Stereoselective one-pot synthesis of polycyanosubstituted piperidines

Stereoselective one-pot synthesis of polycyanosubstituted piperidines Full article

Journal

Monatshefte Fur Chemie
ISSN: 1434-4475 , E-ISSN: 0026-9247

Output data

Year: 2018, Volume: 149, Number: 11, Pages: 1979-1989 Pages count : 11 DOI: 10.1007/s00706-018-2187-x

Authors

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

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
2	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russian Federation

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.

Vereshchagin A.N. , Karpenko K.A. , Elinson M.N. , Gorbunov S.V. , Gordeeva A.M. , Proshin P.I. , Goloveshkin A.S. , Egorov M.P.
Stereoselective one-pot synthesis of polycyanosubstituted piperidines
Monatshefte Fur Chemie. 2018. V.149. N11. P.1979-1989. DOI: 10.1007/s00706-018-2187-x WOS Scopus OpenAlex

Web of science:	WOS:000446500100006
Scopus:	2-s2.0-85053415288
OpenAlex:	W2890321523

DB	Citing
OpenAlex	12
Scopus	14
Web of science	11