Silver(I) Triflate-Catalyzed Protocol for the Post-Ugi Synthesis of Spiroindolines

Manzoor Zaman, Muhammad Hasan, Anatoly A. Peshkov, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko, Vsevolod A. Peshkov

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A silver(I) triflate-catalyzed protocol for the post-Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole-3-carbaldehyde-derived Ugi adducts obtained using anilines and 3-aryl propiolic acids. Thus, it is complementary to the previous cationic gold-catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3-alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel-Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four-component Ugi reaction into a two-step one-pot transformation. (Figure presented.).

Original languageEnglish
Pages (from-to)261-268
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number1
DOIs
Publication statusPublished - Jan 7 2020

Keywords

  • Domino reactions
  • Multicomponent reactions
  • Nitrogen heterocycles
  • Silver catalysis
  • Spiro compounds

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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