Issue 32, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Apr 2013
Accepted
11 Jun 2013
First published
11 Jun 2013

Org. Biomol. Chem., 2013,11, 5254-5263

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

L. Xia and Y. R. Lee, Org. Biomol. Chem., 2013, 11, 5254 DOI: 10.1039/C3OB40791H

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