Bibliographies thématiques / Enaminone synthesis

Littérature scientifique sur le sujet « Enaminone synthesis »

Auteur : Grafiati
Publié le 11 mars 2023

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Articles de revues sur le sujet "Enaminone synthesis"

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Chattopadhyay, Amit Kumar, et Stephen Hanessian. « Cyclic enaminones. Part II : applications as versatile intermediates in alkaloid synthesis ». Chemical Communications 51, no 92 (2015) : 16450–67. http://dx.doi.org/10.1039/c5cc05892a.

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Among many other strategies, the enaminone approach is an important strategy to construct and diversify the azacyclic core in various alkaloids syntheses. In this brief review we discuss the application of cyclic enaminones as building blocks, as well as potential intermediates in the total synthesis of selected alkaloids.
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Štanfel, Urša, Dejan Slapšak, Uroš Grošelj, Franc Požgan, Bogdan Štefane et Jurij Svete. « Synthesis of 6,7-Dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles by Azomethine Imine-Alkyne Cycloadditions Using Immobilized Cu(II)-Catalysts ». Molecules 26, no 2 (13 janvier 2021) : 400. http://dx.doi.org/10.3390/molecules26020400.

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A series of 12 silica gel-bound enaminones and their Cu(II) complexes were prepared and tested for their suitability as heterogeneous catalysts in azomethine imine-alkyne cycloadditions (CuAIAC). Immobilized Cu(II)–enaminone complexes showed promising catalytic activity in the CuAIAC reaction, but these new catalysts suffered from poor reusability. This was not due to the decoordination of copper ions, as the use of enaminone ligands with additional complexation sites resulted in negligible improvement. On the other hand, reusability was improved by the use of 4-aminobenzoic acid linker, attached to 3-aminopropyl silica gel via an amide bond to the enaminone over the more hydrolytically stable N-arylenamine C-N bond. The study showed that silica gel-bound Cu(II)–enaminone complexes are readily available and suitable heterogeneous catalysts for the synthesis of 6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazoles.
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Masaret, Ghada S., et Thoraya A. Farghaly. « Synthesis of 8,10-disubstituted-triazoloperimidines from (E)-3-(dimethylamino)-1-(8- phenyl-8H-[1,2,4]triazolo[4,3-a]perimidin-10-yl)prop-2-en-1-one and Their Antimicrobial Activity ». Current Organic Synthesis 15, no 1 (20 mars 2018) : 126–36. http://dx.doi.org/10.2174/1570179414666170601121137.

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Aim and Objective: Enaminones belay to be extremely stable compounds and constitute a versatile group of salutary precursors for the synthesis of enormous classes of organic compounds. So, in this context, we synthesized a new enaminone, namely, (E)-3-(dimethylamino)-1-(8-phenyl-8H-[1,2,4]triazolo[4,3- a]perimidin-10-yl)prop-2-en-1-one (enaminone 2). Materials and Methods: The reaction of enaminone 2 with different types of hydrazonoyl chlorides or hydrazine hydrate afforded new substituted pyrazoles. Also, the reaction of enaminone with 6-amino-2- thioxopyrimidin-4-one in acetic acid under reflux produced 2-thioxopyridopyrimidinone derivative. The latter thione derivative reacts with hydrazonoyl chlorides to give pyridotriazolopyrimidines. 5-(8-Phenyl-8H- [1,2,4]triazolo[4,3-a]perimidin-10-yl)isoxazole was produced from the reaction of enaminone 2 with hydroxylamine. Results & Conclusion: The structure of all the novel perimidine derivatives was confirmed on the basis of spectral data and elemental analyses. The enaminone and the newly synthesized compounds were tested for their antimicrobial activity, and the results obtained revealed that some derivatives are more potent than the reference drugs used.
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Ciber, Luka, Franc Požgan, Helena Brodnik, Bogdan Štefane, Jurij Svete et Uroš Grošelj. « Synthesis and Catalytic Activity of Organocatalysts Based on Enaminone and Benzenediamine Hydrogen Bond Donors ». Catalysts 12, no 10 (28 septembre 2022) : 1132. http://dx.doi.org/10.3390/catal12101132.

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A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl enaminones with (S)-quininamine (9 examples) and the 1,2-benzenediamine-type catalysts were prepared in 3 steps from (S)-quininamine and ortho-fluoronitrobenzene derivatives (15 examples). Their organocatalytic activity was evaluated in the Michael addition of acetylacetone to trans-β-nitrostyrene. Enantioselectivities of up to 72% ee were observed.
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Agamy, Samia Michel, Mervat Mohammed Abdel-Khalik, Mona Hassan Mohamed et Mohammed Hilmy Elnagdi. « Enaminones as Building Blocks In Heterocyclic Synthesis : A New One Pot Synthesis of Polyfunctional Substituted Pyridines ». Zeitschrift für Naturforschung B 56, no 10 (1 octobre 2001) : 1074–78. http://dx.doi.org/10.1515/znb-2001-1016.

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Enaminones react with a variety of active methyl and methylene reagents in presence of ammonium acetate to yield functionally substituted pyridines in good yields. The reaction proceeded via initial Michael addition across the double bond followed by cyclization. The reaction of enaminone with aromatic aldehyde in acetic acid/ammonium acetate afforded the dihydropyridine that was oxidized to the corresponding pyridine.
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Liu, Weibing, Cui Chen et Qing Zhang. « FeCl3-PTSA Co-Catalysed Highly Regio- and Stereo-Selective Synthesis of β-Functionalised Enamine Derivatives ». Journal of Chemical Research 36, no 3 (mars 2012) : 175–77. http://dx.doi.org/10.3184/174751912x13306054094882.

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β-Enaminone derivatives are useful synthetic precursors. β- N-Substituted ( E)-enaminones and β-N-substituted ( E)-aminoacrylates were synthesised with high regio- and stereo-selectivity via using the co-catalytic system of FeCl3/PTSA, which also provides a new way to the formation of C–O bond.
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Hassan, Mohamed M., et Mona H. Alhalafi. « Synthesis, Structural Determination, and Antioxidant Activities of Acyclic and Substituted Heterocyclic Phosphonates Linearly Linked 4-hydroxy-2(1H)-quinolinone ». Molecules 27, no 18 (13 septembre 2022) : 5960. http://dx.doi.org/10.3390/molecules27185960.

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The chemical reactivity of 3-[(E)-3-(dimethylamino)-2-propenoyl]-4-hydroxy-1-methy-2(1H)-quinolinone (1) towards some phosphorus reagents was studied. The enaminone 1 was cyclized into pyranoquinolinylphosphonate 2 via treatment with diethyl phosphite in basic medium. However, its reaction with triethoxy phosphonoacetate gave the substituted oxopyranylphosphonate 3. Using the same reaction conditions, both thioxopyridinylphosphonate 4 and oxopyranylphosphonate 5 were produced via a reaction of enaminone 1 with both diethyl 2-amino-2-thioxoethylphosphonate and diethyl vinylphosphonate, respectively, in low yields. In addition, the two novel oxopyridinylphosphonates 6 and 7 were obtained by treatment of enaminone 1 with a diethyl cyanomethylphosphonate reagent. Two oaxathiaphosphininyl derivatives, 8 and 9, were obtained by treatment of the enaminone 1 with O, O-diethyl dithiophosphoric acid under different reaction conditions. Diazaphosphininyl 11 and oxazaphosphininyl 12 derivatives were obtained in excellent yields using a P-phenylphosphonic diamide reagent under different reaction conditions. The treatment of the enaminone 1 with phosphorus pentasulfide produced the non-phosphorylated product thioxothiopyranoquinolinone 13. Finally, the enaminone was turned into oxathiaphosphininyl 14 using Lawesson’s reagent. The possible reaction mechanisms of the formation of these products were discussed. The structures of newly isolated products were established by elemental analysis and spectral tools. The compounds were evaluated for their antioxidant activities.
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Szafraniec, Anna, Marcin Grajda, Hanna Jędrzejewska, Agnieszka Szumna et Waldemar Iwanek. « Enaminone Substituted Resorcin[4]arene—Sealing of an Upper-Rim with a Directional System of Hydrogen-Bonds ». International Journal of Molecular Sciences 21, no 20 (11 octobre 2020) : 7494. http://dx.doi.org/10.3390/ijms21207494.

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The paper presents the synthesis of an enaminone resorcin[4]arene via a thermally activated o-quinomethide. The crystal structure indicates that in the solid state all enaminone units participate in a unidirectional seam of 12 intramolecular hydrogen bonds that are formed around the cavity. The molecule exhibits C2 symmetry, with two opposite-laying enaminone units directed inside the cavity (“in”), and the other two units outside the cavity (“out”). In the solution the enaminone resorcin[4]arene exists as a mixture of conformers with distribution controlled by temperature and solvent. The experimental data are compared with the results of theoretical calculations using DFT B3LYP/6-31G(d,p) and fast semi-empirical DFTB/GFN2-xTB method in various solvents.
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Al-Romaizan, Abeer N., Nesreen S. Ahmed et Sherin M. Elfeky. « Design, Synthesis, and Biological Evaluation of Triazolyl- and Triazinyl-Quinazolinediones as Potential Antitumor Agents ». Journal of Chemistry 2019 (3 février 2019) : 1–12. http://dx.doi.org/10.1155/2019/9104653.

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Novel 6(3-1H-1,2,4-triazol-1-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (7a–e) were synthesized from different enaminones (6a–e) with 6-hydrazinyl-3-phenylquinazoline-2,4(1H,3H)-dione. 2,6(4-2-Substituted-1,3,5-triazin-1(2H)-yl)-3-phenylquinazoline-2,4(1H,3H)-diones (8a–k) were synthesized from the reaction of 1-(2,4-dioxo-3-phenyl-1,2,3,4-tetrahydroquinazolin-6-yl)thiourea, urea, or guanidine (3a–c) with enaminones (6a–e), and a series from 3-substituted-2-imino-1,3,5-triazin-1(2H)-yl-sulfonyl-phenyl-1-methylquinazoline-2,4(1H,3H)-dione (12a–j) were obtained from the reaction of N-(diaminomethylene)-4-(1-methyl-2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)benzenesulfonamide (11) with the enaminone (6a–j). The antitumor activity of the synthesized compounds was evaluated against two human cell lines: human colon carcinoma HCT116 and human hepatocellular carcinoma HEP-G2. Some of the tested compounds showed significant potency compared to the reference drug staurosporin.
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Filkale, Adelew Estifanos, et Chandni Pathak. « Dinuclear cobalt complexes supported by biphenol and binaphthol-derived bis(salicylaldimine) ligands : synthesis, characterization and catalytic application in β-enaminone synthesis from 1,3-dicarbonyl compounds and aliphatic amines ». New Journal of Chemistry 44, no 35 (2020) : 15109–21. http://dx.doi.org/10.1039/d0nj00052c.

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Thèses sur le sujet "Enaminone synthesis"

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Ostric, Adrian. « Hydroxyethylene isosters of Xaa-Pro dipeptides : synthetic approaches and new HIV-PR inhibitors ». Doctoral thesis, Università degli studi di Trieste, 2011. http://hdl.handle.net/10077/4576.

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2009/2010
The aspartic protease (HIV-Pr) of the human immunodeficiency virus, responsible agent for AIDS, is surely one of the most studied enzymes in terms of structure and activity. HIV-Pr is responsible for cleaving the viral polyprotein precursor into structural proteins and enzymes and plays an essential role in the viral replication and maturation. HIV-Pr has thus become the target of numerous efforts to design antiviral therapeutic agents suitable for the treatment of AIDS. In the field of organic chemistry, the search for effective HIV-Pr inhibitors has boosted the development of new methodologies for the stereoselective synthesis of compounds containing multiple chiral centers, on which reversible inhibitors are generally based. HIV-Pr shows peculiar characteristics as it is able, unlike any other eukaryotic aspartic protease, to hydrolyze amide bonds with proline as the N-terminal residue. Moreover, it is active in a dimeric form, possessing C2 symmetry, in which each monomer contributes a catalytic aspartate. The first part of the present doctoral work described in Chapter 2, has been dedicated to the synthesis of hydroxyethylene Phe-Pro isosters in which the pyrrolidine ring is expanded by a condensed aromatic ring in order to provide a better fit to the enzyme’s catalytic site. During the synthesis of the isoster a novel reaction was discovered in which enaminones are directly formed by treatment of α,β-unsaturated ketones with trimethylsilylazide and fluoride. Phe-Pro isosters based on the enaminone structure showed moderate activity as HIV-Pr inhibitors. The direct amination of α,β-unsaturated ketones is the subject of Chapter 3. This reaction is demonstrated to be general for enones containing a β-hydrogen. A mechanism based on azide activation via formation of a pentacoordinated silicon species followed by a 1,3-dipolar cycloaddition is proposed and supported by experimental results and calculations. In Chapter 4 is reported the synthesis of a library of triazole inhibitors by a combinatorial approach based on click chemistry. The library was screened for HIV-Pr inhibition and deconvoluted. A set of promising members from the library was synthesized as single, enantiomerically pure compounds that confirmed to be active HIV-Pr inhibitors. Finally, in Chapter 5 the development of an alternative approach to dipeptide isosters, based on the ring closing metathesis of aminoacid-derived allylamines, is described. Building of the four carbon atom backbone of the isosteres is obtained after mounting the olefins on designed linkers that allow selectivity in the cross metathesis, and easy final cleavage. Carbamate linkers will also allow also protection of the amino groups during the next steps of the synthesis leading to the desired di- and monohydroxyethylene isosters.
La proteasi aspartica (HIV-PR) del virus della immunodeficienza umana, l'agente responsabile dell'AIDS, è sicuramente uno degli enzimi più studiati in termini di struttura e di attività. HIV-Pr è responsabile della scissione della poliproteina virale in proteine strutturali ed enzimi e svolge un ruolo essenziale nella replicazione e maturazione del virus. HIV-Pr è così diventato il bersaglio di numerosi studi mirati alla progettazione di agenti terapeutici antivirali adatti per il trattamento dell'AIDS. 
Nel campo della chimica organica, la ricerca di efficaci inibitori dell'HIV-Pr ha stimolato lo sviluppo di nuove metodologie per la sintesi stereoselettiva di composti contenenti più centri chirali, che costituiscono la base strutturale della maggior parte degli inibitori reversibili. 
HIV-Pr presenta caratteristiche peculiari in quanto è in grado, unica tra le proteasi aspartiche da eucarioti, di idrolizzare legami ammidici con la prolina come residuo N-terminale. Inoltre, l’enzima è attivo in una forma dimerica, con simmetria C2, in cui ogni monomero contribuisce con un residuo catalitico di acido aspartico. 
La prima parte del presente lavoro di dottorato, descritta nel capitolo 2, è stata dedicata alla sintesi di isosteri idrossietilenici del dipeptide Phe-Pro, contenenti un anello pirrolidinico espanso al fine di migliorare le interazioni con il sito catalitico dell'enzima. Durante la sintesi dell’ isostere è stata scoperta una nuova reazione di formazione di enaminoni per trattamento di chetoni α,β-insaturi con trimethylsilylazide e fluoruro. Alcuni isosteri Phe-Pro basati sulla struttura enaminonica hanno mostrato una moderata attività come inibitori della HIV-PR. 
L'amminazione diretta di chetoni -insaturi è il soggetto del capitolo 3. Questa reazione si è dimostrata essere generale per enoni contenente un idrogeno in posizione β. Un meccanismo basato sulla attivazione della azide attraverso la formazione di una specie pentacoordinata di silicio seguita da una cicloaddizione 1,3-dipolare viene proposto sulla base dei risultati sperimentali e di calcoli teorici. 
Nel capitolo 4 è riportata la sintesi di una libreria di inibitori triazolici ottenuti con un approccio combinatoriale. La libreria è stato analizzata per l'inibizione di HIV-Pr e deconvoluta. Alcuni membri promettenti della biblioteca sono stati sintetizzati come composti singoli, in forma enantiomericamente pura, confermandosi attivi inibitori della HIV-PR. 
Infine, nel capitolo 5, é descritto lo sviluppo di un approccio alternativo a isosteri di dipeptidi, basato sulla “ring closing methatesis” di allilamine derivate da aminoacidi. La costruzione dello scheletro degli isosteres si ottiene dopo l’assemblaggio delle olefine su un nuovo linker che consente una cross-metatesi selettività nonché un facile distacco del prodotto. Il linker può anche essere utilizzato come gruppo proteggente nella successiva elaborazione sintetica dei prodotti.
XXIII Ciclo
1981
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Sinibaldi, Marie-Eve. « Nouveaux intermediaires pour la synthese d'alcaloides pentacycliques : synthese totale de la desethyl-20 acetyl-20 aspidospermidine ». Clermont-Ferrand 2, 1988. http://www.theses.fr/1988CLF21144.

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Pereira, Fernando Luiz Cardoso. « Aplicações sintéticas de β-enamino ésteres ». Universidade de São Paulo, 2002. http://www.teses.usp.br/teses/disponiveis/46/46135/tde-19112015-162222/.

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Uma série de β-enamino ésteres foi submetida a reações de iodociclização ou lactonização mediada por iodo, fornecendo como produtos iodo-β-enamino ésteres cíclicos ou β-enamino lactonas, respectivamente. Os iodo-β-enamino ésteres cíclicos obtidos foram submetidos a reações de desidroiodação, fornecendo os correspondentes produtos de eliminação de HI a partir de iodociclos de cinco membros, e ciclopentanos trissubstituídos, a partir de anéis de seis membros. Esta última reação ocorreu por substituição nucleofílica intramolecular, em vez da esperada reação de desidroiodação. O efeito do N-substituinte, nestas reações, foi estudado para uma série de N-alquil e N-aril derivados, fornecendo dados que possibilitaram uma melhor compreensão dos mecanismos envolvidos. As β-enamino lactonas foram obtidas em baixos rendimentos, devido à formação de subprodutos decorrentes da poliiodação do substrato, e mostraram-se resistentes à redução da dupla ligação carbono-carbono por uma série de métodos testados. Um estudo de análise conformacional dos compostos bicíclicos nitrogenados também foi efetuado, através de dados espectroscópicos de RMN-1H e RMN-13C, com o auxílio de cálculos de mecânica molecular e semi-empíricos. Concluiu-se que em função do N-substituinte os biciclos adotam diferentes conformações preferenciais, o que altera significativamente seus perfis espectroscópicos.
A series of acyclic β-enamino esters was submitted to iodocyclization reactions or to iodine-mediated lactonization, leading to the corresponding cyclic iodo-β-enamino esters or β-enamino lactones. Dehydroiodination of the five-membered ring enamino esters furnished pyrrole, tetrahydroindole and hexahydroindole derivatives, under basic or neutral conditions. The six-membered ring enamino esters, when submitled to treatment with triethylamine, gave rise to trisubstituted cyclopentanes. This transformation occurred through an intramolecular nucleophilic substitution, instead of the expected dehydroiodination reaction. The effect of the N-substituent in these reactions was studied for a series for N-alkyl and N-aryl derivatives. The β-enamino lactones were obtained in poor yields, due to the poliiodination of the substrates, and showed to be resistent to reduction of the carbon-carbon double bond under several conditions. A study of conformational analysis of the bicyclic β-enamino esters was undertaken, using 1H-NMR and13C-NMR data, molecular mechanics and semi-empirical methods. From this study, it was observed that the bicyclic compounds adopt different conformations depending upon the N-substituent.
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González, Soria María José. « Selective synthesis and reactivity of indolizines ». Doctoral thesis, Universidad de Alicante, 2018. http://hdl.handle.net/10045/98672.

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Se ha llevado a cabo la síntesis multicomponente de una serie de 1-aminoindolizinas y pirrolo[1,2-a]quinolonas de manera efectiva a partir de derivados de 2-piridincarbaldehído, aminas secundarias y alquinos terminales utilizando CuNPs/C como catalizador en diclorometano a 70 ºC. La metodología se ha aplicado a una variedad de aminas y alquinos, los últimos incluyendo arilacetilenos así como alquilacetilenos, con rendimientos de moderados a altos. Dicho catalizador ha demostrado ser superior a una serie de catalizadores de cobre comerciales. Finalmente, se ha propuesto un mecanismo de reacción basado en la probada participación de aminas propargílicas como intermedios de reacción. Se han sintetizado indolizidinas a través de la hidrogenación catalítica heterogénea de indolizinas usando PtO2 como catalizador en ácido acético como disolvente y a una presión de 3,7 atm. Las indolizidinas se han obtenido con una elevada diastereoselectividad, incluso en el caso de poseer cuatro estereocentros. Se ha demostrado experimentalmente que la hidrogenación de la indolizina se produce a través del intermedio pirrólico 5,6,7,8-tetrahidroindolizina. Además, estas indolizidinas se han podido mono- o di-desbencilar usando un catalizador diferente. Se ha sintetizado una nueva familia de compuestos orgánicos por reacción de las indolizinas en medio ácido. Estos productos son tintes de indolizina de color violeta-rojizos que tienen una estructura D-A-π-A bien definida. La estructura de los tintes de indolizina se ha establecido mediante análisis de rayos X en estado sólido, pero se pueden distinguir dos rotámeros en disolución. Se ha propuesto un mecanismo de reacción en el que la propia indolizina actúa como nucleófilo y electrófilo; en éste, una molécula sufre hidrólisis en medio ácido y la adición Michael de la segunda molécula de indolizina. Un estudio de las características ópticas de estos tintes ha revelado un cambio de color dependiente del tamaño de partícula, un alto poder de coloración y un carácter solvatocrómico (es decir, que el color de la disolución del compuesto depende de la polaridad del disolvente usado), también en materiales plásticos. Finalmente, se ha estudiado la reactividad de las indolizinas con nitrosocompuestos, obteniendo dos productos diferentes según el sustituyente en la posición tres de éstas. En el caso de poseer un sustituyente aromático se obtienen β-enaminonas. Se ha realizado un estudio del alcance de esta metodología cambiando los sustituyentes 1, 3 y 6 de las indolizinas y usando compuestos nitrosoaromáticos con distintos sustituyentes en orto y para, obteniendo las correspondientes β-enaminonas con rendimientos aislados de moderados a buenos. El uso de esta metodología ha demostrado ser el más apropiado para obtener ese tipo de regioisómero, comparado con las metodologías clásicas de condensación de compuestos 1,3-dicarbonilos con aminas que dan el regioisómero opuesto. Para sustituyentes alifáticos, se han obtenido pirroles tetrasustituidos con rendimientos de moderados a buenos, variando los cuatro sustituyentes en la estructura de pirrol. Se han llevado a cabo varios experimentos para elucidar el mecanismo de reacción. Se ha demostrado que proceden vía iónica, no radicalaria. La presencia de agua es beneficiosa para la obtención de β-enaminonas, en cambio, una atmósfera de oxígeno o de argón no lo son. Con todo ello, se ha propuesto un mecanismo para la obtención de éstas en el que participa una estructura de isooxazol como intermedio. En el caso de los pirroles, se ha demostrado que hay una migración de la dibencilamina en la estructura. Tras varios experimentos, enfocados en la obtención de un posible intermedio de reacción, se ha propuesto la secuencia del mecanismo para la obtención de pirroles. En primer lugar, se ha propuesto el ataque nucleófilo al nitrosocompuesto, abriendo la estructura y perdiendo dibencilamina, formando así una cetona α,β-insaturada, seguido del ataque de la dibencialamina y posterior ciclación para la obtención del pirrol.
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Throup, Adam Eric. « Synthetic methodology and application of enamine [2+2] cyclisations for cyclobutane synthesis : development of integrin antagonists as anticancer therapeutics towards a total synthesis of providencin ». Thesis, University of Bradford, 2015. http://hdl.handle.net/10454/14411.

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Cyclobutanes represent an underutilised structural feature in medicinal chemistry, partially due to difficulties in forming them in an easy and controlled manner. Herein is described their application to a drug discovery project and development of the enamine [2+2] cyclisation; a straightforward synthesis of functionalised cyclobutanes. A library of 30 cyclobutane based integrin antagonists have been designed and synthesised to explore the SAR around the hit dual β3 integrin antagonist ICT9055. Several of which were shown to be highly potent antagonists inhibiting cancer cell adhesion, migration and invasion while remaining non-toxic. ICT9072 had comparable β3 activity to hit compound ICT9055 but also had activity against αvβ5 and therefore showed greater inhibition of migration of DLD-1 cells. This showed the ability to modify this scaffold for multi integrin antagonism and potential benefit of this. Synthetic studies towards the marine natural product providencin has led to the development of a previously unknown intramolecular enamine [2+2] cyclisation which has been shown to proceed in a diastereoselective manner. This reaction has been applied to the synthesis of a highly functionalised enatiopure cyclobutene suitable for inclusion into the total synthesis. A model furyl cyclobutane has also been synthesised to exemplify the route from the enantiopure cyclobutene through to the furyl cyclobutane fragment of providencin.
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Throup, Adam E. « Synthetic Methodology and Application of Enamine [2+2] Cyclisations for Cyclobutane Synthesis. Development of Integrin Antagonists as Anticancer Therapeutics Towards a Total Synthesis of Providencin ». Thesis, University of Bradford, 2015. http://hdl.handle.net/10454/14411.

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DELBECQ, PHILIPPE. « Nouvelles voies d'acces aux beta-enaminones cycliques. Application a la synthese de la six-methylpelletierine ». Paris 6, 1990. http://www.theses.fr/1990PA066472.

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La decarboxylation de beta-enaminocetoesters cycliques par thermolyse en presence d'acide orthoborique permet d'acceder a des beta-enaminones variees. La desacylation de beta-enaminodicetones par le methylate de sodium conduit a des resultats analogues. La reduction de la liaison ethylenique de beta-enaminones cycliques mene a des alcaloides cycliques comme la six-methylpelletierine
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Sevenich, Adrian Manuel [Verfasser]. « Entwicklung und Anwendung photochemischer Reaktionen zur Synthese und Modifikation von Heterocyclen : Synthese von (−)-Hexahydrofurofuranol ; Synthese und Funktionalisierung von Enaminonen / Adrian Manuel Sevenich ». Mainz : Universitätsbibliothek der Johannes Gutenberg-Universität Mainz, 2021. http://d-nb.info/122704853X/34.

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Taylor, Jane M. « The design and synthesis of acylated enamino esters as potential inhibitors of serine proteases ». Thesis, University of Canterbury. Chemistry, 1993. http://hdl.handle.net/10092/8000.

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This thesis examines the synthesis of bromo acylatad enamino asters, of the type (4.01), and protio acylatad enamino esters, of the type (4.02), designed as a new class of potential mechanism-based inactivators and alternate substrata inhibitors, respectively, of chymotrypsin. [Diagram] Chapter 1 describes the synthesis of succinic-, glutaric- and phthalic-basad, bromo and chloro enollactones (1.11-1.15, 1.17) via a new reaction involving halo enollactonization of keto acid phosphoranes (1.06-1.10). The phthalic bromo enollactones (1.17) are also synthesized via the reaction of Ph₃P=CBrCO₂Et with 4,5-dichlorophthalic anhydride. The reactions are extensions of the SCOOPY and Wittig anhydride carbonyl olefination reactions. Chapter 2 describes the synthesis of simple succinimide- and phthallmide-based protio and chloro enamino asters (2.09, 2.63-2.75, 2.93, 2.95, 2.98) via a versatile new reaction in which an enollactone (2.33, 1.11, 2.115) and amine react to form an isolable keto-amide (2.37-2.47, 2.94, 2.96, 2.116) and/or hydroxy lactam (2.48-2.50, 2.97) intermediate. Subsequent elimination of H₂O on heating gives the enamino aster via an overall insertion process. Chapter 3 describes the synthesis of simple succinimide-basad protio and bromo enamino asters (2.66, 2.71, 3.02-3.03) from the reaction of β-keto ester (3.01), via an isolable enamine intermediate (3.07-3.10). The synthesis of α 3-substituted enamino aster (3.04) via the insertion and β-keto ester routes is also described. Chapter 4 describes the synthesis of the target 3,3-disubstituted enamino esters (4.01-4.07) via the insertion reaction and a TiCl₄ mediated β-keto ester reaction. The benzyl group at position 3, required for recognition by chymotrypsin, is introduced stereoselectively using methodology developed largely by Seebach and coworkers for the asymmetric synthesis of α,α;-disubstituted amino acids. By changing this residue other serine proteases can be targeted. The proposed inhibitors (4.01-4.07) are designed to be incorporated into an oligopeptide having optimum interaction with the target enzyme. Preliminary testing of enamino esters and enollactones (2.71, 3.04, 4.01- 4.02, 4.03, 4.06, 4.42, 4.43) for chymotrypsin Inhibition is also described. Chapter 5 examines trends in the ¹³CNMR, ³¹PNMR and FAB mass spectra of keto acid and keto ester phosphoranes (4.15, 4.26, 4.40-4.41, 5.04-5.06); key intermediates to enamino esters and enollactones (eg 4.01-4.06, 4.42, 4.43).
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Deng, Yongming. « Asymmetric cyclization reactions through an enamine/acid cooperative approach. Synthesis of unsymmetrically functionalized benzoporphyrins ». Miami University / OhioLINK, 2014. http://rave.ohiolink.edu/etdc/view?acc_num=miami1406213121.

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Chapitres de livres sur le sujet "Enaminone synthesis"

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Waser, Mario. « Enamine Catalysis ». Dans Asymmetric Organocatalysis in Natural Product Syntheses, 7–44. Vienna : Springer Vienna, 2012. http://dx.doi.org/10.1007/978-3-7091-1163-5_2.

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Murphy, John J., Mattia Silvi et Paolo Melchiorre. « Enamine-Mediated Catalysis (n?→?π*) ». Dans Lewis Base Catalysis in Organic Synthesis, 857–902. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2016. http://dx.doi.org/10.1002/9783527675142.ch17.

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Waser, Mario. « Combined Iminium-Enamine Catalyzed Approaches ». Dans Asymmetric Organocatalysis in Natural Product Syntheses, 69–75. Vienna : Springer Vienna, 2012. http://dx.doi.org/10.1007/978-3-7091-1163-5_4.

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Fustero, Santos, Juan F. Sanz-Cervera, Julio Piera, María Sánchez-Roselló, Diego Jiménez et Gema Chiva. « Fluorinated β-Enamino Esters as Versatile Synthetic Intermediates : Synthesis of Fluorinated β-Amino Acids and Uracils ». Dans ACS Symposium Series, 593–610. Washington, DC : American Chemical Society, 2005. http://dx.doi.org/10.1021/bk-2005-0911.ch034.

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Dekeukeleire, S., M. D'hooghe et N. De Kimpe. « Synthesis from Enaminones ». Dans Heteroatom Analogues of Aldehydes and Ketones, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-127-00106.

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DeRosa, Thomas F. « Enaminones ». Dans Advances in Synthetic Organic Chemistry and Methods Reported in US Patents, 261–64. Elsevier, 2006. http://dx.doi.org/10.1016/b978-008044474-1/50032-3.

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Lue, Ping, et John V. Greenhill. « Enaminones in Heterocyclic Synthesis ». Dans Advances in Heterocyclic Chemistry, 207–343. Elsevier, 1996. http://dx.doi.org/10.1016/s0065-2725(08)60072-0.

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Keller, P. A. « Resin-Supported Synthesis of Enaminones ». Dans Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-015-00553.

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Woyciechowska, M., O. El-Sepelgy et J. Mlynarski. « Enamine-Based Direct Aldol Reactions ». Dans Water in Organic Synthesis, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-206-00276.

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Muchalski, H., et J. N. Johnston. « Iminium–Enamine Catalysis ». Dans Stereoselective Synthesis 1 Stereoselective Reactions of Carbon—Carbon Double Bonds, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-201-00082.

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Actes de conférences sur le sujet "Enaminone synthesis"

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Cunha, Silvio, et Raimundo Francisco dos Santos Filho. « Microwave induced multicomponent synthesis of 2-pyrrolo-3’-yloxindoles through reaction of enaminone, isatin and phosphorus ylide ». Dans 15th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013913142652.

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talbi, soumaya, souad rabi, hafid Abderrafia et mostafa khouili. « Efficient Synthesis of Pyrazolo-Enaminone Derivatives and Evaluation of Their Biological Activities ». Dans 1st International Electronic Conference on Catalysis Sciences. Basel, Switzerland : MDPI, 2020. http://dx.doi.org/10.3390/eccs2020-07540.

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Marques, Monique Ferreira, et Silvio Cunha. « Synthesis of Cyclic Azo- and Hydrazo-Enaminones ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0305-1.

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Marques, Monique F., et Silvio Cunha. « Synthesis of polisubstituted 1,3-azadienes from enaminones ». Dans 15th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013913141011.

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Gomes, Amenson T., et Silvio Cunha. « Synthesis of Acyclic -Enaminones Through Reaction of Enones and Benzyl Azide ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0333-1.

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Hortelan, Cristiane Regina Winck, Ingridhy Ostaciana Maia Freitas da Silveira, Silvia Mendes de Souza, Adilson Beatriz, Roberto da Silva Gomes et Nelson Luís de Campos Domingues. « Synthesis of β-enaminones catalyzed by nanoparticles of Fe2O3 in ultrasound and solvent-free approach. » Dans 15th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-15bmos-bmos2013_2013816163722.

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Andrighetto, Rosália, Helio G. Bonacorso, Jussara Navarini, Nícolas Krüger, Marcos A. P. Martins et Nilo Zanatta. « Highly Efficient Synthesis of CF3-Containing 7-Aminoquinolines From Cyclocondensation Reaction of Trifluoroacetyl Enamine Precursors ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0008-1.

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Santos, Airam O., José Tiago Menezes Correia et Silvio Cunha. « Synthesis of pyrrolizidines, indolizidines and pyrroloazepines through formal aza-[3+3] and aza-[3+2] cycloadditions of enaminones with maleic anhydride and maleimides ». Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0315-1.

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Santana, Lourenço Luis Botelho de, et Silvio Cunha. « Aza-bicycles Synthesis Through Formal Aza [3+3], [3+2+1] and [3+1+1+1] Cycloadditions Between Enaminones, Aldehydes and Meldrum’s Acid Derivatives. » Dans 14th Brazilian Meeting on Organic Synthesis. São Paulo : Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0056-1.

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Rezali, Nurul Syafiqah. « The Syntheses Of Fused Cyclic 5/6-Membered Ring Lactams Via Enamine Hydrogenation ». Dans 8th International Conference on Multidisciplinary Research 2019. European Publisher, 2020. http://dx.doi.org/10.15405/epsbs.2020.03.03.87.

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