An efficient and facile access to highly functionalized pyrrole derivatives

Abstract

A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

Keywords

• azomethine ylides
• 1,3-dipolar cycloaddition
• one-pot synthesis
• polysubstituted pyrroles
• pyrrolo[3,4-c]pyrrole-1,3-diones