Synthesis of heterocycles. Part VII Synthesis and antimicrobial activity of some 7H‐s‐triazolo[3,4‐b][1,3,4]thiadiazine and s‐triazolo[3,4‐b][1,3,4]thiadiazole derivatives

Abstract

The cyclization of 4‐amino‐5‐aryl‐3‐cyanomethylthio‐1,2,4‐triazoles II in the presence of concentrated sulfuric acid yields 7H‐6‐amino‐s‐triazolo[3,4‐b][1,3,4]thiadiazines III. Cyclization of 4‐amino‐5‐aryl‐1,2,4‐tria‐zole‐3‐thiones I with phenacyl chloride yields 7H‐3‐aryl‐6‐phenyl‐s‐triazolo[3,4‐b][1,3,4]thiadiazines IV. Similarly, compounds I condensed with cyanogen bromide, phenyl isothiocyanate and carbon disulfide to give the corresponding cyclized products 6‐amino‐3‐aryl‐s‐triazolo[3,4‐b][1,3,4]thiadiazoles V, 3‐aryl‐6‐phenyl‐amino‐s‐triazolo[3,4‐b][1,3,4]thiadiazoles VI and 3‐aryl‐striazolo[3,4‐b][1,3,4]thiadiazol‐6(5H)thiones VII, respectively. Also in the presence of phosphoryl chloride, compounds I underwent cyclization with monocarbo‐xylic acids and oxalic acid to 3,6‐diaryl‐s‐triazolo[3,4‐b][1,3,4]thiadiazole VIII and 6,6′‐bis(3‐aryl‐s‐triazolo‐[3,4‐b][1,3,4]thiadiazoles) IX. The above compounds were screened for their antimicrobial activity.

Synthesis and properties of N-aminoazolinethiones and N-aminoazinethiones 2. Reactions

“…The triazoles XII react with carbon disulfide in alcoholic alkali to give the thiones LXVI (60-70% yield) [78,79,84,88,89]. Compound LXVII was prepared analogously from 3-amino-quinazoline-2-thione [87].…”

Potentiometric Determination of Pharmaceutically Important Nimesulide in Non-Aqueous Medium

“…Some of the present day drugs such as ribavirin (antiviral agent), rizatriptan (antimigraine agent), alprazolam (anxiolytic agent), fluconazole and itraconazole (antifungal agents) are the best examples for potent molecules possessing triazole nucleus [5][6][7] . Many literatures have shown that Mannich bases possess potent biological activities such as antibacterial, antifungal, anti-inflammatory, antimalarial and pesticide properties [8][9][10][11] . Few Mannich bases derived from 1,2,4-triazoles carrying N-methylpiperzine substituent were biologically active 12,13 .…”

1H and13C NMR spectroscopy of 6-aryl-substituted 3-[5-methyl-1-(4-methylphenyl)-1,2,3-triazol-4-yl]-s-triazolo[3,4-b]-1,3,4-thiadiazoles

“…In particular, s-triazolo [3,4-b]-1,3,4-thiadiazole derivatives are of interest because of their broad range of biological activities such as antifungal, 1 antibacterial, 2 hypotensive and CNS depressant 3 activities. The 1,2,3-triazole derivatives form an interesting class of compounds, which are widely used in medicine, agriculture and industry.…”