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

Fawaz Aldabbagh; Mairéad A. Clyne

doi:10.2174/157017806778341960

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

Fawaz Aldabbagh
, Mairéad A. Clyne

National University of Ireland

Research output: Contribution to journal › Article › peer-review

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 N-bromosuccinimide (NBS) are given.

Original language	English
Pages (from-to)	510-513
Number of pages	4
Journal	Letters in Organic Chemistry
Volume	3
Issue number	7
DOIs	https://doi.org/10.2174/157017806778341960
Publication status	Published - 2006
Externally published	Yes

Keywords

Brominations
Imidazoles
Photochemistry
Radical cyclizations
Tributyltin hydride

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10.2174/157017806778341960Licence: Other

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

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 N-bromosuccinimide (NBS) are given.",

keywords = "Brominations, Imidazoles, Photochemistry, Radical cyclizations, Tributyltin hydride",

author = "Fawaz Aldabbagh and Clyne, \{Mair{\'e}ad A.\}",

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doi = "10.2174/157017806778341960",

language = "English",

volume = "3",

pages = "510--513",

journal = "Letters in Organic Chemistry",

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publisher = "Bentham Science Publishers",

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T1 - Intramolecular aromatic substitutions of the imidazol-5-yl radical to form tricyclic imidazo[5,1-a] heterocycles

AU - Aldabbagh, Fawaz

AU - Clyne, Mairéad A.

PY - 2006

Y1 - 2006

N2 - 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 N-bromosuccinimide (NBS) are given.

AB - 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 N-bromosuccinimide (NBS) are given.

KW - Brominations

KW - Imidazoles

KW - Photochemistry

KW - Radical cyclizations

KW - Tributyltin hydride

U2 - 10.2174/157017806778341960

DO - 10.2174/157017806778341960

M3 - Article

AN - SCOPUS:33748881744

SN - 1570-1786

VL - 3

SP - 510

EP - 513

JO - Letters in Organic Chemistry

JF - Letters in Organic Chemistry

IS - 7

ER -

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

Abstract

Keywords

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