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

Mairead   A.   Clyne; Fawaz      Aldabbagh

doi:10.2174/157017806778341960

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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Letters in Organic Chemistry

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

Volume: 3 Issue: 7

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

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

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.

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Clyne A. Mairead and Aldabbagh Fawaz, Intramolecular Aromatic Substitutions of the Imidazol-5-yl Radical to form Tricyclic Imidazo[5,1-a] Heterocycles, Letters in Organic Chemistry 2006; 3 (7) . https://dx.doi.org/10.2174/157017806778341960