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COMPARATIVE REACTIVITY OF 3-METHYL-5-PHENYLISOXAZOLE AND 3-METHYL-5-PHENYLISOTHIAZOLE AGAINST ELECTROPHILIC COMPOUNDS
A comparative study of reactions of 3-methyl-5-phenylisoxazole and 3-methyl-5-phenylisothiazole with electrophilic compounds in the presence of n-BuLi, LICA or LICA-TMEDA is reported. By using LICA-TMEDA, regioselective reactions of the heterocyclic compounds at the C-3 methyl group are obtained. With n-BuLi or LICA and the isoxazole derivative a product mixture at the C-4 position and the C-3 methyl group is found. In the case of isothiazole compound, only with methyl iodide and n-BuLi, the dialkylated product at both positions is formed.
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Reference:
Isothiazole – Wikipedia,
,Isothiazole – ScienceDirect.com