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Ring‐opening and a novel ring expansion in the reactions of 1‐Alkyl‐2‐carbomethoxyazetidine with hydrazine
Author(s) -
Leung HiuKwong,
Phillips Barry A.,
Cromwell Norman H.
Publication year - 1976
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.5570130210
Subject(s) - chemistry , hydrazine (antidepressant) , hydrate , alkyl , ring (chemistry) , methanol , diimide , ethanol , medicinal chemistry , organic chemistry , polymer chemistry , molecule , perylene , chromatography
Abstract The mechanism of the reactions of 1‐ t ‐butyl‐2‐carbomethoxyazelidine and 1‐benzyl‐2‐carbomethoxyazetidine with hydrazine hydrate was investigated. Treatment of 1‐alkyl‐2‐earbomethoxyazetidine with hydrazine hydrate in cold ethanol yielded 1‐alkylazetidine‐2‐carhohydrazide. Depending on the sterie bulkiness of the alkyl group of the amino functionality, reactions of 1‐alkylazetidine‐2‐carbohydrazides in methanol gave the appropriate aminoester or the appropriate pyrrolidone, or a mixture of both. The intermediacy of the diimide in these transformations was confirmed by the concurrent reduction of azobenzene to hydrazobenzene.