NITRILE SULFIDES. SYNTHESIS OF 2-(1,2,4-THIADIAZOLYL)BENZOATES AND 2-(1,2,4-THIADIAZOLYL)BENZONITRILES

Article abstract of DOI:10.1021/jo00317a024

1,3-Dipolar cycloadditions of aromatic nitrile sulfides to methyl o-cyanobenzoate and to phthalonitrile gave methyl 2-(3-aryl-1,2,4-thiadiazol-5-yl)benzoates 6a-c and 2-(3-phenyl-1,2,4-thiadiazol-5-yl)benzonitrile (7).Cycloaddition of 2-cyanobenzonitrile sulfide to aromatic nitriles gave 2-(5-aryl-1,2,4-thiadiazol-3-yl)benzonitriles 11a,b, which were converted to methyl 2-(5-aryl-1,2,4-thiadiazol-3-yl)benzoates 13a,b.Yields of the cycloadducts are increased by dilution of the reaction mixtures with a nonpolar solvent.