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A general and versatile synthesis of 3‐phenylthio β‐lactams as lead molecules for 3‐methyl‐2‐azetidinones
Author(s) -
Kanwar Seema,
Sharma S. D.
Publication year - 2007
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.5570440523
Subject(s) - chemistry , ketene , stereoselectivity , cycloaddition , alkylation , raney nickel , imine , flue gas desulfurization , chloride , medicinal chemistry , organic chemistry , lactam , molecule , phosphorus , catalysis
Ketene‐imine cycloaddition using phosphorus oxychloride and benzenesulfonyl chloride under the described reaction conditions yielded trans 3‐phenylthio 2‐azetidinones in good yields. Desulfurization using Raney nickel and alkylation finally afforded trans 3‐methyl‐2‐azetidinones in a stereoselective manner.