The use of benzil to obtain functionalized N-heterocycles

Abstract

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. ©2008 Sociedade Brasileira de Química.