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HETEROCYCLES, Vol. 65, No. 2, 2005
IR (KBr): 3220 (-NH), 1620 (C=N) cm-1; MS m/z: 424 (M+). Anal. Calcd for C30H36N2. C, 84.90; H, 8.49;
N, 6.60. Found: C, 84.77; H, 8.41; N, 6.80.
cis-2,4,5-Tris(m-nitrophenyl)imidazoline (2g):
1
This imidazoline was prepared in the general way and had mp 130-142° C (ethanol). H-NMR, δH
(CD3SOCD3, TMS): 5.82 (s, 2H), 7.32-7.45 (m, 4H), 7.81-7.89 (m, 5H), 8.44-8.53 (m, 3H), 8.89 (s, 1H);
13C-NMR, δc (CDCl3, TMS): 61.04, 121.99, 122.29, 122.56, 126.07, 129.61, 130.75, 131.46, 134.20,
142.25, 147.50, 148.34, 162.97; IR (KBr): 3379 (-NH), 1610 (C=N) cm-1; MS m/z: 433 (M+). Anal. Calcd
for C21H15N5O6. C, 58.20; H, 3.46; N, 16.16. Found: C, 58.45; H, 3.66; N, 16.32.
cis-2,4,5-Tris(o-chlorophenyl)imidazoline (2h) :
1
This imidazoline was prepared in the general way and had mp 132-134° C (ethanol). H-NMR, δH
(CD3SOCD3, TMS): 6.04 (s, 2H), 6.94-7.01 (m, 4H), 7.09-7.26 (m, 4H), 7.36-7.48 (m, 3H), 7.97 (d, 1H,
J=7.5 Hz) ; 13C-NMR, δc (CDCl3, TMS): 61.79, 123.26, 127.22, 128.26, 129.61, 130.41, 130.66, 130.98,
131.93, 132.03, 132.20, 132.81, 135.15, 164.88; IR (KBr): 3200 (-NH), 1610 (C=N) cm-1; MS m/z: 400
(M+). Anal. Calcd for C21H15 N2Cl3. C, 62.76; H, 3.74; N, 6.97. Found: C, 62.96; H, 3.98; N, 6.97.
cis-2,4,5-Tris(α-naphthyl)imidazoline (2i):
1
This imidazoline was prepared in the general way and had mp 240-242° C (ethanol). H-NMR
(CD3SOCD3/TMS-500 MHz): 6.39 (2H, s), 6.98-7.01 (3H, m), 7.09-7.27 (6H, m), 7.36 (2H, d, J=8.1 Hz),
7.46-7.59 (6H, m), 7.76 (2H, d, J=8.2 Hz), 7.92-7.97 (3H, m), 8.81 (1H, m); 13C-NMR
(CD3SOCD3/TMS-125.7 MHz): 66.6, 125.3, 125.6, 126.0 127.1, 127.6, 127.7, 127.8, 128.1, 128.3, 129.0,
132.7, 132.8, 134.4, 138.4, 164.25; IR (KBr): 3140 (-NH), 1590 (C=N) cm-1; MS m/z: 448 (M+). Anal.
Calcd for C33H24N2. C, 88.39; H, 5.36; N, 6.25. Found: C, 88.22; H, 5.45; N, 6.08.
cis-2,4,5-Tris(β-naphthyl)imidazoline (2j):
1
This imidazoline was prepared in the general way and had mp 208-209°C (ethanol). H-NMR
(CD3SOCD3/TMS-500 MHz): 6.39 (2H, s), 6.92-7.03 (3H, m), 7.06-7.13 (2H, m), 7.14-7.23 (4H, m), 7.33
(2H, d, J=6.9 Hz), 7.46-7.51 (3H, m), 7.55-7.59 (2H, m), 7.76 (2H, d, J=8.5 Hz), 7.92-7.97 (3H, m), 8.82
(1H, m); 13C-NMR (CD3SOCD3/TMS-125.7 MHz): 65.16, 122.98, 124.31, 124.79, 124.86, 124.92, 125.19,
125.50, 126.40, 127.30, 127.36, 127.42, 128.09, 128.56, 130.57, 131.51, 132.85, 133.45, 165.73; IR (KBr):
3412 (-NH), 1620 (C=N) cm-1; MS m/z: 448 (M+). Anal. Calcd for C33H24N2. C, 88.39; H, 5.36; N, 6.25.
Found: C, 88.18; H, 5.48; N, 5.98.
REFERENCES
1.
a) E. J. Corey and M. J. Grogan, Org. Lett., 1999, 1, 157; b) T. Isobe, K. Fukuda, Y. Araki, and T.
Ishikawa, Chem. Commun., 2001, 243; c) M. Anastassiadou, G. Baziard-Mouysset, and M. Payard,
Synthesis, 2000, 1814; d) E. J. Corey and H. C. Huang, Tetrahedron Lett., 1989, 30, 5235; e) E. J.