Benzoazepines and derivatives

Pentacyclic derivatives 48 of the benzoazepine (-)-clavizepine were synthesised using three different methods for the formation of the azepine ring including radical, palladium and Friedel-Crafts alkylation and acylation, the most successful being the latter. 07JOC8804 . 

A benzazepine derivative of homopipecolic acid 53 was formed by the reaction of an A-magnesioaryl amine with a magnesium carbenoid formed from 1-chloroalkyl p-tolyl sulfoxide 51. The intermediate 52 was trapped with ethyl chloroformate to yield the benzoazepine in good yield. In contrast, the corresponding azepine derivative was formed in only 4% yield 07TL7829 . 

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