Letters in Organic Chemistry

Gwilherm Evano
Free University of Brussels
Brussels
Belgium

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Intramolecular Aromatic Substitutions of the Imidazol-5-yl Radical to form Tricyclic Imidazo[5,1-a] Heterocycles

Author(s): Mairead A. Clyne, Fawaz Aldabbagh.

Abstract:

Five, six and seven-membered intramolecular aromatic substitutions of imidazol-5-yl radicals are reported using both metal hydride/AIBN and photochemical conditions to give imidazo[5,1-a]isoindole, imidazo[5,1-a]isoquinoline and imidazo[5,1-a]benzazepine. Procedures for the synthesis of 5-bromo-(N-ω- phenylalkyl)imidazole radical precursors using 1,3-dibromo-5,5-dimethylhydantoin (dibromantin) and Nbromosuccinimide (NBS) are given.

Keywords: tributyltin hydride, radical cyclizations, photochemistry, imidazoles, Brominations

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Article Details

VOLUME: 3
ISSUE: 7
Year: 2006
Page: [510 - 513]
Pages: 4
DOI: 10.2174/157017806778341960
Price: $58