Four-component stereoselective synthesis of tetracyano-substituted piperidines

Four-component stereoselective synthesis of tetracyano-substituted piperidines Full article

Journal

Research on Chemical Intermediates
ISSN: 0922-6168 , E-ISSN: 1568-5675

Output data

Year: 2018, Volume: 44, Number: 9, Pages: 5623-5634 Pages count : 12 DOI: 10.1007/s11164-018-3444-7

Authors

Vereshchagin Anatoly N. ¹ , Karpenko Kirill A. ¹ , Elinson Michail N. ¹ , Goloveshkin Alexander S. ² , Ushakov Ivan E. ² , Egorov Mikhail P. ¹

Affiliations

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

A novel four-component stereoselective synthesis of polysubstituted piperidines is reported. The Knoevenagel–Michael–Mannich cascade of two equivalents of aromatic aldehydes, formaldehyde, two equivalents of malononitrile and ammonium acetate provides convenient access to the 2,6-diaryl-3,3,5,5-tetracyanopiperidines in good to excellent yields. Ammonium acetate plays a role both as a catalyst and as a nitrogen source. The formation of products is highly stereoselective. Structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, IR, elemental analysis and mass spectral studies. 2,6-diphenylpiperidine-3,3,5,5-tetracarbonitrile was characterized by X-ray diffraction.

Vereshchagin A.N. , Karpenko K.A. , Elinson M.N. , Goloveshkin A.S. , Ushakov I.E. , Egorov M.P.
Four-component stereoselective synthesis of tetracyano-substituted piperidines
Research on Chemical Intermediates. 2018. V.44. N9. P.5623-5634. DOI: 10.1007/s11164-018-3444-7 WOS Scopus OpenAlex

Web of science:	WOS:000441789200041
Scopus:	2-s2.0-85046040774
OpenAlex:	W2803032811

DB	Citing
OpenAlex	18
Scopus	19
Web of science	19