Synthesis and antimicrobial evaluation of some 1,2,4-triazole, 1,3,4-oxa(thia)diazole, and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives

3-Methyl-2-benzofurancarboxylic acid hydrazide (2) reacts with carbon disulfide and potassium hydroxide to give the corresponding potassium carbodithioate salt 3. Treatment of the latter salt with hydrochloric acid, hydrazine hydrate, and with phenacyl bromide afforded the corresponding 1, 3,4-oxadiazole-5-thione 4, 4-amino-1,2,4-triazole-5-thione 5, and thiazolidine-2-thione 9 derivatives, respectively. The reaction of either 1,3,4-oxadiazole-5-thione 4 or 4-amino-1,2,4-triazole-5-thione 5 with phenacyl bromide resulted in the formation of 1,2,4-triazolo[3, 4-b]-1,3,4-thiadiazine derivative 8. Treatment of compounds 3 or 4 with hydrazonoyl halides 10a-d furnished the same 1,3,4-thiadiazol-2-ylidene derivatives 11a-d. The 7-aryllhydrazono-1,2,4-triazolo[3,4-b]-1, 3,4-thiadiazine derivatives 12a-d were obtained either by treatment of 4-amino-1,2,4-triazole-5-thione 5 with hydrazonol halides 10a-d or by coupling of the 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivative 8 with diazonium salts. (c) 2005 Wiley Periodicals, Inc.