Studies on Diazepines. XXIX. Syntheses of 3H- and 5H-1,4-Benzodiazepines from 3-Azidoquinolines(Organic,Chemical)

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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 methoxide, underwent tautomerization to afford the 5H-1,4-benzodiazepines (15). Some reactions of the new 1,4-benzodiazepines (8 and 15) thus obtained were also examined.

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