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Reaction of ω‐cyanoacetophenone and some of its derivatives with secondary amines. New synthesis of aminopyridine derivatives
Author(s) -
Purrello G.,
Vullo A. Lo
Publication year - 1974
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.5570110406
Subject(s) - chemistry , morpholine , piperidine , pyrrolidine , electrophile , pyridine , carbanion , nucleophile , enamine , organic chemistry , medicinal chemistry , catalysis
ω‐Cyanoacetophenone (1a) and its derivatives 1b‐c react with morpholine (or piperidine) to give mainly 2,4‐diaryl‐3‐eyano‐6‐morpholino‐ (or piperidino‐) pyridine derivatives (5) ; relative β‐aminoeinnamonitriles 6 and very small amounts of amidines 4 are also obtained. When pyrrolidine is used compounds 5 cannot be detected and enamines 6 are the main product. A mechanism involving the intermediate formation of enamines 6 (as electrophiles) and of carbanions 11 (as nucleophiles) is proposed to explain this new synthesis of aminopyridine derivatives.