Synthesis of some new 3‐mercapto‐5‐substituted‐1,2,4‐triazine‐s‐triazoles for evaluation as antimicrobial agents

Abstract

The synthesis of several S‐ and N‐substituted derivatives of 5‐[(5,6‐diphenyl‐1,2,4‐triazin‐3‐yl)oxymethyl]‐s‐triazole‐3‐thiol, 2‐[(5,6‐diphenyl‐1,2,4‐triazin‐3‐yl)‐oxymethyl]‐5,6‐dihydrothiazolo‐[3,2‐b]‐s‐briazole, 2‐[(5,6‐diphenyl‐1, 2,4‐triazin‐3‐yl)oxymethyl]‐5H,6,7‐dihydro‐s‐triazolo‐[3,2‐b]‐1,3‐thiazine, 2‐[(5,6‐diphenyl‐1,2,4‐triazin‐3‐yl)oxymethyl]‐5,6‐dihydrothiazolo‐[3,2‐b]‐s‐triazol‐5‐one and 2‐[(5,6‐diphenyl‐1,2,4‐triazin‐3‐yl)oxymethyl]‐6‐phenylthiazolo‐[3,2‐b]‐s‐triazole is reported. All the novel compounds have been screened for antimicrobial activity and one of them showed noteworthy activity.

Regioselectivity in Reactions of Bis‐Hydrazonoyl Halides with Some Bifunctional Heterocycles

“…For ma tion of 6a rather than 7a is also in good agree ment with lit er a ture re ports which in di cate that re ac tion of 3-mercapto-5-aryl-1,2,4-triazoles with haloketones af forded 2-aryl-1,2,4triazolo[3,2-b]thiadiazole de riv a tives. [17][18][19][20] Re ac tion of 1 with 6-benzyl-2,3-dihydro-3-thioxo-1,2,4-triazin-5(4H)-one 2b in eth a nol in the pres ence of sodium ethoxide at room tem per a ture gave a mix ture of two prod ucts A and B in 72 and 10% yields, re spec tively. Both mass spec tra and el e men tal anal y ses of these two prod ucts A and B in di cated that their mo lec u lar for mu las are C 24 H 19 N 7 OS and C34H24N10O2, re spec tively.…”

One pot synthesis and reactions of novel 5-amino[1,3]thiazolo[3,2-b][1,2,4]triazoles

“…29 In the second route the thiazole ring is built onto a triazole ring via reaction of 3-mercapto-1,2,4-triazoles with α-haloketones 27,30 followed by cyclization of the thiomethylketone intermediate using PPA, 31 via reaction of 3-mercapto-1,2,4-triazoles with allyl bromide in the presence of aqueous sodium hydroxide solution, 32 or in a one step reaction using the mercaptotriazole, chloroacetic acid and aromatic aldehydes. [33][34][35][36][37][38][39] The third route involves chalcones reacting with bis(1H-1,2,4-triazolyl)sulfoxide to form thiazolo [3,2-b] [1,2,4]triazoles. 40 The present study is part of our program aimed at developing easy routes for the synthesis of fused heterocyclic compounds starting with cyano compounds containing active methylene groups.…”