ISSN:
1434-193X
Keywords:
Heterocycles
;
NBS bromination
;
Selective bromination
;
Polybrominated thiazole
;
Structure elucidation
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
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