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Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts

An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to a-hydroxycarbonyl compound. Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been success fully carried out with 98% conversion and 83% global yield to the final product. 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.
- University of Cádiz Spain
- Universitat Politècnica de València Spain
- Cadi Ayyad University Morocco
Quinoxaline, Cascade process, Au/HT, 1,2-Phenylenediamine, Heterogeneous catalyst, 2-Methylquinoxaline, QUIMICA ORGANICA, Au/CeO2, Diol, Biomass
Quinoxaline, Cascade process, Au/HT, 1,2-Phenylenediamine, Heterogeneous catalyst, 2-Methylquinoxaline, QUIMICA ORGANICA, Au/CeO2, Diol, Biomass
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