2D 1H and 13C NMR evidence for stereoselective formation of a new bond C-N, C-S or C-C in the reaction of ivalin acetate with substituted pyrimidines

Spectrochim Acta A Mol Biomol Spectrosc. 1998 Apr;54A(4):567-74. doi: 10.1016/s1386-1425(97)00245-x.

Abstract

Several pyrimidine derivatives of ivalin acetate were synthesized as potential anti HIV agents. High stereoselective Michael addition to ivaline acetate was observed and a new C-C, C-N or C-S bond was formed. 2D NMR 1H and 13C as well as X-ray crystallographic studies were performed on the compounds herein described to establish the structure and stereochemistry.

MeSH terms

  • Alkylation
  • Anti-HIV Agents / chemistry*
  • Carbon
  • Crystallography, X-Ray
  • Lactones*
  • Models, Chemical
  • Models, Molecular
  • Nitrogen
  • Protein Conformation
  • Pyrimidines / chemistry*
  • Sesquiterpenes / chemistry*
  • Stereoisomerism
  • Sulfur

Substances

  • Anti-HIV Agents
  • Lactones
  • Pyrimidines
  • Sesquiterpenes
  • ivalin
  • Sulfur
  • Carbon
  • Nitrogen