Jump to main content
Jump to site search

Issue 2, 2006
Previous Article Next Article

Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH

Author affiliations

Abstract

Six-membered photochemical cyclisations of 2-iodo-N-(2-arylethyl)imidazoles proceeded regioselectively in higher yields than the equivalent tin hydride-mediated reactions. The decrease in yield of cyclisation products, 5,6-dihydroimidazo[2,1-a]isoquinolines containing strongly deactivating substituents on the aryl ring confirmed the electrophilic nature of the σ-imidazol-2-yl radicals. The seven-membered cyclisation was only successful under photochemical conditions, as radical reduction occurred with tin hydride. Nitration of 5,6-dihydroimidazo[2,1-a]isoquinoline with nitric/sulfuric acid occurred at the 2- and 8-positions.

Graphical abstract: Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH

Back to tab navigation

Publication details

The article was received on 12 Sep 2005, accepted on 10 Nov 2005 and first published on 05 Dec 2005


Article type: Paper
DOI: 10.1039/B512729G
Citation: Org. Biomol. Chem., 2006,4, 268-277
  •   Request permissions

    Photochemical intramolecular aromatic substitutions of the imidazol-2-yl radical are superior to those mediated by Bu3SnH

    M. A. Clyne and F. Aldabbagh, Org. Biomol. Chem., 2006, 4, 268
    DOI: 10.1039/B512729G

Search articles by author

Spotlight

Advertisements