Ring transformation of unsaturated N-bridgehead fused pyrimidin-4(3H)-ones: role of repulsive electrostatic nonbonded interaction

J Org Chem. 2011 Jan 21;76(2):696-9. doi: 10.1021/jo102079k. Epub 2010 Dec 15.

Abstract

Thermal ring transformation ability of unsaturated N-bridgehead fused pyrimidin-4(3H)-ones A is governed by both the steric and the electrostatic interactions between the oxygen of the carbonyl group and the substituent in the peri position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Cycloparaffins / chemistry*
  • Heterocyclic Compounds, 2-Ring / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrimidinones / chemistry*

Substances

  • Cycloparaffins
  • Heterocyclic Compounds, 2-Ring
  • Pyrimidinones