Regioselective C3 alkenylation of 4 H-pyrido[1,2-a]pyrimidin-4-ones via palladium-catalyzed C-H activation

Chem Asian J. 2014 Sep;9(9):2436-9. doi: 10.1002/asia.201402455. Epub 2014 Jul 2.

Abstract

A general and efficient palladium-catalyzed direct C3 alkenylation of 4H-pyrido[1,2-a]pyrimidin-4-ones using AgOAc/O2 as the oxidant has been developed. A variety of 4H-pyrido[1,2-a]pyrimidin-4-ones were successfully coupled with acrylate esters, styrenes, methylvinylketone, and acrylamide in moderate to excellent yields. The reaction exhibited complete regio- and stereoselectivity. This transformation provides an attractive new approach to functionalize 4H-pyrido[1,2-a]pyrimidin-4-ones.

Keywords: CH activation; alkenylation; homogeneous catalysis; palladium; regioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Pyridines / chemistry*
  • Pyrimidinones / chemistry*
  • Stereoisomerism

Substances

  • Organometallic Compounds
  • Pyridines
  • Pyrimidinones
  • Palladium