Antioxidant, Antifungal activity and Isomerisation: Synthesis of 1,2,3,5- thiatriazines

Abstract

Synthesis of thiatriazines having hetero atoms different positions has been reported in the literature. The cycloaddition of diazoazoles with acylisothiocyanates has been found to result in the formation of a 1,2,3,5thiatriazine ring. Recently the synthetic applications of Nphenyl-S-chloroisothiocarbamoyl chloride have been investigated. Series of new heterocyclic compounds 2H-4-(pyrid-4yl)-5-arylidene / alkylidene-amino-6-phenylimino-5,6-dihydro-1,2,3,5-thiatriazine (8a-f) have been synthesized by the basification of 2H-4-(pyrid-4yl)-5arylidene / alkylideneamino-6-phenylimina-5,6dihydro-1,2,3,5-thiatriazine hydrochloride (7a-f). The later were synthesized by the interaction of 1-aryl / alkylidene-3-(pyrid-4y)dihydro formazan (5a-f) with N-phenyl-Schloroisothiocarbamoyl chloride. The synthesized compounds were further isomerised into 1 phenyl-4-(pyrid-4yl)-5-aryldene / alkyldene amino-6-thio-1,2,3,5tetrazines (9a-f) by using 5 % ethanolic sodium hydroxide. Compound (8) on benzalyation with excess 10 % sodium hydroxide and benzoyl chloride afforted corresponding benzoyl derivatives (10 a-f). The structures of newly synthesized compounds were confirmed on the basis of their elemental IR 1 H-NMR and mass spectral analysis. The title compounds were assayed for antioxidant activity compared with standard ascorbic acid and antifungal Activity.

Novel 6-aryl-7-alkyl/aryl-[1,2,4]triazolo[4,3-a][1,3,5]triazine-5(6H)-thiones, processes for their preparation, characterization and evaluation of their in vitro antioxidant activity

“…The 3-amino [1,2,4]triazole was reacted with orthoesters in the presence of acetic acid to afford the imidates (1) which has been described [14]. The reaction between N-triazol-3-yl imidates (1) with appropriate isothiocyanate under reflux of toluene leads to 6-aryl-7-alkyl/aryl- [1,2,4]triazolo [4,3-a] [1,3,5]triazine-5(6H)-thione (2a-i) (Scheme 1, Table 1). Scheme 1.…”

“…Scheme 1. Synthesis reaction of 6-aryl-7-alkyl/aryl- [1,2,4]triazolo [4,3-a][1,3,5]triazine-5(6H)thione (2a-i). The structure of the products (2a-i) was established with help of the spectral data.…”

“…6-Benzyl-7-methyl- [1,2,4]triazolo [4,3-a] 6-(Furan-2-ylmethyl)-7-methyl- [1,2,4]triazolo [4,3-a] [1,3,5] [1,2,4]triazolo [4,3-a] [1,3,5] [1,2,4]triazolo [4,3-a] [1,3,5] [1,2,4]triazolo [4,3-a] [1,3,5] [1,2,4]triazolo [4,3-a] [1,3,5]triazine-5(6H)-thione (2h). (205.2 mg, 54%); a yellowish needles solid; mp 270-272 °C; IR (FT-IR 200, ν (cm -1 )): 1270 (C=S), 1612 (C=N), 3580 (OH); 1 H NMR (300 MHz, DMSO-d6): δ 1.23 (t, 3H, 3 JHH = 8.7…”

“…Extensive research in the organic-medicinal chemistry field has led to the discovery of different classes of bioactive substances, most of being sulfur and nitrogen-containing heterocycles [1][2][3][4]. Heterocyclic compounds are present in various drugs, several natural products, some vitamins, biomolecules, and biologically active compounds such as anti-inflammatory [5], antitumour [6], antimalarial [7], antidepressant [8], anti-HIV [9], and antimicrobial [10] agents.…”

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A series of nine new 6-aryl-7-alkyl/aryl- [1,2,4]triazolo [4,3-a][1,3,5]triazine-5(6H)-thiones (2a-i) were synthesized by a reaction of N-triazol-3-yl imidates (1) with three different isothiocyanate derivatives (RNCS) in refluxing toluene. The structures of the final heterocyclic compounds were confirmed by 1 H-NMR, 13 C-NMR, FT-IR, elemental analysis, and mass spectral analysis.

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