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

doi:10.1002/ejoc.201402723

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 journal › Article › peer-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 language	English
Pages (from-to)	6390-6393
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2014
Issue number	29
DOIs	https://doi.org/10.1002/ejoc.201402723
Publication status	Published - Oct 1 2014
Externally published	Yes

Keywords

Domino reactions
Multicomponent reactions
Nitrogen heterocycles
Synthetic methods

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry

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Assembly of a 1H-Pyrrol-2(5H)-one core through a cascade Ugi reaction/5-endo-dig carbocyclization/retro-claisen fragmentation process. / Peshkov, Anatoly A.; Peshkov, Vsevolod A.; Li, Zhenghua; Pereshivko, Olga P.; Van Der Eycken, Erik V.

In: European Journal of Organic Chemistry, Vol. 2014, No. 29, 01.10.2014, p. 6390-6393.

Research output: Contribution to journal › Article › peer-review

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AU - Pereshivko, Olga P.

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