Palladium-Catalyzed Tandem Regioselective Oxidative Coupling from Indoles and Maleimides: One-Pot Synthesis of Indolopyrrolocarbazoles and Related Indolylmaleimides

Org Lett. 2016 Jan 15;18(2):152-5. doi: 10.1021/acs.orglett.5b02944. Epub 2015 Dec 28.

Abstract

An efficient Pd(II)-catalyzed approach for the direct synthesis of indolo[3,2-a]pyrrolo[3,4-c]carbazole-6,8-diones has been developed from both free and protected (NH) indoles and maleimides via a regioselective tandem oxidative coupling reaction. The yields are moderate to excellent. In addition, 2-substituted indoles are suitable substrates in this protocol, leading to the formation of indolylmaleimides. The present methodology provides a concise route to highly functionalized indolopyrrolocarbazole derivatives.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Catalysis
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Indoles / chemical synthesis*
  • Indoles / chemistry
  • Maleimides / chemical synthesis
  • Maleimides / chemistry*
  • Molecular Structure
  • Oxidative Coupling
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Carbazoles
  • Heterocyclic Compounds, 4 or More Rings
  • Indoles
  • Maleimides
  • Palladium