Journal of Organic Chemistry p. 771 - 775 (1981)
Update date:2022-08-04
Topics:
Howe, Robert K.
Shelton, Becky R.
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.
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