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.

• Klíčová slova
• 1,3,5-triazine, Ullmann reaction, one-pot synthesis, supported Cu(I) catalyst,
• MeSH
• katalýza MeSH
• měď chemie   MeSH
• molekulární struktura MeSH
• poréznost MeSH
• triaziny chemická syntéza   chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• srovnávací studie MeSH
• Názvy látek
• měď MeSH
• triaziny MeSH

A method for preparation of a new stable Cu(I) catalyst supported on weakly acidic polyacrylate resin without additional stabilizing ligands is described. A simple and efficient methodology for Ullmann Cu(I) catalyzed C-N cross coupling reactions using this original catalyst is reported. Coupling reactions of 4-chloropyridinium chloride with anilines containing electron donating (EDG) or electron withdrawing (EWG) groups, naphthalen-2-amine and piperazine, respectively, are successfully demonstrated.

• Klíčová slova
• C-N coupling, polymer solid support, recyclable green catalyst, supported Cu(I) catalyst,
• MeSH
• 2-naftylamin chemie   MeSH
• akrylové pryskyřice chemie   MeSH
• aniliny chemie   MeSH
• elektrony * MeSH
• katalýza MeSH
• koncentrace vodíkových iontů MeSH
• měď chemie   MeSH
• opakované použití vybavení MeSH
• piperazin MeSH
• piperaziny chemie   MeSH
• pyridinové sloučeniny chemická syntéza   MeSH
• technologie zelené chemie MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• 2-naftylamin MeSH
• akrylové pryskyřice MeSH
• aniliny MeSH
• měď MeSH
• piperazin MeSH
• piperaziny MeSH
• pyridinové sloučeniny MeSH