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Communication | Regular issue | Vol 14, No. 5, 1980, pp.589-592
Published online, 1st January, 1970
DOI: 10.3987/R-1980-05-0589
A Synthesis of 3-(α,β-Epoxy)-2-azatidinones Derivatives

Shinzo Kano,* Tsutomu Ebata, Yoko Yuasa, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Condensation of 1-phenyl-2-azetidinone with α-methylthio ketones yielded the corresponding β-hydroxy sulfides, which were converted to 3-(α,β-epoxy)-1-phenyl-2-azetidinones through two steps involving desulfurization of the sulfonium iodides. In a similar fashion, condensation of 1-phenyl-2-azetidinone with ethyl α-methylthioacetates gave the corresponding sulfenyl ketones, which were also converted to the 3-(α,β-epoxy)-2-azetidinone derivatives. These 2-azetidinones were further lead to α-anilinomethyl-1,2-butenolides by treatment with methanesulfonic acid.