Post-Ugi carbocyclization/fragmentation sequence for the synthesis of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones

Tran Thi Thu Trang, Anatoly A. Peshkov, Jeroen Jacobs, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van Der Eycken

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A two-step one-pot sequence, involving Ugi reaction followed by base-promoted carbocyclization accompanied by cleavage of the isocyanide-originated amide moiety, has been successfully elaborated in order to provide a fast access to 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. When the cyclizations were run under air atmosphere a subsequent oxidation occurred producing oxidized 7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones.

Original languageEnglish
Pages (from-to)2882-2886
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number22
DOIs
Publication statusPublished - May 27 2015
Externally publishedYes

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Cyclization
Cyanides
Atmosphere
Amides
Air
Oxidation

Keywords

  • 6,7-Dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones
  • Aerobic oxidation
  • Cyclization
  • Ugi reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Post-Ugi carbocyclization/fragmentation sequence for the synthesis of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. / Trang, Tran Thi Thu; Peshkov, Anatoly A.; Jacobs, Jeroen; Van Meervelt, Luc; Peshkov, Vsevolod A.; Van Der Eycken, Erik V.

In: Tetrahedron Letters, Vol. 56, No. 22, 27.05.2015, p. 2882-2886.

Research output: Contribution to journalArticle

Trang, Tran Thi Thu ; Peshkov, Anatoly A. ; Jacobs, Jeroen ; Van Meervelt, Luc ; Peshkov, Vsevolod A. ; Van Der Eycken, Erik V. / Post-Ugi carbocyclization/fragmentation sequence for the synthesis of 6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-ones. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 22. pp. 2882-2886.
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AU - Jacobs, Jeroen

AU - Van Meervelt, Luc

AU - Peshkov, Vsevolod A.

AU - Van Der Eycken, Erik V.

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