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
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...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/19/3586 |
| _version_ | 1819161176795250688 |
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| author | Eva Havránková Jozef Csöllei Pavel Pazdera |
| author_facet | Eva Havránková Jozef Csöllei Pavel Pazdera |
| author_sort | Eva Havránková |
| collection | DOAJ |
| description | 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 <i>s</i>-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new <i>s</i>-triazine derivatives with potential biological activity were prepared and characterized. |
| first_indexed | 2024-12-22T17:08:11Z |
| format | Article |
| id | doaj.art-79789a06215f4dee9e0ec8cbe6e7dca8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T17:08:11Z |
| publishDate | 2019-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-79789a06215f4dee9e0ec8cbe6e7dca82022-12-21T18:19:08ZengMDPI AGMolecules1420-30492019-10-012419358610.3390/molecules24193586molecules24193586New 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 StudyEva Havránková0Jozef Csöllei1Pavel Pazdera2Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno 612 42, Czech RepublicDepartment of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Brno 612 42, Czech RepublicDepartment of Chemistry, Faculty of Science, Centre for Syntheses at Sustainable Conditions and Their Management, Masaryk University, Brno 625 00, Czech RepublicAn 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 <i>s</i>-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new <i>s</i>-triazine derivatives with potential biological activity were prepared and characterized.https://www.mdpi.com/1420-3049/24/19/35861,3,5-triazinesupported cu(i) catalystullmann reactionone-pot synthesis |
| spellingShingle | Eva Havránková Jozef Csöllei Pavel Pazdera 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 1,3,5-triazine supported cu(i) catalyst ullmann reaction one-pot synthesis |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | 1,3,5-triazine supported cu(i) catalyst ullmann reaction one-pot synthesis |
| url | https://www.mdpi.com/1420-3049/24/19/3586 |
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