The photo-induced ring expansion of azido(methoxy)quinolines to methoxypyridoazepines
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2495-2500
- https://doi.org/10.1039/p19830002495
Abstract
The yields of 9-alkylamino-5H-pyrido[2,3-c]azepines from the photo-induced ring-expansion of 8-azidoquinoline in primary amines are increased significantly by the presence of a 6-methoxy group, which also for the first time induces ring-expansion of the azide in secondary amines. Optimum conditions have been found for the ring-expansion of 8-azidoquinoline in methanol–potassium methoxide to give 9-methoxy-5H-pyrido[2,3-c]azepine, and under the same conditions 8-azido-6-methoxy- and 6-azido-8-methoxy-quinoline ring-expand in excellent yield to the corresponding dimethoxypyridoazepines.Keywords
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