Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: a simple and direct synthesis of functionalized pyrroles

J Org Chem. 2010 Mar 5;75(5):1674-83. doi: 10.1021/jo902661y.

Abstract

A simple, convenient, and multicomponent coupling strategy for the synthesis of highly functionalized pyrroles catalyzed by iron(III) salts has been developed. This strategy demonstrated four-component coupling reactions of 1,3-dicarbonyl compounds, amines, aromatic aldehydes, and nitroalkanes without an inert atmosphere. This methodology provides an alternative approach for easy access of highly substituted pyrroles in moderate to very good yields using four simple and readily available building blocks via one-pot tandem reaction. Notably, this method is very cheap, straightforward, and environmentally friendly compared to the existing methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Alkanes / chemistry*
  • Amines / chemistry*
  • Catalysis
  • Cross-Linking Reagents / chemistry*
  • Crystallography, X-Ray
  • Iron / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitro Compounds
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Aldehydes
  • Alkanes
  • Amines
  • Cross-Linking Reagents
  • Nitro Compounds
  • Pyrroles
  • Iron