Studies on diazepines. XXIX. Syntheses of 3H-and 5H-1, 4-benzodiazepines from 3-azidoquinolines.

H SASHIDA, A FUJII, T TSUCHIYA

Index: Sashida, Haruki; Fujii, Akira; Tsuchiya, Takashi Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 10 p. 4110 - 4116

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Citation Number: 5

Abstract

Irradiation of the 3-azidoquinolines (6a-c) in the presence of sodium methoxide resulted in ring expansion to give the fully unsaturated 3-methoxy-3H-1, 4-benzodiazepines (8). Further treatment of the 2-unsubstituted 3H-1, 4-benzodiazepine (8a) with sodium methoxide in methanol gave the solvent adduct 7, which reverted to 8a on being refluxed in benzene, whereas the 2-substituted 3H-1, 4-benzodiazepines (8b, c), upon treatment with sodium ...