Studies in azole chemistry. Part I. Syntheses and reactions of some imidazole 3-oxides

Abstract

The syntheses are described of 1-benzyl-5-methyl-, 1-benzyl-4,5-dimethyl-, and 1-benzyl-5-hydroxymethyl-4-methyl-imidazole 3-oxide. The first two are deoxygenated by phosphorus trichloride, deoxygenated and chlorinated at C-2 by phosphoryl chloride, and take part in 1,3-dipolar addition reactions. By quaternisation and reaction with cyanide they give 2-cyanoimidazoles.