Gold Catalysis Opens Up a New Route for the Synthesis of Benzimidazoylquinoxaline Derivatives from Biomass Derived Products (Glycerol)

Process intensification by using well-defined solid catalysts able to perform one-pot multistep reactions is one of the open fronts in heterogeneous catalysis. This is even more relevant if new, more efficient synthesis routes are open. Herein, a gold catalyst was used to synthesize benzimidazoylquinoxalines compounds by two efficient and selective novel methods in a multistep one-pot methodology. The first method involved the synthesis of benzimidazoylquinoxaline compounds with the same substituents in both heterocycles through oxidation– cyclization of glycerol with o-phenylenediamine derivatives, whereas the second one allowed the synthesis of benzimidazoylquinoxalines compounds with different substituents in each aromatic ring through coupling of o-phenylenediamine derivatives with glyceraldehyde in a first stage to produce the benzimidazol compound as an intermediate, followed by an oxidation–cyclization with another o-phenylenediamine compound in a second stage. Both stages were performed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) as the catalyst and air as the oxidant, in absence of any homogeneous reagent. A reaction mechanism has been proposed.The authors wish to acknowledge the Spanish Ministry of Education and Science for the financial support in the projects Consolider-Ingenio 2010 and CTQ-2011-27550. Generalitat Valenciana is also thanked for funding through the Prometeo program. S. M. S thanks Spanish Ministry of Education and Science for FPI fellowships. The authors also thank to the Severo Ochoa program of the Spanish Ministry of Education and Science.Climent Olmedo, MJ.; Corma Canós, A.; Iborra Chornet, S.; Martínez Silvestre, S. (2013). Gold Catalysis Opens Up a New Route for the Synthesis of Benzimidazoylquinoxaline Derivatives from Biomass Derived Products (Glycerol). ChemCatChem. 5(12):3866-3874. https://doi.org/10.1002/cctc.20130041638663874512Bozell, J. J., & Petersen, G. R. (2010). 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