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Comparative reactivity of 3‐methyl‐5‐phenylisoxazole and 3‐methyl‐5‐phenylisothiazole against electrophilic compounds
Author(s) -
Alberola Angel,
Calvo Luis,
Rodríguez Rodríguez Ma Teresa,
Sañudo Ma Carmen
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320228
Subject(s) - chemistry , methyl iodide , regioselectivity , electrophile , reactivity (psychology) , isoxazole , isothiazole , methyl group , derivative (finance) , medicinal chemistry , stereochemistry , organic chemistry , group (periodic table) , catalysis , medicine , alternative medicine , pathology , financial economics , economics
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.