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Paper | Regular issue | Vol 87, No. 7, 2013, pp.1519-1536
Published online, 21st May, 2013
DOI: 10.3987/COM-13-12729
Synthesis of Dihydro-1-benzazepines

Meng-Yang Chang,* Chieh-Kai Chan, and Shin-Ying Lin

*Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, R.O.C.

Abstract

A synthetic route toward the benzannulated dihydro-1-benzazepines (8) with two oxygenated groups starting with 2-methoxy-5-nitrophenol (2) in high total yield is described. Two key routes are carried by Claisen rearrangement of allyl phenyl ethers (3) and ring-closing metathesis of dienes (7).