A synthesis of 3-phenyl-1, 2, 3, 4-tetrahydroisoquinoline and 2-phenyl-1, 2, 4, 5-tetrahydro-3H-3-benzazepine via Pummerer-type cyclization: enhancing effect of …

T Saitoh, T Ichikawa, Y Horiguchi, J Toda…

Index: Toda, Jun; Ichikawa, Tsuyoshi; Saitoh, Toshiaki; Horiguchi, Yoshie; Sano, Takehiro Heterocycles, 2000 , vol. 53, # 9 p. 2009 - 2018

Full Text: HTML

Citation Number: 13

Abstract

A synthesis of 6, 7-dimethoxy-3-phenyl-1, 2, 3, 4-tetrahydroisoquinoline (14a) and 7, 8- dimethoxy-2-phenyl-1, 2, 4, 5-tetrahydro-3H-3-benzazepine (14b) was achieved via the cyclization of N-(3, 4-dimethoxyphenyl) methyl-1-phenyl-2-(phenylsulfinyl) ethylformamide (6a) and N-2-(3, 4-dimethoxyphenyl) ethyl-1-phenyl-2-(phenylsulfinyl)-ethylformamide (6b) using the Pummerer reaction as a key step, respectively. The Pummerer reaction of 6a, b ...