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Report | Regular issue | Vol 23, No. 3, 1985, pp.677-681
Published online, 1st January, 1970
DOI: 10.3987/R-1985-03-0677
New Synthesis of Functionalized β-Lactams from Azabutadiene Analogues and Ester Enolates

Mitsuo Komatsu, Shinji Yamamoto, Yoshiki Ohshiro,* and Toshio Agawa

*Department of Applied Chemistry, Faculty of Engineering, Osaka University, 2-1 Yamadaoka, Toyonaka, Osaka 560-0043, Japan


Reaction of the 2-azabutadiene 1 with α-lithioesters 2a,b gave N-styryl-2-azetidinones 3a,b in high yields in contrast to the δ-lactam formation of 1-azadienes with 2. The azines 7a,b also reacted with the enolate 2a to result in β-lactam formation: N-alkylidenamino-2-azetidinones 8a,b and/or 1,1’-bi(2-azetidinone)s 9a,b were obtained in good yields.