Titanium(IV) isopropoxide mediated synthesis of pyrimidin-4-ones

Org Lett. 2010 May 21;12(10):2270-3. doi: 10.1021/ol100624p.

Abstract

A novel, one-step method for the synthesis of tri- and tetrasubstituted pyrimidin-4-ones is reported. This method involves a titanium(IV)-mediated cyclization involving two sequential condensations of primary and beta-ketoamides. The reaction is operationally facile, readily scalable, and offers rapid entry into differentially substituted pyrimidin-4-one scaffolds. The high functional group compatibility allows for substantial diversification in the products generated from this transformation.

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Pyrimidinones / chemical synthesis*
  • Pyrimidinones / chemistry
  • Stereoisomerism

Substances

  • Organometallic Compounds
  • Pyrimidinones
  • titanium isopropoxide