Reactivity of N-(4-Nitrophenyl)propionohydrazonoyl Bromide. Synthesis and Antimicrobial Study of Thiadiazoles and 4,6-Dithia-1,2,9-triazaspiro-[4.4]-non-2-en-8-ones

Abstract

Treatment of thioanilides with N-(4-nitrophenyl)propionohydrazonoyl bromide in refluxing chloroform in the presence of triethylamine gave thiadiazoles. Stirring of 2-((methylthio)carbonthioyl)hydrazonoes with hydrazonoyl bromide in ethanol in the presence of triethylamine at room temperature afforded the corresponding thiadiazole derivatives. Also, reaction of 5-arylidene-3-phenyl-2-thioxothiazolidin-4-ones and hydrazonoyl bromide in chloroform in the presence of triethylamine at reflux to yield the corresponding 4,6-dithia-1,2,9-triazaspiro[4.4]non-2-en-8-one derivatives. The structures of the latter new products were identified by elemental analysis and spectral data. Antimicrobial studies were performed against all synthesized compounds. Compounds 15Bb, 15Be, and 18d were exhibited high antimicrobial activities against the tested microorganisms. The other compounds showed no activities.

Keywords:

• Hydrazonoyl bromide
• thioanilides
• thiadiazoles
• thiosemicarbazide
• methyl hydrazinecarbodithioate
• antimicrobial activity