ELECTROORGANIC REACTIONS .35. EFFICIENT CARBON-OXYGEN BOND FORMATION IN THE ANODIC COUPLING OF PYRIDOPYRIMIDINE DERIVATIVES

GÜLLÜ M., RAZACK L., UTLEY J., KING R., WHITE G.

TETRAHEDRON, vol.47, no.4-5, pp.675-684, 1991 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 47 Issue: 4-5
  • Publication Date: 1991
  • Doi Number: 10.1016/s0040-4020(01)87057-5
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.675-684
  • Ankara University Affiliated: Yes

Abstract

4-H-Pyrido[1,2-a]pyrimidine-2,4-diones (Chichibabin) derivatives, formed by condensation of 2-aminopyridines with substituted dialkylmalonates, are electroactive. In solution in CH2Cl2/CF3CO2H mixtures they are smoothly and selectively anodically coupled in high yield. The products are novel and unexpected; radical coupling at the C-3 and O-4 positions is involved and the proposed mechanism is analogous to that of oxidative phenolic coupling.