Differentiating alkyne reactivity in the post-Ugi transformations: Access to polycyclic indole-fused frameworks

Chao Liu, Gaigai Wang, Yingchun Wang, Kristof Van Hecke, Olga P. Pereshivko, Vsevolod A. Peshkov

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The Ugi adducts prepared from propiolic acids, propargylamines, indole-2-carbaldehydes, and isocyanides were utilized to assemble polycyclic indole-fused frameworks via two consecutive carbocyclizations involving triple bonds. First, the peptidyl position of Ugi adduct underwent potassium carbonate-mediated cyclization onto the triple bond derived from propiolic acid. Then, the position 3 of indole core engaged into gold-catalyzed cyclization onto the propargylamine-originated alkyne, completing the construction of polycyclic core.

Original languageEnglish
Pages (from-to)1823-1827
Number of pages5
JournalTetrahedron Letters
Volume59
Issue number19
DOIs
Publication statusPublished - May 9 2018
Externally publishedYes

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Alkynes
Cyclization
Cyanides
Gold
indole
propargylamine
propiolic acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Differentiating alkyne reactivity in the post-Ugi transformations : Access to polycyclic indole-fused frameworks. / Liu, Chao; Wang, Gaigai; Wang, Yingchun; Van Hecke, Kristof; Pereshivko, Olga P.; Peshkov, Vsevolod A.

In: Tetrahedron Letters, Vol. 59, No. 19, 09.05.2018, p. 1823-1827.

Research output: Contribution to journalArticle

Liu, Chao ; Wang, Gaigai ; Wang, Yingchun ; Van Hecke, Kristof ; Pereshivko, Olga P. ; Peshkov, Vsevolod A. / Differentiating alkyne reactivity in the post-Ugi transformations : Access to polycyclic indole-fused frameworks. In: Tetrahedron Letters. 2018 ; Vol. 59, No. 19. pp. 1823-1827.
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