REACTIONS WITH HYDRAZONOYL HALIDES XVII^[l]. SYNTHESIS AND REACTIONS OF 1-BROMO-2-[4-(N-PIPERIDINO-SULFONYL)PHENYL]ETHANEDIONE-1-ARYLHYDRAZONE

Abstract

The reaction of sulfamidohydrazonoyl bromide 3 with nucleophiles led to displacement of the bromide. Treatment of 3 with potassium thiocyanate or potassium selenocyanate gave 2-imino-1,3,4-thiadiazolines 5 and 2-iminoselenadiazolines 6 respectively. Reaction of 3 with thiourea and phenylthiourea yielded the thiazole derivatives 15 and 16, while dithioesters 26(or 27) reacts with 3 to afford 2,3-dihydro-1,3,4-thiadiazoles 30–32.

Key Words:

• Hydrazonoyl halides
• 2,3-Dihydro-1,3,4-thiadiazole
• 2,3-Dihydro-1,3,4-selenadiazole
• dithioate esters: Nitrile imides