Regioselective reactions of mesyloxymethylazetidinones with nucleophiles I. Cleavage of the azetidinone ring, azetidinone‐aziridine ring transformations | Zendy

Boros Éva | Zendy; Bertha Ferenc | Zendy; Fetter József | Zendy; Czira Gábor | Zendy; Feller Antal | Zendy; Simig Gyula | Zendy; KajtárPeredy Mária | Zendy

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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.

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