New synthesis of diazepam and the related 1, 4-benzodiazepines by means of palladium-catalyzed carbonylation

…, M Mori, T Ikeda, M Terashima, Y Ban

Index: Ishikura, Minoru; Mori, Miwako; Ikeda, Toshihito; Terashima, Masanao; Ban, Yoshio Journal of Organic Chemistry, 1982 , vol. 47, # 12 p. 2456 - 2461

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Citation Number: 31

Abstract

12 u metabolites 3, lO-dehydrocyclopeptine (6), dl-cyclopeptine (7), dl-cyclopenin (8), and dl- cyclopenol (9) by this method. For the synthesis of diazepam, commercially available p- chloroaniline was chosen as the starting material. N-Methylation of p-chloroaniline by the established method4 followed by bromination gave la in good yield. This was condensed with N-(benzyloxycarbony1) glycyl chloride (2a) to give the compound 10 (Scheme 11). ...