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Paper | Regular issue | Vol 26, No. 6, 1987, pp.1595-1601
Published online, 1st January, 1970
DOI: 10.3987/R-1987-06-1595
1-Oxotetrahydro-2-benzazepines from 1-Methyl-3,4-dihydro-5H-2-benzazepines: Synthesis of N-Methyl-7,8,9-trimethoxy-2,3,4,5-tetrahydro-1H-2-benzazepine

Ricardo Alonso, Kimio Takahashi, Bernhard Schönenberger, and Arnold Brossi

*Section of Medical Chemistry, Laboratory of Analytical Chemistry, NIDDK, National Institute of Health, Bethesda, MD 20982, U.S.A.

Abstract

A new approach to 1-oxo-2,3,4,5-tetrahydro-1H-2-benzazepines is described, the key step being the rutheniun catalyzed oxidative cleavage of 1-methylene-2-benzazepine 5 obtained by N-acetylation of the Bischler-Napieralski cyclization product of N-acetyl-3-(3’,4’.5’-trimethoxyphenyl)-propylamine (3). Aromatic bromination instead of benzylic oxidation took place upon irradiation of the 1-oxo-2-benzazepine 8 with visible light in the presence of CaCO3 and NBS.