2‐Carboazetidine derivatives | Zendy

Rodebaugh Richard M. | Zendy; Cromwell Norman H. | Zendy

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2‐Carboazetidine derivatives

Author(s) -

Rodebaugh Richard M.,

Cromwell Norman H.

Publication year - 1971

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.5570080104

Subject(s) - chemistry , hydrazine (antidepressant) , hydrate , derivative (finance) , sequence (biology) , ring (chemistry) , alkyl , medicinal chemistry , organic chemistry , stereochemistry , chromatography , biochemistry , financial economics , economics

A reaction sequence is reported for converting methyl 7‐bromocrotonate to 1‐alkyl‐2‐carbo‐methoxyazetidines thus confirming our earlier structural assignments of these compounds obtained by a more direct route. Methods are described for obtaining azetidinyl alcohols, acids, amides, amines and ketones. 1‐ t ‐Butyl‐2‐carbomethoxyazetidine was observed to undergo ring opening to an acyclic γ‐aminohydrazide derivative when treated with hydrazine hydrate. On the other hand, the corresponding N ‐benzylazetidine under similar conditions rearranged to 1‐benzyl‐2‐pyrrolidinone.

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