Synthesis of carbazoles from N-(N,N-diarylamino)phthalimides with aluminum chloride via diarylnitrenium ions.
Generation of diarylnitrenium ions from N-(N,N-diarylamino)phthalimides by treatment with AlCl(3) in benzene or in 1,2-dichloroethane leads to formation of carbazoles by intramolecular C-C bond formation. The reaction proceeds in synthetically useful yields.
Kikugawa
Y
Y
Faculty of Pharmaceutical Sciences, Josai University, 1-1 Keyakidai, Sakado, Saitama 350-0295, Japan. kikugawa@josai.ac.jp
Aoki
Y
Y
Sakamoto
T
T
D000470:Alkaloids / Q000737:chemistry; D000077410:Aluminum Chloride; D017607:Aluminum Compounds; D001554:Benzene / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010797:Phthalimides / Q000737:chemistry*
D000470:Alkaloids; D017607:Aluminum Compounds; D002227:Carbazoles; D002712:Chlorides; D007202:Indicators and Reagents; D010797:Phthalimides; C443728:murrayafoline A; D000077410:Aluminum Chloride; D001554:Benzene