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

Organic & Biomolecular Chemistry Pub Date: 2013-06-11 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.

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