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Communication | Regular issue | Vol 60, No. 1, 2003, pp.1-7
Published online, 15th November, 2002
DOI: 10.3987/COM-02-9598
Regioselective Synthesis of 1-Benzyl- and 1-Methyl-4-vinylimidazole and Their Reactions with N-Phenylmaleimide

Carl J. Lovely,* Hongwang Du, and H. V. Rasika Dias

*Department of Chemistry and Biochemistry, The University of Texas at Arlington, 502 Yates Street, Arlington, TX 76019, U. S. A.

Abstract

The regioselective synthesis of 1-benzyl- and 1-methyl-4-vinylimidazole from 4,5-diiodoimidazole is described. Their Diels-Alder reactions with N-phenylmaleimide provide a variety of adducts, including the anticipated enamine and the corresponding aromatized isomer. However, additional products including ene adducts, a bis Diels-Alder adduct and oxidation products were isolated.