4.6 Article

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

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 11, Issue 32, Pages 5254-5263

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c3ob40791h

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Funding

  1. Korean National Research Foundation (NRF)
  2. Korean Ministry of Education, Science, and Technology [2012M3A7B4049675]
  3. National Research Foundation of Korea [2012M3A7B4049675] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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We describe an efficient one-step synthesis of pyrrolo[3,4-c]quinolinedione derivatives using ethylenediamine diacetate (EDDA)-catalyzed cascade reactions of isatins and beta-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.

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