Synthesis of Tricyclic Benzazocines by Aza-Prins Reaction

Org Lett. 2017 Jan 6;19(1):266-269. doi: 10.1021/acs.orglett.6b03577. Epub 2016 Dec 16.

Abstract

The aza-Prins reaction of 3-vinyltetrahydroquinolines with aldehydes proceeded smoothly in the presence of hydrogen halides, and the tricyclic benzazocine derivatives were isolated in good to high yields. The reaction would proceed through the formation and cyclization of the iminium ion intermediate.