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Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone‐aziridine ring transformations
Author(s) -
Boros Éva,
Bertha Ferenc,
Fetter József,
Czira Gábor,
Feller Antal,
Simig Gyula,
KajtárPeredy Mária
Publication year - 2006
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.5570430114
Subject(s) - aziridine , chemistry , regioselectivity , cleavage (geology) , sodium methoxide , nucleophile , electrophile , ring (chemistry) , bond cleavage , stereochemistry , lactam , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
The reaction of 4‐mesyloxymethylazetidin‐2‐one derivatives 3 with ammonia and sodium methoxide was investigated. The two electrophilic centers of the substrate reactesuccessively, resulting in cleavage of the lactam bond and formation of a new aziridine ring. The resulting type 6 and 8 aziridinylacetic acid derivatives are related to the novel 2‐(aziridin‐2‐yl)‐3‐phenylpropionic acid type carboxypeptidase A inhibitors and, as such, potential drug candidates.