Facile Synthesis of 1-Methyl-1H-benzo[b]azepines
from 1-Methylquinolinium Iodides and Diazo(trimethylsilyl)methylmagnesium
Bromide

Mikio Morita; Yoshiyuki Hari; Toyohiko Aoyama

doi:10.1055/s-0030-1258306

PAPER

Facile Synthesis of 1-Methyl-1H-benzo[b]azepines from 1-Methylquinolinium Iodides and Diazo(trimethylsilyl)methylmagnesium Bromide

Mikio Morita^a, Yoshiyuki Hari*^b, Toyohiko Aoyama^a
^a Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho, Nagoya 467-8603, Japan
^b Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan
Fax: +81(6)68798201; e-Mail: hari@phs.osaka-u.ac.jp;

Abstract

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Abstract

The reaction of diazo(trimethylsilyl)methylmagnesium bromide, TMSC(MgBr)N₂, with 1-methylquinolinium iodides followed by sequential ring expansion using copper(I) chloride gives 1-methyl-3-(trimethylsilyl)-1H-benzo[b]azepines in moderate to good yields. Moreover, the trimethylsilyl group can be removed or converted into a hydroxy(phenyl)methyl group.

Key words

1H-benzo[b]azepines - diazo(trimethylsilyl)methylmagnesium bromide - quinolinium salts - ring expansion - (trimethylsilyl)diazomethane

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References

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