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

ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)


Volume 11, 10 Issues, 2014


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Letters in Organic Chemistry

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Editor-in-Chief:
Miguel Yus
Universidad de Alicante Apdo
Alicante
Spain


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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 and Fawaz Aldabbagh

Affiliation: Department of Chemistry,National University of Ireland, Galway, Ireland.

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 Number: 7
First Page: 510
Last Page: 513
Page Count: 4
DOI: 10.2174/157017806778341960
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