Efficient synthesis and solid state analysis of 3-(1H-pyrrol-2-yl)quinoxalin-2(1H)-one and 2-(1H-pyrrol-2-yl)-1H-benzo[d]imidazole from pyrrolo-2-ylglyoxyl acid |
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Authors: | Florence Szydlo Eric Rose |
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Affiliation: | a Université Pierre et Marie Curie-Paris 6, Laboratoire de chimie organique (UMR CNRS 7611), Institut de chimie moléculaire (FR 2769), 4 place Jussieu, case 181, 75252 Paris cedex 05, France b Université Pierre et Marie Curie-Paris 6, LCIM2—UMR CNRS 7071, 4 place Jussieu Bâtiment F, case 42, 75252 Paris cedex 05, France |
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Abstract: | The synthesis of new pyrrole-functionalized quinoxalines and benzimidazole is described. Our methodology involves the condensation between 2-oxo-2-(1H-pyrrol-2-yl)acetic acid and differently substituted 1,2-phenylene diamines. Depending on the substitution and on the reaction conditions, the synthesis leads to either the pyrrolyl-quinoxaline or -benzimidazole heterocycles. Further insights concerning the structural arrangement of the pyrrolyl-quinoxaline were obtained by solid state analysis, revealing an inverted pyrrole similar to that observed for 2,3-dipyrrolyl quinoxalines. This observation accounts for the fact that strong dipolar interactions or intermolecular H-bonds may govern the structural arrangement in the solid state. |
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Keywords: | Quinoxaline Benzimidazole Chromophore Heterocycles |
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