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

6 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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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