Synthesis of heterocyclic compounds. XXIV. Synthesis of pyridines from β‐substituted α‐phenylacrylonitriles | Zendy

Fuentes L. | Zendy; Vaquero J. J. | Zendy; Soto J. L. | Zendy

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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 ).

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