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Open AccessArticle

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

1
Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno 612 42, Czech Republic
2
Department of Chemistry, Faculty of Science, Centre for Syntheses at Sustainable Conditions and Their Management, Masaryk University, Brno 625 00, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Romano V. A. Orru
Molecules 2019, 24(19), 3586; https://doi.org/10.3390/molecules24193586
Received: 20 September 2019 / Revised: 30 September 2019 / Accepted: 3 October 2019 / Published: 5 October 2019
(This article belongs to the Special Issue Advances in One-Pot Reaction)
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. View Full-Text
Keywords: 1,3,5-triazine; supported Cu(I) catalyst; Ullmann reaction; one-pot synthesis 1,3,5-triazine; supported Cu(I) catalyst; Ullmann reaction; one-pot synthesis
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MDPI and ACS Style

Havránková, E.; Csöllei, J.; Pazdera, P. 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. Molecules 2019, 24, 3586.

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