M. A. Hariri, O. Galley, F. Pautet
Apr 1, 1998
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0
Influential Citations
8
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Journal
European Journal of Organic Chemistry
Abstract
Radical bromination of 4,5-dimethylthiazole (1) was carried out using different stoichiometries of N-bromosuccinimide in the presence of 2,2′-azobisisobutyronitrile. Mono-, tri- and tetrabromo compounds 2, 5, and 6 were obtained in good yields with regioselectivity while the dibromo derivatives 3 and 4 were formed without any selectivity. Substitution at the thiazole ring occurred in the presence of silica gel or in the perfluoro ether FC-77 (C8F16O), affording the 2-bromothiazole 7. The order of reactivity observed was 5-Me > 4-Me > C-2. Structural assignment of compounds 2−7 was made by chemical correlations and NMR spectroscopy.