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Communication | Regular issue | Vol 16, No. 9, 1981, pp.1491-1494
Published online, 1st January, 1970
DOI: 10.3987/R-1981-09-1491
New Synthesis of Diazepinone Skeleton Using Palladium Catalyzed Carbonylation

Miwako Mori, Minoru Ishikura, Toshihito Ikeda, and Yoshio Ban*

*Faculty of Pharmaceutical Sciences, Hokkaido University, Hokkaido University

Abstract

Palladium catalyzed carbonylation to the secondary amine (10) which was easily prepared from N-methyl-2-bromo-4-chloroaniline (1a) and carbobenzyloxyglycine (2a) gave 3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione derivative (11) in the yield of 30%. N-Acetyl derivative (14) of 8 was treated in the same manner to give the cyclic imide (15) in a fairly good yield and its result constitutes a new synthesis of diazepam (16).