Synthesis of heterocyclic compounds via nucleophilic aroylation catalyzed by imidazolidenyl carbene.
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.
Suzuki
Yumiko
Y
School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan. suzuyumi@u-shizuoka-ken.ac.jp
Toyota
Tomonori
T
Miyashita
Akira
A
Sato
Masayuki
M
D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure
C516814:1,3-dimethylimidazolium; D006571:Heterocyclic Compounds; D007093:Imidazoles