Title: Stereoselective one-pot synthesis of polycyanosubstituted piperidines
Author:
Vereshchagin, Anatoly;
Karpenko, Kirill;
Elinson, Michail;
Gorbunov, Sergey;
Gordeeva, Alexandra;
Proshin, Pavel;
Goloveshkin, Alexander;
Egorov, Mikhail
Subject:
Multicomponent reaction ; Polysubstituted piperidines ; Aromatic aldehydes ; Benzylidenemalononitriles ; Stereoselectivity
Description:
To access, purchase, authenticate, or subscribe to the full-text of this article, please visit this link: http://dx.doi.org/10.1007/s00706-018-2187-x Byline: Anatoly N. Vereshchagin (1), Kirill A. Karpenko (1), Michail N. Elinson (1), Sergey V. Gorbunov (1), Alexandra M. Gordeeva (1), Pavel I. Proshin (1), Alexander S. Goloveshkin (2), Mikhail P. Egorov (1) Keywords: Multicomponent reaction; Polysubstituted piperidines; Aromatic aldehydes; Benzylidenemalononitriles; Stereoselectivity Abstract: Abstract 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. Graphical abstract Author Affiliation: (1) 0000 0001 2192 9124, grid.4886.2, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation (2) 0000 0001 2192 9124, grid.4886.2, A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation Article History: Registration Date: 15/03/2018 Received Date: 22/01/2018 Accepted Date: 14/03/2018 Online Date: 04/09/2018 Article note: Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00706-018-2187-x) contains supplementary material, which is available to authorized users.
Is part of:
Monatshefte für Chemie - Chemical Monthly, 2018, Vol.149(11), pp.1979-1989
Identifier:
0026-9247
(ISSN); 1434-4475
(E-ISSN); 10.1007/s00706-018-2187-x
(DOI)