Advances in the stereoselective synthesis of antifungal agents and ...

Chapter 8 186(R,S)-(±)-1-(2-Octyl)imidazole-4,5-dicarbonitrile (±)-33cSynthetic method 7.7.1.Purified by preparative TLC (hexanes/AcOEt 3:1).1H-NMR (200 MHz, CDCl 3 ) δ = 0.88 (t, J = 5.7 Hz, 3H), 1.28 (m,8H), 1.65 (d, J = 5.7 Hz, 3H), 1.93 (m, 2H), 4.43 (sextet, J = 5.7 Hz,1H), 7.75 (s, 1H).IR (CHCl 3 ): ν cm-1= 2240 cm -1 .M.P.= Colorless oil.Elementary Analysis. calcd. for C 13 H 18 N 4 : C, 67.79; H, 7.88; N,24.33. Found: C, 67.92; H, 7.93, N, 24.15.(S)-(+)-1-(2-Octyl)imidazole-4,5-dicarbonitrile(S)-(+)-33cSynthetic method 7.7.1:[α] 0 546 +1.1 (c 2.91, CHCl 3 ).Physical and spectral data were identical with those described abovefor the racemate (±)-33c.(R)-(-)-1-(2-Octyl) imidazole-4,5-dicarbonitrile (R)-(-)-33cSynthetic method 7.7.1[α] 20 546 -1.0 (c 2.18, CHCl 3 ).Physical and spectral data were identical with those described abovefor the racemate (±)-33c.(R,S)-(±)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarbonitrile (±)-33dSynthetic method 7.7.1.Purified by flash chromatography (n-hexane/AcOEt 3:1). Ananalytical sample was prepared by recrystallization frombenzene/cyclohexane.1H-NMR (300 MHz, CDCl 3 ) δ = 1.48 (d, J = 4.3 Hz, 3H), 2.86 (dd, J= 14.1, 4.3 Hz, 2H), 2.93 (dd, J = 14.1, 4.3 Hz, 2H), 4.38 (sextet, J =4.3 Hz, 1H), 6.83 (m, 2H), 7.05 (m, 3H), 7.26 (s, 1H).IR (CHCl 3 ): ν cm-1=2240 cm -1 ;M.P.= 138-140 °C.Elementary Analysis. calcd. for C 14 H 12 N 4 : C, 71.17; H, 5.12; N,23.71. Found: C, 71.33; H, 5.01; N, 23.57.(S)-(+)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarbonitrile(S)-(+)-33d