Carbon disulfide promoted reactions of 2-chloro-4,5-dihydro-imidazole with some N-nucleophiles.
The reactions of 2-chloro-4,5-dihydroimidazole 1 with o-substituted anilines and azoles promoted by carbon disulfide have been carried out. Ab initio MO calculations were used to elucidate the mechanism of the reaction of 1 with N-nucleophilic reagents. A facile synthesis of 2-(4,5-dihydroimidazol-2-yl)-1H-indazole 3e bearing structural resemblances to 2-BFI, a potent and selective agonist of imidazoline I2 receptors, is also described. Structure of 3e was confirmed by NMR spectroscopy and X-ray analysis.
Saczewski
F
F
Department of Chemical Technology of Drugs, Medical University of Gdańsk, Poland. saczew@farmacja.amg.gda.pl
Saczewski
J
J
Gdaniec
M
M
D000814:Aniline Compounds / Q000737:chemistry; D001393:Azoles / Q000737:chemistry; D002246:Carbon Disulfide / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D017550:Spectroscopy, Fourier Transform Infrared
C446976:2-chloro-4,5-dihydroimidazole; D000814:Aniline Compounds; D001393:Azoles; D007093:Imidazoles; D002246:Carbon Disulfide