Stereoselective one-pot synthesis of polycyanosubstituted piperidines

被引：11

作者：

Vereshchagin, Anatoly N. ^{[1
]}

Karpenko, Kirill A. ^{[1
]}

Elinson, Michail N. ^{[1
]}

Gorbunov, Sergey V. ^{[1
]}

Gordeeva, Alexandra M. ^{[1
]}

Proshin, Pavel I. ^{[1
]}

Goloveshkin, Alexander S. ^{[2
]}

Egorov, Mikhail P. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow, Russia

[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow, Russia

来源：

MONATSHEFTE FUR CHEMIE | 2018年 / 149卷 / 11期

基金：

俄罗斯科学基金会;

关键词：

Multicomponent reaction; Polysubstituted piperidines; Aromatic aldehydes; Benzylidenemalononitriles; Stereoselectivity; RETRO-KNOEVENAGEL-REACTION; MULTICOMPONENT REACTIONS; ELECTROCATALYTIC TRANSFORMATION; AROMATIC-ALDEHYDES; MELDRUMS ACID; MALONONITRILE; CHEMISTRY; DIVERSITY; ALKALOIDS; CASCADE;

D O I：

10.1007/s00706-018-2187-x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An effective and facile multicomponent method for the synthesis of polysubstituted piperidines is described. The Michael-Mannich type cascade of benzylidenemalononitriles with aromatic aldehydes and ammonium acetate or aqueous ammonia provides convenient access to the stereoselective synthesis of 3,3,5,5-tetracyano-2,4,6-triarylpiperidines in good to excellent yields in one-pot manner. Ammonium acetate or aqueous ammonia plays a role both as a catalyst and as a nitrogen source. It is established that the reaction proceeds via sequence of equilibriums and a competitive mechanisms are implemented. [GRAPHICS] .

引用

页码：1979 / 1989

页数：11

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