Condensed heterotricycles: IO,II-ring-annealed dibenz[b, f][I,4]oxazepines

Nagarajan, K. ; Shah, R. K. (1974) Condensed heterotricycles: IO,II-ring-annealed dibenz[b, f][I,4]oxazepines Indian Journal of Chemistry, 12 . pp. 263-269. ISSN 0019-5103

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Reaction of iminochloride 7 with ethanolamine yields 11, which is transformed into the imidazodibenzoxazepine (12) by successive treatment with phosphorous oxychloride and alkali. Iminochlorides 7-10 are likewise converted into γ-hydroxypropylamines such as ^3 and thence into pyrimidodibenzoxazepines (15-18). Iminochloride 9 and δ-hydroxybutylamine likewise afforded 30, which is transformed to~the chlorobutyl derivative (31) and then cyclized to the diazepinodibenzoxazepine (32). The mercaptotriazolodibenzoxazepine (34) is obtained by fusion of the thione (33) with thiosemicarbazide. Hydrazinodibenzoxazepine (35) is obtained from the iminochloride 7, and then converted to the triazolodibenzoxazepines (38-44). The action of sodium azide on iminochlorides 7 and 9 leads to the formation of tetrazolodibenzoxazepines 45 and 46 respectively. 48 could not be cyclized to the pyrrolodibenzoxazepine (49). During the formation of iminochloride 9, an interesting benzoxazole (29) is obtained. In the reactions of 9 with amines, similar benzoxazoles 22, 24 and 27 are obtained as byproducts. Mechanisms for the formation of these benzoxazoles are suggested.

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