✦ LIBER ✦

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

✍ Scribed by Florence Szydlo; Bruno Andrioletti; Eric Rose; Carine Duhayon

Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 177 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.04.028

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✦ Synopsis

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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