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Communication | Regular issue | Vol 14, No. 5, 1980, pp.601-609
Published online, 1st January, 1970
DOI: 10.3987/R-1980-05-0601
Facile Synthesis of 2-Azetidinones with an Olefinic Substituent at the C-4 Position

Masayuki Shibuya* and Seiju Kubota

*Faculty of Pharmaceutical Sciences, University of Tokushima, Sho-machi 1, Tokushima 770-8505, Japan


A novel, facile synthesis of 2-azetidinones having an olefinic side chain at the C-4 position is described. Isoxazolones (7) derived from β-keto esters (6) were converted to β-amino esters (8) in excellent yield by reduction with sodium in isopropyl alcohol followed by esterification. Then reaction of the β-amino esters with o-tolylmagnesium bromide in dichloromethane gave the desired 2-azetidinones (2) ~ (5).