Penicillin-cephalosporin conversion IV. Direct synthesis of 3'-thiosubstituted cephalosporins from thiazoline-azetidinones

✍ Scribed by Sigeru Torii; Hideo Tanaka; Michio Sasaoka; Norio Saitoh; Takashi Siroi; Junzo Nokami

• Book ID: 104220877
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 183 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)87378-5

✦ Synopsis

Direct transformation of thiazoline-azetidinones 2, derived from penicillin G and V, into 3'-thio-substituted cephalosporins 4 has been performed by ring opening of the thiawline moiety with sulfenyl chlorides followed by ring closure with NH 3 in dimethylformamide and simultaneous displacement of the allylic chlorine atom with the leaving thiolates.