-condensed heterocyclic system, namely 1(2)-methyl(phenyl)-3-(trifluoromethyl)-1,4(2,4)-dihydro-spiro(chromen[4,3-c]pyrazole-4,n -cycloalkanes) where cycloalkanes are cyclopentane, cyclohexane and cycloheptane (n = 1) and tetrahydro-2H-pyran (n = 2) were isolated at yields of between 35 % and 51 %. NMR and X-ray diffraction techniques demonstrated clearly that reactions from methylhydrazine and phenylhydrazine were regioselective and allowed to isolate separately the 1,3- and 2,3-trifluoromethylated isomers, respectively. Subsequently, two examples of new 3-hydroxy-3-(trifluoromethyl)-3,3a-dihydro-4H-spiro(chromen[4,3-c]isoxazole-4,1 -cycloalkanes), derivated from cyclopentanone and cyclopentanone, were obtained from the reaction of 2,2,2-trifluoro-1-[4-methoxy-spiro(2H-chromen-2,1 -cycloalkan)-3-yl]ethanones with hydroxylamine hydrochloride in yields of 42% and 58%, respectively. Finally, the structures of new spiro heterocycles were determined with the aid and simultaneous application of 1H-, 13C{1H}- and 19F-NMR, X-ray monocrystal diffraction, Mass Spectrometry and DFT calculation techniques and their purity were proved by elemental analysis or High Resolution Mass Spectrometry (HRMS).
O presente trabalho descreve inicialmente um método eficiente e regiosseletivo para a síntese de uma nova série de 2,2,2-triflúor-1-[4-metóxi-espiro(2H-cromen-2,1 -cicloalcan)-3-il]etanonas a partir de adutos de Kabbe (espiro[croman-2,1 -cicloalcan]-4-onas). Rendimentos de 38% a 61% foram obtidos quando reações de trifluoracetilação de misturas de enoléteres e/ou acetais derivados de quatro espiro cetonas (adutos de Kabbe) foram realizadas a 45 ºC usando clorofórmio anidro como solvente. Subsequentemente, quando os respectivos adutos de Kabbe trifluoracetilados foram reagidos com fenilhidrazina ou metilhidrazina, em relação molar de 1:1, sob refluxo de etanol por 24 horas, uma série de sete exemplares de um novo sistema heterocíclico espiro-condensado, denominado 1(2)-metil(fenil)-3-(trifluormetil)-1,4(2,4)-diidro-espiro(chromen[4,3-c]pirazol-4,n -cicloalcanos) onde os cicloalcanos são ciclopentano, ciclohexano e cicloheptano (n = 1) e tetraidro-2H-pirano (n = 2), foi isolada em rendimentos entre 35 % e 51 %. Técnicas de RMN e de difração de raios-X demonstraram claramente que as reações a partir da metilhidrazina e da fenilhidrazina foram regiosseletivas e permitiram isolar separadamente os isômeros trifluormetilados 1,3 e 2,3, respectivamente. Em sequência, dois exemplares de novas 3-hidróxi-3-(trifluormetil)-3,3a-diidro-4H-espiro(cromen[4,3-c]isoxazol-4,1 -cicloalcanos), derivados da ciclopentanona e ciclohexanona, foram obtidos a partir da reação de 2,2,2-triflúor-1-[4-metóxi-espiro(2H-cromen-2,1 -cicloalcan)-3-il]etanonas com cloridrato de hidroxilamina em rendimentos de 42% e 58%, respectivamente. Finalmente, as estruturas dos novos espiro heterociclos foram determinadas com o auxílio e aplicação simultânea de experimentos de RMN de 1H, 13C{1H}, 19F, difração de raios-X em monocristais, Espectrometria de Massas e cálculos DFT e, a sua pureza comprovada por Análise Elementar ou por Espectrometria de Massas de Alta Resolução (HRMS).
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8

Huang, Weisheng. "Catalytic asymmetric cyclopropanation and oxidation of tri-, di- and monofluoromethyl styrenes Rhodium catalysed enantioselective synthesis of mono-(halo)-methyl-cyclopropanes Catalytic enantioselective synthesis of highly functionalized difluoromethylated cyclopropanes General catalytic enantioselective access to monohalomethyl and trifluoromethyl cyclopropanes Catalytic asymmetric synthesis of α,α-difluoromethylated and α-fluoromethylated tertiary alcohols." Thesis, Normandie, 2019. http://www.theses.fr/2019NORMIR25.

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Ce manuscrit décrit la synthèse énantiosélective de cyclopropanes trifluorométhylés, difluorométhylés et mono-halométhylés hautement fonctionnalisés. Cette synthèse repose sur la cyclopropanation d’alcènes. De plus, la synthèse d’alcools tertiaires difluorométhylés à partir des oléfines fluorées correspondantes suivant un processus de dihydroxylation asymétrique est décrite. Ce manuscrit se découpe en 3 chapitres. Le premier chapitre décrit la première synthèse catalytique asymétrique de cyclopropanes difluorométhylés en utilisant le Rh₂((S)-BTPCP)₄ comme catalyseur pour la réaction de cyclopropanation d’oléfines α,α-difluoromethylées avec des composés diazoïques di-accepteurs. Un large éventail de cyclopropanes a été obtenu avec de très bon rendements et d’excellentes diastéréosélectivités et énantiosélectivités (>20:1 et jusqu’à 99% ee). Le second chapitre illustre la synthèse de cyclopropanes trifluorométhylés suivant une stratégie similaire. Ces derniers ont été obtenus avec des très bons rendements et d’excellentes diastéréosélectivités et énantiosélectivités (>20:1 et jusqu’à 99% ee). Ces travaux ont également permis une extension aux dérivés mono-halométhylés. Dans un troisième chapitre, l’époxydation asymétrique de styrenes α,α-difluoromethylés a été étudiée. Malheureusement, tous les essais métallo- ou organocatalysés se sont avérés infructueux. Par la suite la réaction de dihydroxylation asymétrique de ces styrenes α,α-difluorométhylés a été développée pour conduire aux alcools tertiaires difluorométhylés énantioenrichis. L’utilisation d’AD-mix-α et AD-mix-β comme catalyseurs a permis d’obtenir les produits désirés avec de très bons rendements et d’excellentes énantiosélectivités. De plus, cette réaction a été étendue aux styrenes α,α-difluorométhylés, α-monofluorométhylés, β-difluoromethylé et β-trifluorométhylé
This thesis presents the enantioselective synthesis of functionalized trifluoromethyl, difluoromethyl and monohalomethyl cyclopropanes based on the cyclopropanation reaction of alkenes bearing various fluorinated groups. In addition, the synthesis of enantioenriched fluorinated tertiary alcohols resulting from the dihydroxylation of fluorinated olefins is discussed. This thesis is divided into three chapters. In the first chapter, we reported the first example of catalytic asymmetric synthesis of difluoromethyl cyclopropanes, which is achieved by using Rh₂((S)-BTPCP)₄ as a catalyst to perform the cyclopropanation reaction of α,α-difluoromethyl olefins with donor-acceptor diazo compounds and di-acceptor diazo compounds. This methodology allows the access to a broad range of cyclopropanes in high yields with excellent diastereo- and enantioselectivities (up to >20:1 and up to 99% ee). In the second chapter, a practical and efficient asymmetric synthesis of trifluoromethyl cyclopropane derivatives was described and a series of functionalized cyclopropanes were obtained in excellent diastereoselectivities with excellent enantioselectivities (up to >20:1 and 99% ee). These investigations also extended to the synthesis of highly enantioselective monohalomethyl cyclopropanes. In the third chapter, the initial propose aimed at exploring the asymmetric epoxidation of α,α-difluoromethyl styrenes. The reaction was performed in the presence of a metal-catalyst or an organic catalyst, unfortunately, none of the result was positive. Therefore, we turned our attention to the asymmetric synthesis of α,α difluoromethylated tertiary alcohols. To this propose, the use of commercially available reagents AD-mix-α and AD-mix-β as the best catalysts, allowed the reaction with α,α-difluoromethyl styrenes to construct the corresponding α,α-difluoromethylated tertiary alcohols in good to high yields with excellent enantioselectivities (up to 99% ee). In addition, this transformation could be applied to a broad range of substrates, including variety of α,α-difluoromethyl styrenes, α-monofluoromethyl styrenes, β-difluoromethyl styrene and β-trifluoromethyl styrene
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9

Francese, Catherine. "Reactions du bromotrifluoromethane en presence de zinc : trifluoromethylations dans les conditions de barbier." Paris 6, 1987. http://www.theses.fr/1987PA066381.

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Kucheryna, Andriy [Verfasser]. "Syntheses and properties of compounds containing the bis(trifluoromethyl)amido group / von Andriy Kucheryna." 2006. http://d-nb.info/983674019/34.

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Books on the topic "Trifluoromethyl compounds"

1

Nenajdenko, Valentine G. Chemistry of [alpha], [beta]-unsaturated trifluoromethly [i.e. trifluoromethyl] ketones. New York: Nova Science Publishers, Inc., 2007.

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Banger, K. K. Synthesis, structure and reactivity of inorganic perfluorovinyl and trifluoromethyl compounds. Manchester: UMIST, 1998.

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3

Center, Langley Research, ed. Trifluoromethyl-substituted polymers: Semiannual status report, January 1, 1990 to June 30, 1990. San Marcos, TX: Dept. of Chemistry, Southwest Texas State University, 1990.

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Center, Langley Research, ed. Trifluoromethyl-substituted polymers: Semiannual status report, January 1, 1990 to June 30, 1990. San Marcos, TX: Dept. of Chemistry, Southwest Texas State University, 1990.

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5

D, Bills T., Gilderhus P. A, and Johnson D. A, eds. Effects of the lampricide 3-trifluoromethyl-4-nitrophenol on the pink heelsplitter. Washington, D.C: U.S. Dept. of the Interior, Fish and Wildlife Service, 1992.

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Book chapters on the topic "Trifluoromethyl compounds"

1

Burton, Donald J., and Donald A. Wiebe. "Preparation of 2-Trifluoromethyl-3,3,3-trifluoropropanal." In Efficient Preparations of Fluorine Compounds, 250–51. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2012. http://dx.doi.org/10.1002/9781118409466.ch40.

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Shreeve, Jean'ne M. "Trifluoromethyl Compounds via Electrophilic and Nucleophilic Reactions." In Efficient Preparations of Fluorine Compounds, 121–26. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2012. http://dx.doi.org/10.1002/9781118409466.ch21.

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Umemoto, Teruo. "Preparation of Power-Variable Electrophilic Trifluoromethylating Agents,S-(Trifluoromethyl)dibenzothiophenium Salts Series." In Efficient Preparations of Fluorine Compounds, 279–89. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2012. http://dx.doi.org/10.1002/9781118409466.ch47.

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Tyrra, Wieland, and Silke Kremer. "Synthesis of Zero-Valent Trifluoromethyl Chalcogenato Derivatives, [NMe4]ECF3(E = S, Se, Te), and Related Compounds." In Efficient Preparations of Fluorine Compounds, 26–34. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2012. http://dx.doi.org/10.1002/9781118409466.ch8.

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Abu Ali, H., V. M. Dembitsky, and M. Srebnik. "Ozonolysis of (Trifluoromethyl)(trifluorovinyl)boron Derivatives." In Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00735.

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Prakash, G. K. S., and J. Hu. "Compounds Containing a Trifluoromethyl Group." In Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-022-00730.

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Schmidbaur, H., and A. Schier. "With Bis(trifluoromethyl)cadmium." In Compounds of Groups 12 and 11 (Zn, Cd, Hg, Cu, Ag, Au), 1. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-003-00475.

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Pollex, A. "Using Trifluoromethyl Hypofluorite." In X-Ene-X (X=F, Cl, Br, I, O, S, Se, Te, N, P), Ene-Hal, and Ene-O Compounds, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-032-00448.

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Gennari, C., S. Ceccarelli, and U. Piarulli. "From Imide-Derived Vinyloxyboranes with Excess Dibutyl{[(trifluoromethyl)sulfonyl]oxy}borane." In Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00327.

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DesMarteau, Darryl D. "Trifluoromethyl peroxygen compounds: a personal review and perspective." In The Curious World of Fluorinated Molecules, 59–71. Elsevier, 2021. http://dx.doi.org/10.1016/b978-0-12-819874-2.00007-2.

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