Synthesis of heterocyclic compounds via nucleophilic aroylation catalyzed by imidazolidenyl carbene

Chem Pharm Bull (Tokyo). 2006 Dec;54(12):1653-8. doi: 10.1248/cpb.54.1653.

Abstract

Xanthones and acridones were synthesized from 3,4-difluoronitrobenzene and 2-fluorobenzaldehydes in two or three steps. The key step was nucleophilic aroylation catalyzed by imidazolidenyl carbene. The nucleophilic aroylation of 3,4-difluoronitrobenzene afforded 2,2'-difluoro-4-nitrobenzophenones. The cyclization of the difluorobenzophenones with O-nucleophile and N-nucleophile yielded 3-nitroxanthones and 3-nitroacridones, respectively. Indazole, quinolino[2,3-b]quinoxaline, and thianaphtho[2,3-b]quinoxaline derivatives were also synthesized via nucleophilic aroylation of 2,3-dichloroquinoxaline followed by cyclization with nucleophiles.

MeSH terms

  • Catalysis
  • Heterocyclic Compounds / chemical synthesis*
  • Imidazoles / chemistry*
  • Molecular Structure

Substances

  • 1,3-dimethylimidazolium
  • Heterocyclic Compounds
  • Imidazoles