Beilstein J. Org. Chem.2014,10, 2377–2387, doi:10.3762/bjoc.10.248
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Keywords: 1,3-dipolar cycloadditions; multicomponent; one-pot three-component reactions; pyrrolo[1,2-a]benzimidazole; pyrrolo[1,2-a]quinoxalin-4-one; Introduction
The pyrrolo[1,2-a]quinoxaline system has significant biological activities and is a subject fo constant interest. This skeleton is a
procedure towards pyrrolo[1,2-a]quinoxalin-4-ones and pyrrolo[1,2-a]benzimidazoles and we describe the influence of reaction conditions on the ratio of the two final reaction products. We developed also a selective one-pot three-component synthetic pathway towards pyrrolo[1,2-a]quinoxalin-4-one derivatives
-ones 4b,e only in some cases (Scheme 1, Table 1). All reactions have been performed by mixing the starting components at room temperature in 1,2-epoxybutane and heating the reaction mixture for 24 hours at reflux temperature. Pyrrolo[1,2-a]quinoxalin-4-one derivatives 4 were isolated from the reaction
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Graphical Abstract
Scheme 1:
Synthesis of pyrrolo[1,2-a]quinoxalin-4-ones 4 and pyrrolo[1,2-a]benzimidazoles 5.