Assembly of a 1H-Pyrrol-2(5H)-one core through a cascade Ugi reaction/5-endo-dig carbocyclization/retro-claisen fragmentation process

Anatoly A. Peshkov, Vsevolod A. Peshkov, Zhenghua Li, Olga P. Pereshivko, Erik V. Van Der Eycken

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

A cascade transformation involving the Ugi reaction followed by 5-endo-dig carbocyclization and retro-Claisen fragmentation providing access to a 1H-pyrrol-2(5H)-one core is described. The operating protocol is very similar to the typical Ugi reaction settings, while the overall outcome results from the application of a 3-substituted propiolic acid and a phenylglyoxal as acid and aldehyde components, respectively. The utility of process is demonstrated through the synthesis of a small library of 5-oxo-2,5-dihydro-1H-pyrrole-2-carboxamides.

Original languageEnglish
Pages (from-to)6390-6393
Number of pages4
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number29
DOIs
Publication statusPublished - Oct 1 2014
Externally publishedYes

Keywords

  • Domino reactions
  • Multicomponent reactions
  • Nitrogen heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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