Journal of the Brazilian Chemical Society
versión impresa ISSN 0103-5053
versión On-line ISSN 1678-4790
BRAIBANTE, Mara E. F. et al. The use of benzil to obtain functionalized N-heterocycles. J. Braz. Chem. Soc. [online]. 2008, vol.19, n.5, pp.909-913. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532008000500015.
In this work, the reactivity of benzil was studied, employing C, N- and N, N-nucleophiles, such as ethyl(3-amino substituted) 2-butenoates 4a-c , (S, Z)-ethyl 3-(1-ethoxy-3-hydroxy-1-oxopropan-2-ylamino)but-2-enoate 6, semicarbazide 8 or thiosemicarbazide 10, to evaluate their electrophilic centers as building blocks for the synthesis of the polyfunctionalized heterocyclic compounds, resulting in pyrrolinone 5a-c, pyrrole 7, triazinone 9 and triazinethione 11. The employed benzil 3 was obtained by the oxidation of the benzoin under solvent free conditions in a comparative study between different protocols of oxidation, using the methodology under mild reaction conditions and supported reagent associated to the microwave irradiation, with good results and without aggressive reagents.
Palabras clave : solid support; benzil; N-heterocycles.