Abstract
A general and simple method for the preparation of under explored 3-aryl-4-hydroxyfuroxans by nucleophilic substitution of the nitro group in 3-aryl-4-nitrofuroxans using NaOH in H2O-THF has been developed. The methylation of 3-aryl-4-hydroxyfuroxans was studied with various methylating reagents (CH2N2, MeI, (MeO)2SO2) which showed for the first time that 3-aryl-4-hydroxyfuroxans are prone to side-chain prototropic tautomerism. Furoxan derivatives of a novel type, N(5)-alkylation products (3-aryl-5-methyl-1,2,5-oxadiazol-4(2H)-one 2-oxides), were synthesized under mild conditions, along with regioselective formation of the O-alkylation products (3-aryl-4-methoxyfuroxans).
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