Synthesis, characterisation and antimicrobial activity of thiazole, bisthiazole, pyridone and bispyridone derivatives

Abstract

N-cyclohexyl-2-cyano-acetamide was reacted with phenyl isothiocyanates and sulfur to give thiazolidine and bisthiazolidine derivatives. Treatment of N-cyclohexyl-2-cyanoacetamide with phenyl isothiocyanate and KOH followed by in situ heterocyclisation with a-halo compounds gave thiazole derivatives. Treatment of N-cyclohexyl-2-cyanoacetamides with cinnamonitriles gave pyridone and bispyridone derivatives. N-cyclohexyl-2-cyanoacetamide coupled smoothly with benzene-diazonium chloride in pyridine. Cyclocondensation of N-cyclohexyl-2-cyanoacetamide with acetylacetone gave 1,1'-(ethane-1,2-diyl) bis(4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile). Ternary condensation of N-cyclohexyl-2-cyanoacetamide, malononitrile and acetaldehyde gave a bispyridone derivative. Some of the new compounds were tested against bacteria and some fungi.