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

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

References

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14

Production of only 8a was observed without the use of 4 Å MS.