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Development of an unexpected reaction pathway for the synthesis of 1,2,4-trisubstituted pyrrolo[1,2-a]quinoxalines through palladium-catalyzed cascade reactions
Authors:Ali Keivanloo  Atena Soozani  Mohammad Bakherad  Mahdi Mirzaee  Hadi Amiri Rudbari  Giuseppe Bruno
Institution:1. School of Chemistry, Shahrood University of Technology, Shahrood, 36199-95161, Iran;2. Department of Chemistry, University of Isfahan, 81746-73441, Iran;3. Department of Chemical Sciences, University of Messina, Via F. Stagno d’Alcontres 31, 98166, Messina, Italy
Abstract:1,2,4-trisubstituted pyrrolo1,2-a]quinoxalines are synthesized through the multi-component reaction of 3-substituted 2-chloroquinoxalines, propargyl bromide, and excess secondary amines in the presence of a palladium copper catalytic system. This one-pot process provides an unexpected synthesis of new trisubstituted pyrrolo1,2-a]quinoxalines by the introduction of two amine substituents onto the fused pyrrole rings in a single reaction procedure. The compounds formed are fully characterized by the analytical spectral data and X-ray analysis. A number of synthesized pyrrolo1,2-a]quinoxaline derivatives are also screened against the three bacterial strains Micrococcus luteus, Pseudomonas aeruginos, and Bacillus subtilis. According to the results obtained, compounds 3b, 3c, and 3e are active against M. luteus, compounds 3b and 3e are active against Ps. Aeruginos, and only compound 3f is active against all the three bacterial strains.
Keywords:Palladium-catalyzed  Cascade reaction  Multi-component reaction
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