Zwitterionic borane adducts of N-heterocyclic carbenes from mesomeric betaines of uracil

Org Biomol Chem. 2014 May 7;12(17):2737-44. doi: 10.1039/c3ob42462f.

Abstract

We prepared a series of imidazolium-substituted uracil-anions which are members of the class of cross-conjugated heterocyclic mesomeric betaines. They are in tautomeric equilibrium with their N-heterocyclic carbenes, uracil-6-yl-imidazol-2-ylidenes. These carbenes can be trapped by reaction with sulfur, selenium, as well as by triethylborane and triphenylborane, respectively. The latter trapping reaction yielded the first representatives of a new heterocyclic zwitterionic ring system, imidazo[2',1':3,4][1,4,2]diazaborolo[1,5-c]pyrimidinium-10-ide. Results of two single crystal X-ray structure analyses are presented.

MeSH terms

  • Anions
  • Betaine / chemistry*
  • Boranes / chemistry*
  • Heterocyclic Compounds / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Models, Molecular
  • Molecular Structure
  • Uracil / chemistry*

Substances

  • Anions
  • Boranes
  • Heterocyclic Compounds
  • carbene
  • Betaine
  • Uracil
  • Methane
  • triethylborane