Process for the preparation of imino-bridged benzocycloheptapyri

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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424256, 542429, 542455, 546 93, C07D47118

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active

042568897

ABSTRACT:
Benzocycloheptapyridines with an imine bridge in the cycloheptane ring, derivatives and pharmaceutically acceptable salts thereof are useful as anxiolytics, antidepressants, anticonvulsants, muscle relaxants and in the treatment of mixed anxiety-depression, minimal brain dysfunction and extrapyramidal disorders such as Parkinson's disease. They are prepared, for example, by treatment of a benzo[5,6]cyclohepta[1,2-c]pyridin-11-one with ammonia to give the 11-imine, acylation of the imine, treatment of the protected imine with an alkyllithium to provide the 11-alkyl-11-acylamino compound, treatment with acid or base to cause ring closure to an 11-alkyl-6,11-acylimino compound followed by removal of the protecting group, either hydrolytically or hydrogenolytically.

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Patai, S., The Chemistry of the Carbon--Nitrogen Double Bond, Interscience, London, 1970, pp. 67-68.
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Villani,F., et al., J. Het. Chem., 9, 1203-1207 (1972).
Villani, F., et al., J. Het. Chem., 8, 73-81 (1971).

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