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 journalArticle

13 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

Fingerprint

Ketones
Silver
Amines
Derivatives
Copper
Alkynes
Guanidine
propargylamine
2-aminoimidazole

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Pereshivko, O. P., Peshkov, V. A., Ermolatev, D. S., Van Hove, S., Van Hecke, K., Van Meervelt, L., & Van Der Eycken, E. V. (2011). Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles. Synthesis, (10), 1587-1594. [Z21611SS]. https://doi.org/10.1055/s-0030-1260012

Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles. / Pereshivko, Olga P.; Peshkov, Vsevolod A.; Ermolatev, Denis S.; Van Hove, Sofie; Van Hecke, Kristof; Van Meervelt, Luc; Van Der Eycken, Erik V.

In: Synthesis, No. 10, Z21611SS, 16.05.2011, p. 1587-1594.

Research output: Contribution to journalArticle

Pereshivko, OP, Peshkov, VA, Ermolatev, DS, Van Hove, S, Van Hecke, K, Van Meervelt, L & Van Der Eycken, EV 2011, 'Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles', Synthesis, no. 10, Z21611SS, pp. 1587-1594. https://doi.org/10.1055/s-0030-1260012
Pereshivko OP, Peshkov VA, Ermolatev DS, Van Hove S, Van Hecke K, Van Meervelt L et al. Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles. Synthesis. 2011 May 16;(10):1587-1594. Z21611SS. https://doi.org/10.1055/s-0030-1260012
Pereshivko, Olga P. ; Peshkov, Vsevolod A. ; Ermolatev, Denis S. ; Van Hove, Sofie ; Van Hecke, Kristof ; Van Meervelt, Luc ; Van Der Eycken, Erik V. / Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles. In: Synthesis. 2011 ; No. 10. pp. 1587-1594.
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