Comparative reactivity of 3-methyl-5-phenylisoxazole and 3-methyl-5-phenylisothiazole against electrophilic compounds |
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Authors: | Angel Alberola Luis Calvo Ma Teresa Rodríguez Rodríguez Ma Carmen Saudo |
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Institution: | Angel Alberola,Luis Calvo,Ma Teresa Rodríguez Rodríguez,Ma Carmen Sañudo |
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Abstract: | 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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