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β‐lithiations of carboxamides. Synthesis of β‐substituted‐α,β‐unsaturated amides
Author(s) -
Katritzky Alan R.,
Szajda Maria,
Lam Jamshed N.
Publication year - 1993
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.5570300515
Subject(s) - chemistry , alkylation , halide , benzotriazole , butyllithium , alkyl , organic chemistry , lactam , medicinal chemistry , catalysis
N ‐Methyl‐2‐methyl‐3‐(benzotriazol‐l‐yl)propanamide, on treatment with butyllithium forms a dianion which on treatment with alkyl and benzyl halides, aldehydes and ketones affords monosubstituted products; with ethyl p ‐toluate, a lactam is formed. The alkylated derivatives eliminate benzotriazole in the presence of base to afford trisubstituted α,β‐unsaturated amides.