An organocatalytic highly efficient approach to the direct synthesis of substituted carbazoles in water

Org Biomol Chem. 2013 Dec 28;11(48):8410-8. doi: 10.1039/c3ob42034e. Epub 2013 Nov 5.

Abstract

A simple, mild, green, catalytic and general procedure for the direct synthesis of highly functionalized 1-methoxycarbonyl-2-aryl/alkyl-3-nitro-9H-carbazoles has been achieved in water medium via a one-pot domino Michael-Henry/aromatization reaction of methyl 2-(3-formyl-1H-indol-2-yl)acetates with aryl/alky-substituted β-nitroolefins under air using DABCO (30 mol%) as an organocatalyst. In addition, the bench scale synthesis can be performed without using toxic organic solvents and a biologically important new fused carbazole has been prepared.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Catalysis
  • Green Chemistry Technology
  • Piperazines / chemistry
  • Water / chemistry*

Substances

  • Carbazoles
  • Piperazines
  • Water
  • triethylenediamine