A set of novel series of 1,3,4-thiadiazolyl-sulfanyl-4,5-dihydropyridazin-3(2H)-ones with anticipated antimicrobial activity has been synthesized. The synthetic protocol of the targeted compounds was accomplished by treating β-aroylacrylic acid 1 with 5-amino-1,3,4-thiadiazole-2-thiol (2) to afford the thia-Michael adduct 3. Afterwards, the obtained thia-Michael adduct 3 was cyclized to 4,5-dihydropyridazin-3(2H)-ones 4a-d and the non-cyclized product hydrazone 5 by using different hydrazines. Moreover, adduct 3 was reacted with esters like diethyl malonate and ethyl acetoacetate affording 1,3,4-thiadiazolobutanamides 6a, b. Furthermore, the concurrent reaction of later butamides 6a, b with the hydrazine derivatives furnished thiadiazolopyridazin-3(2H)-ones 7a-d, 8, and butanoic acid 9.
Keywords: 6-aryl-4,5-dihydropyridazin-3(2H)-one; antimicrobial activity; hydrazone; thia-Michael addition; thiadiazolopyridazin-3(2H)-one; β-aroylacrylic acid.