Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: Access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones

Olga P. Pereshivko, Vsevolod A. Peshkov, Anatoly A. Peshkov, Jeroen Jacobs, Luc Van Meervelt, Erik V. Van Der Eycken

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

Cationic gold-catalyzed cycloisomerizations of propargylureas, derived in situ from secondary propargylamines and aryl or alkyl isocyanates, have been studied. The reaction outcome was found to be different from what was previously observed for the tosyl isocyanate-derived ureas in terms of both regio- and chemoselectivity. As a result, the current protocol offers efficient access to the 3,4-dihydropyrimidin-2(1H)-one core through the 6-endo-dig N-cyclization.

Original languageEnglish
Pages (from-to)1741-1750
Number of pages10
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number11
DOIs
Publication statusPublished - Mar 21 2014

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

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