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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

2012; Elsevier BV; Volume: 292; Linguagem: Inglês

10.1016/j.jcat.2012.05.002

1090-2694

María J. Climent, Avelino Corma, Juan Carlos Hernández‐Garrido, Ana B. Hungría, Sara Iborra, Sergio Martínez‐Silvestre,

Multicomponent Synthesis of Heterocycles

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 α-hydroxycarbonyl compound. Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product.