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      A Comparative Study on the Groebke-Blackburn-Bienaymé Three-Component Reaction Catalyzed by Rare Earth Triflates under Microwave Heating

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          Abstract

          Over the last twenty years, the Groebke-Blackburn-Bienaymé (GBB) reaction has been emerged as a powerful tool to access different nitrogen-based heterocycles as privileged scaffolds in medicinal chemistry. This multicomponent reaction is usually catalyzed by ordinary Brønsted or Lewis acid catalysts. Herein, we present a comparative study on the catalytic efficiencies of different rare earth triflates in GBB reactions under microwave heating, involving 2-aminopyridine or 2-aminothiazole, as aminoazole component, and different aldehydes and aliphatic isocyanides. The use of gadolinium(III) triflate as cheaper alternative catalyst for the most commonly used scandium(III) triflate was acknowledged for the first time, and a library of twenty three imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles could be obtained in good to excellent yields.

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          Author and article information

          Journal
          jbchs
          Journal of the Brazilian Chemical Society
          J. Braz. Chem. Soc.
          Sociedade Brasileira de Química (São Paulo, SP, Brazil )
          0103-5053
          1678-4790
          July 2020
          : 31
          : 7
          : 1434-1444
          Affiliations
          [1] Diadema São Paulo orgnameUniversidade Federal de São Paulo orgdiv1Instituto de Ciências Ambientais, Químicas e Farmacêuticas orgdiv2Departamento de Ciências Farmacêuticas Brazil
          Article
          S0103-50532020000701434 S0103-5053(20)03100701434
          10.21577/0103-5053.20200028
          0b4ee970-b14c-4935-89ac-d94eb450d82f

          This work is licensed under a Creative Commons Attribution 4.0 International License.

          History
          : 19 February 2020
          : 03 December 2019
          Page count
          Figures: 0, Tables: 0, Equations: 0, References: 77, Pages: 11
          Product

          SciELO Brazil

          Self URI: Full text available only in PDF format (EN)
          Categories
          Articles

          gadolinium(III) triflate,multicomponent reaction,rare earth triflate,catalysis,Groebke-Blackburn-Bienaymé

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