New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study

Abstract

An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The reaction times and yields were compared with traditional synthetic methods for synthesis of substituted 1,3,5-triazine derivatives via nucleophilic substitution of chlorine atoms in dichlorotriazinyl benzenesulfonamide. It was found that Ullmann-type reactions provide significantly shortened reaction times and, in some cases, also higher yields. Finally, trisubstituted s-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new s-triazine derivatives with potential biological activity were prepared and characterized.

Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

“…Starting monosubstituted dichlorotriazinyl (1-2) benzene sulfonamides were prepared as reported by Garaj et al [46]. Target compounds (3-32) were synthesized according to the methodology published by our team [47] by step-by-step nucleophilic substitution of chlorine atoms of 2,4,6-trichloro-1,3,5-triazine. The appropriate starting compound reacted with a nucleophile in the presence of anhydrous potassium carbonate in a molar ratio of 1:1:1.…”

Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido[2,1-c][1,2,4]triazolo[3,4-f][1,2,4]triazines

“…Aza-heterocycles are amongst the medications which have diverse uses in the market (Figure 1). Of this class, 1,2,4-triazines [7][8][9][10][11][12][13] and 1,2,4-triazoles [14][15][16][17][18][19][20][21], as well as pyrimidines [22,23], have been introduced in a renewed generation of medication. Due to our interest in these azines, their ligation, and modification, we revisited and continued upon our previous research projects [24][25][26][27][28][29][30] with this study.…”

New 1,3,5-Triazine Derivatives Incorporating Aminobenzenesulfonamide, Aminoalcohol, Piperazine, Chalcone or Stilbene Structural Motifs and Evaluation of Their Antioxidative Activity

“…Target compounds were prepared according to the methodology published in [15] by step by step nucleophile substitution of chlorine atoms in starting 2,4,6-trichloro-1,3,5-triazine. The appropriate starting compound reacted with a nucleophile and anhydrous potassium carbonate in a molar ratio 1:1:1.…”