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Communication | Regular issue | Vol 12, No. 6, 1979, pp.735-740
Published online, 1st January, 1970
DOI: 10.3987/R-1979-06-0735
Synthetic Studies on β-Lactam Antibiotics. IV. Synthesis of 1,9b-Dihydro-2H,4H-2-oxo-azeto[1,2-c][1,3]benzopxazine Derivatives

Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Kikuo Wakisaka, Hideo Sugi, and Keizo Tanigawa

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Synthesis of novel tricyclic β-lactams, 1,9b-dihydro-2H,4H-2-oxo-azeto[1,2-c][1,3]benzoxazines (14 and 15), was achieved by a cycloaddition reaction of 2-(4-chlorophenyl)-4-methylthio-2H-1,3-benzoxazine (12) with phenoxyketene followed by desulphurisation of the product (13).
This paper also describes a synthetic approach to an azeto[1,2-c][1,3]benzoxazine through reaction of an acyclic imine with ketene.