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Intramolecular aromatic substitutions of the imidazol-5-yl radical to form tricyclic imidazo[5,1-a] heterocycles

Clyne, Mairead
; 
Aldabbagh, Fawaz
Repository DOI
Publication Date
2006-07-01
Keywords
brominations, imidazoles, photochemistry, radical cyclizations, tributyltin hydride, mechanism, bu3snh
Type
Article
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Citation
Clyne, Mairead; Aldabbagh, Fawaz (2006). Intramolecular aromatic substitutions of the imidazol-5-yl radical to form tricyclic imidazo[5,1-a] heterocycles. Letters in Organic Chemistry 3 (7), 510-513
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-omega-phenylalkyl)imidazole radical precursors using 1.3-dibromo-5,5-dimethylhydantoin (dibromantin) and Nbromosuccinimide (NBS) are given.
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Publisher
Bentham Science Publishers Ltd.
Publisher DOI
10.2174/157017806778341960
Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (1)