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Synthesis of peptides containing 1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid. Part 3 . Cyclization of dipeptides and amides with acetic anhydride
Author(s) -
Zecchini Giampiero Pagani,
Paradisi Mario Paglialunga
Publication year - 1979
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.5570160815
Subject(s) - mesoionic , chemistry , acetic anhydride , carboxylic acid , acetic acid , organic chemistry , pummerer rearrangement , lactam , catalysis
Treatment of protected dipeptides containing 1,2,3,4‐tetrahydroquinoline‐2‐carboxylic acid with acetic anhydride affords only 1 H ,3 H ,5 H ‐oxazolo[3,4‐ a ]quinolin‐3‐one derivatives. The formation of a ‐acylaminomethylketones, arising from the competitive Dakin‐West reaction, was generally observed when the cyclization procedure was extended to some amides of the cyclic imino acid. The preferential stabilization of one of two probable mesoionic intermediates seems to determine the preferred pathway.