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Synthesis of heterocyclic compounds. XXIV. Synthesis of pyridines from β‐substituted α‐phenylacrylonitriles
Author(s) -
Fuentes L.,
Vaquero J. J.,
Soto J. L.
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190525
Subject(s) - chemistry , malononitrile , aryl , medicinal chemistry , sodium , organic chemistry , combinatorial chemistry , catalysis , alkyl
The reaction of malononitrile with α‐phenylcinnamonitriles in ethanolic sodium ethanethiolate is studied as a convenient route to 2‐amino‐4‐aryl‐5‐cyano‐6‐ethylthio‐3‐phenyl‐3,4‐dihydropyridines ( 5 ) and the corresponding pyridines 6 . From the study of the structure of 5a (Ar = Ph) we can conclude that this cyclization reaction proceeds via a site‐selective addition of the ethanethiolate to the cyano group i of the 1,3‐tricarbonitrile ( 2 ).