Studies on diazepines. XXVII. Syntheses of fully unsaturated 1H-and 3H-1, 4-benzodiazepines from 4-quinolyl azides.

H SASHIDA, A FUJII, T TSUCHIYA

Index: Sashida, Haruki; Fujii, Akira; Tsuchiya, Takashi Chemical & Pharmaceutical Bulletin, 1987 ,  vol. 35,  # 8  p. 3182 - 3189

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Citation Number: 12

Abstract

Irradiation of the 4-azidoquinolines (7a-d) in a 1: 1 mixture of methanol and dioxane containing sodium methoxide resulted in ring expansion to form the unstable fully unsaturated 1H-1, 4-benzodiazepines (9a-d), which were tautomerized to the stable 3H-1, 4- benzodiazepines (10a-d) by further treatment with sodium methoxide. Acetylation of the 3H- diazepines (10a and 10d) resulted in tautomerization to afford the 1-acetyl compounds ...