Ionic Liquid Effect over the Biginelli Reaction under Homogeneous and Heterogeneous Catalysis

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Bronsted. and Lewis acid catalysts, with ionic tags under homogeneous, and heterogeneous conditions' have,been tested to perform the Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-one (DHPMs). Metal-containing ionic liquids were evaluated as the catalysts with reasonable results (homogeneous systems). Heterogeneous catalysts (zeolite beta and H3PW12O40 supported zeolite beta) have been tested, as Well, with good to excellent results. The use of a functionalized acid ionic liquid with a heteropolyacid in the anion moiety (homogeneous system) gave the best results using no excess of the three reagents. The preferred Mechanistic pathway was investigated by electrospray ionization (tandem) mass spectrometry in both positive and negative ion modes with very elucidative results. The ionic liquid effect and its origin were also investigated using mass spectrometry and DFT calculations.3714201430Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)FINEP-MCTFINATECFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)FAPDFDPP-UnBANP-PETROBRASCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP