Synthesis of 5-(1,2,3-Triazol-4-yl)-1,3,4-Oxa(thia) diazol-2-Amines as Antimicrobial Agents

Abstract

N EFFICIENT method for the synthesis of new 1,2,3-triazol-4-yl-1,3,4-oxadiazol-2-amines (4a-c) from phenyliso-thiocyanate and 1,2,3-triazolyl-4-hydrazides (3a-c) through cyclo-desulfurization in the presence of sodium acetate is reported. Also, cyclization of 3a-c with concentrated H 2 SO 4 afforded the corresponding triazol-4-ylthiadiazoles)6a-c(. The new products were screened for their antimicrobial activities, and compounds; 4a-c showed excellent antimicrobial activities compared with the reference drugs. Also, the minimum inhibitory concentration (MIC) against the tested organisms was determined in which, compounds 2c and 4a showed the lowest MIC.

4-((5-(1-(4-Fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid: unexpected synthesis, structure elucidation and antimicrobial activity

“…The chemical shift (d) was reported in ppm and the coupling constant (J) was reported in Hz. Compounds 1 [22] and 3 [18] were prepared based on literature procedures. The Supplemental Materials contain the FTIR, 1 H, 13 C NMR spectra (Figures S1-S3), and bond lengths and angles for compound 4 (Table S1).…”

“…Here, we report the unexpected synthesis of 4-((5-(1-(4-Fluorophenyl)-5-methyl-1H-1,2,3-triazol-4-yl)-1,3,4-thiadiazol-2-yl)amino)benzenesulfonic acid using a simple procedure, in continuation of our long-term interest in the synthesis of bioactive molecules. [14][15][16][17] Results and discussion Chemistry Abdel-Wahab et al [18] have reported the synthesis of 2- The crystal structure comprises two independent molecules (M1 and M2) of 4 and two disordered ether solvent molecules (Figure 1). The molecule of 4 includes four rings (A D), namely; an aryl (M1A: C1 C6 and M2A: C18 C23), a triazolyl (M1B: C7, C8, N1 N3, and M2B: C24, C25, N7 N9), a thiadiazolyl (M1C: C10, C11, N4, N5, S1 and M2C: C27, C28, N10, N11, S3), and a second aryl (M1D: C12 C17, S2 and M2D: C29 C34) rings.…”