Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

Olga P. Pereshivko, Vsevolod A. Peshkov, Denis S. Ermolatev, Sofie Van Hove, Kristof Van Hecke, Luc Van Meervelt, Erik V. Van Der Eycken

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA 2-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.

Original languageEnglish
Article numberZ21611SS
Pages (from-to)1587-1594
Number of pages8
JournalSynthesis
Issue number10
DOIs
Publication statusPublished - May 16 2011
Externally publishedYes

Keywords

  • 2-aminoimidazoles
  • ring closure
  • silver
  • spiro compounds
  • tandem reaction

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles'. Together they form a unique fingerprint.

Cite this