Synthesis and Reactivity of Propargylamines in Organic Chemistry

Chemical Reviews, Год журнала: 2017, Номер 117(24), С. 14091 - 14200

Опубликована: Ноя. 22, 2017

Propargylamines are a versatile class of compounds which find broad application in many fields chemistry. This review aims to describe the different strategies developed so far for synthesis propargylamines and their derivatives as well highlight reactivity use building blocks chemically relevant organic compounds. In first part review, synthetic approaches synthesize propargylamines, such A3 couplings C–H functionalization alkynes, have been described organized on basis catalysts employed syntheses. Both racemic enantioselective reported. second part, an overview transformations into heterocyclic pyrroles, pyridines, thiazoles, oxazoles, other derivatives, is presented.

Язык: Английский

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Chemistry of Ketene N,S-Acetals: An Overview

Chemical Reviews, Год журнала: 2016, Номер 116(2), С. 287 - 322

Опубликована: Янв. 13, 2016

Push-pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are interest not only for their unique electronic properties but also importance as versatile building blocks in organic synthesis. In the world ketene acetals having push-pull alkene skeleton, N,S-acetal is most likely biggest family according to number types these compounds. The first compound was reported 1956. As cyclic compound, nithiazine, lead structure neonicotinoid insecticides, 1978. characteristics N,S-acetals, have structural feature S,S-acetals enaminones, make them easy use, especially cyclization multicomponent reactions synthesis various heterocyclic systems related natural products. There has been an increasing wealth information about synthetic applications especially, recent years. This review provides comprehensive knowledge on chemistry N,S-acetals.

Язык: Английский

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A new avenue to the synthesis of highly substituted pyrroles: synthesis from N-propargylamines

RSC Advances, Год журнала: 2016, Номер 6(22), С. 18619 - 18631

Опубликована: Янв. 1, 2016

Pyrroles have attracted much attention due to their potential biological activities.

Язык: Английский

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Synthesis of thioesters through copper-catalyzed coupling of aldehydes with thiols in water

Green Chemistry, Год журнала: 2013, Номер 15(9), С. 2476 - 2476

Опубликована: Янв. 1, 2013

Copper-catalyzed C–S bond formation between aldehydes and thiols in the presence of TBHP as an oxidant is described. Functional groups including chloro, trifluoromethyl, bromo, iodo, nitrile, ester thiophene are all tolerated by reaction conditions employed. This performed water without use a surfactant. Both aryl alkyl couple suitably with aryl- thiols, affording corresponding thioesters moderate to good yields.

Язык: Английский

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Transition Metal‐Catalyzed and Metal‐Free Cyclization Reactions of Alkynes with Nitrogen‐Containing Substrates: Synthesis of Pyrrole Derivatives

ChemCatChem, Год журнала: 2020, Номер 12(13), С. 3335 - 3408

Опубликована: Март 17, 2020

Abstract This review describes the efforts in synthesis of pyrrole derivatives using reaction alkynes with nitrogen‐compounds under transition metal‐catalyzed and metal‐free conditions, past decade. We initially focused on methods preparation reactions catalyzed by metal. In this part, we described syntheses 1‐pyrrolines, 2‐pyrrolines, 3‐pyrrolines, pyrroles, pyrrolidines following an alphabetical order metal used for synthesis. Subsequently, presented these conditions.

Язык: Английский

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Montmorillonite clay catalyzed synthesis of functionalized pyrroles through domino four-component coupling of amines, aldehydes, 1,3-dicarbonyl compounds and nitroalkanes

RSC Advances, Год журнала: 2013, Номер 3(44), С. 21736 - 21736

Опубликована: Янв. 1, 2013

An efficient and eco-friendly synthesis of functionalized pyrroles using recyclable montmorillonite clay K10 KSF catalysts has been described. The clay-catalyzed domino four-component coupling (4CC) amines, aldehydes, 1,3-dicarbonyl compounds nitroalkanes produced in good yields. developed methods offers advantages such as operational simplicity, economical, simple workup, use commercial catalyst excellent functional group compatibility to synthesize structurally diverse pyrroles. This is the first report on heterogeneous for this 4CC.

Язык: Английский

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Multicomponent reactions in PEG-400: ruthenium-catalyzed synthesis of substituted pyrroles

Tetrahedron Letters, Год журнала: 2014, Номер 55(43), С. 5932 - 5935

Опубликована: Сен. 10, 2014

Язык: Английский

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Synthesis of polysubstituted pyrroles via [3 + 2]-annulation of aziridines and β-nitroalkenes under aerobic conditions

Organic & Biomolecular Chemistry, Год журнала: 2013, Номер 12(8), С. 1351 - 1356

Опубликована: Дек. 20, 2013

Polysubstituted pyrroles were regioselectively synthesized in moderate to good yields via the copper acetate-catalyzed [3 + 2] annulation reaction of readily accessible aziridines and nitroalkenes. This was proposed proceed through a key azomethine ylide intermediate generated by selective C-C bond cleavage aziridine followed with nitroalkenes under aerobic conditions.

Язык: Английский

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Synthesis of multisubstituted 1H-pyrrole: selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide

Tetrahedron, Год журнала: 2014, Номер 70(29), С. 4395 - 4399

Опубликована: Май 2, 2014

Язык: Английский

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A base-catalyzed cycloisomerization of 5-cyano-pentyne derivatives: an efficient synthesis of 3-cyano-4,5-dihydro-1H-pyrroles

Chemical Communications, Год журнала: 2014, Номер 50(83), С. 12490 - 12492

Опубликована: Янв. 1, 2014

A base-catalyzed cycloisomerization of 5-cyano-pentyne bearing a terminal alkyne group has been developed under metal-free conditions. This reaction involves tandem process providing efficient access to 3-cyano-4,5-dihydro-1H-pyrroles in good excellent yields an atom-economic manner with 1,3-cyano migration as the key transformation.

Язык: Английский

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