ON THE REACTIVITY OF HALO-1,3-AZOLES AND RELATED COMPOUNDS TOWARD AROMATIC SN2 SUBSTITUTION

Article abstract of DOI:10.3987/COM-90-5378

Nucleophilic addition-elimination reactions of 2-methylsulfonyl-1,3-azoles with active methylene compounds were investigated in order to compare the reactivity of substrates.The order of oxazole > thiazole >> N-methylimidazole in the reactivity was exhibited clearly.Furthermore, in oxazole and thiazole series, the predominant reactivity of the 2-position over the 4- and 5-positions was indicated on the reaction with the carbanions generated from active methylene compounds.