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Highly flexible and efficient syntheses of 1,2,3,5-substituted pyrroles starting from 2-propynyl- 1,3-dicarbonyl compounds and amines are presented. TFA catalyzed formation of the pyrroles is suggested to proceed through sequential amination of the carbonyl compounds followed by regioselective 5-exo-dig cyclization of the enaminone intermediate and aromatization.

arkivoc

TFA catalyzed sequential amination/annulation/aromatization reaction of 2-propynyl-1.3-dicarbonyl compounds with amines: A new one-pot approach to functionalized pyrroles