The trapping of sulfenic acids from penicillin sulfoxides - use of 2,5-dimercapto-1,3,4-thiadiazole and 2,4-dimercaptopyrimidine as trapping agents.

✍ Scribed by Ronald G. Micetich; Samarendra N. Maiti; Maya P. Singh; M. Tanaka; T. Yamazaki; K. Ogawa

• Book ID: 104233342
• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 162 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80900-x

✦ Synopsis

used to trap sulfenic acids from penicillin sulfoxides. Kamiya et al1 first reported the preparation of unsymmetrical azetidinone disulfides Lfrom penicillin sulfoxides and utilized this disulfide L for the derivatization of the B-methyl group in penicillins. Since then, "Kamiya's disulfide" has found synthetic utility for the preparation of many other 2Bmethylpenam derivatives including triazolyl*, halol, azido2y3 substituted amino3, hydroxy4, alkoxy3 and nitroxy5. Though 2-mercaptobenzothiazole is a convenient thiol for the trapping of sulfenic acid from penicillin sulfoxide, our previous papers6-8 in this series have described the use of other substituted monothiols ranging from aliphatic to aromatic to heteroaromatic. However, part of the usefulness of these unsymmetrical disulfides as synthetic intermediates greatly depend on their ability to recyclise to the five membered thiazolidine ring system of the penam nucleus.