Palladium-Catalyzed N-Arylation of 3-Functionalized 2-Amino-4,5-dimethylpyrroles

Abstract

A versatile class of 2-aminopyrroles containing various electron-withdrawing substituents at the 3-position have been N-arylated on the amine using a palladium-catalyzed cross-coupling reaction. Using this methodology, a pyrimidone-based tricyclic system has been prepared in just one step from a starting 2-aminopyrrole.

Keywords:

• 2-Aminopyrrole
• DPEphos
• N-arylation
• palladium-catalyzed
• pyrrolo[2,3-d]pyrido[1,2-a]pyrimidine
• xantphos

ACKNOWLEDGMENTS

We thank our department and the Pamplin College of Arts and Sciences for funding of this research.

Notes

^a Isolated yield of pure product after column chromatography.

^b Based on TLC comparison to an authentic sample.

^a Isolated yield of pure product after column chromatography.

^b Based on ¹H NMR of the partially purified product.