Efficient one-step synthesis of pyrrolo[3,4-c]quinoline-1,3-dione derivatives by organocatalytic cascade reactions of isatins and β-ketoamides

Org Biomol Chem. 2013 Aug 28;11(32):5254-63. doi: 10.1039/c3ob40791h.

Abstract

We describe an efficient one-step synthesis of pyrrolo[3,4-c]quinolinedione derivatives using ethylenediamine diacetate (EDDA)-catalyzed cascade reactions of isatins and β-ketoamides. It is the first direct conversion of isatins to pyrrolo[3,4-c]quinolinedione derivatives via C-N bond cleavage and isatin ring expansion. Furthermore, this reaction provides a one-step synthetic route for the production of biologically interesting complex molecules that are generally prepared using multi-step reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Catalysis
  • Edetic Acid / analogs & derivatives
  • Edetic Acid / chemistry
  • Isatin / chemistry*
  • Models, Molecular
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry

Substances

  • Amides
  • Pyrroles
  • Quinolines
  • EDDA
  • Isatin
  • Edetic Acid