4,5-Dihydropyrrolo[1,2-a]quinoxalines and pyrrolo[1,2-a]quinoxalines have gained considerable interest in recent years owing to their wide variety of biological and pharmacological properties, including antiallergic, antiparacitic, antibacterial, antimalarial, antiulcer, antituberculosis and anticancer activities. Lewis acid catalyzed cyclizations have recently emerged as valuable tool in organic synthesis due to their high efficiency for new carbon-carbon and carbon-heteroatom bond formation. We have found that depending on the conditions, InCl3-catalyzed reactions of 1-(2-aminophenyl)pyrrole (1 ) with aldehydes and ketones 2  afford 4,5-dihydropyrrolo[1,2-a]quinoxalines 3  and pyrrolo[1,2-a]quinoxalines 4  in good to excellent yields. These reactions have also been utilized in the synthesis of complex heterocyclic systems by employing functionally substituted aldehydes and ketones. The scope, limitations and mechanism of these reactions will be discussed.

Synthesis of 4,5-dihydropyrrolo[1,2-a]quinoxaline and pyrrolo[1,2-a]quinoxaline derivatives

243rd National Meeting (2012)

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