102
X. Hou et al. / Journal of Organometallic Chemistry 708-709 (2012) 98e105
J ¼ 7.8 Hz, 1H, Py H), 7.27 (d, J ¼ 7.46 Hz, 1H, Py H), 6.94e7.25 (m,
25H, Ph), 6.82 (s, 1H, N]CePh), 6.60 (s, 1H, N]CePh), 5.72 (s, 1H,
eCH(Ph)2), 5.43 (s, 1H, eCH(Ph)2), 2.78, 2.61 (m, 2H, PyeCH2e), 1.27
(m, 2H, N]CeCH2e), 1.93 (s, 3H, PheCH3), 1.14, 0.88 (m, 2H,
C48H40N2 (645): C, 89.40; H, 6.25; N, 4.34%. Found: C, 89.29; H,
6.41; N, 4.16%.
4.2.1.4. 2-Phenyl-8-(2,6-dibenzhydryl-4-isopropylarylimino)-5,6,7-
trihydroquinoline (L4) and N-(2,6-dibenzhydryl-4-(1-methylethyl))-
2-phenyl-5,6-dihydroquinolin-8-amine (L40). This compound was
prepared according to the method described for L1. The product
was a yellow powder and the yield was 37% (0.25 g, 0.37 mmol).
eCH2e) ppm; and for L10:
d
¼ 7.86 (d, J ¼ 7.8 Hz, 1H, Py H), 7.57 (d,
J ¼ 7.9 Hz, 1H, Py H), 6.94e7.25 (m, 25H, Ph), 6.82 (s, 1H, C]NePh),
6.71 (s, 1H, C]NePh), 6.68 (s, 1H, eNHe), 5.68 (s, 1H, eCH(Ph)2),
5.43 (s, 1H, eCH(Ph)2), 4.62 (t, J ¼ 4.3 Hz, 1H, eC]CHe), 2.87 (t,
J ¼ 7.5 Hz, 2H, PyeCH2e), 2.34 (m, 2H, PyeCH2eCH2e), 2.26 (s, 3H,
PheCH3), 1.88 (m, 2H, eCH2e) ppm. 13C NMR (100 MHz, CDCl3 TMS)
for L1: 166.3, 153.5, 149.8, 144.8, 143.1, 142.0, 140.8, 139.3, 138.5,
137.4, 135.5, 133.8, 130.9, 129.7, 128.9, 128.5, 128.3, 126.2, 56.6, 51.8,
27.7, 21.7, 18.8, 18.3 ppm; and for L10: 157.2, 149.3, 144.6, 144.4,
144.2, 139.7, 137.6, 137.2, 130.3, 129.6, 129.5, 128.6, 128.2, 128.0,
127.5, 126.8, 126.1, 118.6, 99.7, 56.4, 52.0, 29.3, 28.6, 23.3 ppm. FT-IR
(KBr, cmꢀ1): 3362, 3023, 2919, 2361, 1974, 1638, 1598, 1575, 1471,
1387, 1026, 739, 694. Anal. Calcd for C48H40N2 (645): C, 89.40; H,
6.25; N, 4.34%. Found: C, 89.27; H, 6.13; N, 4.76%.
M.p.: 134e135 ꢁC 1H NMR (400 MHz, CDCl3 TMS) for L40:
d
¼ 8.09
(d, J ¼ 7.8 Hz, 1H, Py H), 7.37 (d, J ¼ 7.9 Hz, 1H, Py H), 7.04e7.27 (m,
20H, Ph), 6.78 (s, 2H, N]CePh), 5.46 (s, 2H, eCH(Ph)2), 2.73 (m,
1H, eCH(CH3)2), 2.35 (t, J ¼ 7.9 Hz, 2H, PyeCH2e), 1.97 (t,
J ¼ 5.8 Hz, 2H, N]CeCH2e), 1.04 (d, 6H, eCH(CH3)2), 0.73 (m, 2H,
eCH2e) ppm; and for L40:
d
¼ 7.74 (d, J ¼ 7.8 Hz, 1H, Py H), 7.47 (d,
J ¼ 7.9 Hz, 1H, Py H), 7.01e7.27( m, 25H, Ph), 6.83 (s, 2H, C]NePh),
6.43 (s, 1H, eNHe), 5.80 (s, 2H, eCH(Ph)2), 4.45 (t, J ¼ 4.5 Hz, 1H,
eC]CHe), 2.75 (t, J ¼ 7.5 Hz, 2H, PyeCH2e), 2.72 (m, 1H,
eCH(CH3)2), 2.13 (m, 2H, eC]CHeCH2e), 1.09 (d, J ¼ 6.9 Hz, 6H,
eCH(CH3)2) ppm. 13C NMR (100 MHz, CDCl3 TMS) for L4: 164.7,
143.0, 140.0, 139.3, 138.6, 138.0, 129.8, 129.7, 129.4, 129.2, 128.9,
128.6, 128.2, 127.4, 126.7, 126.2, 126.0, 124.1, 52.7, 40.1, 33.3, 29.2,
24.1, 22.9 ppm; and for L40: 156.8, 153.3, 150.4, 148.1, 146.8, 144.9,
143.4, 142.6, 142.2, 138.7, 128.4, 128.3, 127.6, 127.0, 126.9, 126.6,
126.4, 126.2, 99.2, 52.4, 39.2, 33.9, 30.0, 24.1 ppm. FT-IR (KBr,
cmꢀ1): 3349, 3023, 2955, 2344, 1978, 1634, 1600, 1572, 1492, 1386,
1025, 741, 695. Anal. Calcd for C50H44N2 (673): C, 89.25; H, 6.59; N,
4.16%. Found: C, 89.11; H, 6.29; N, 4.07%.
4.2.1.2. 2-Phenyl-8-(2-benzhydryl-4,6-dimethylarylimino)-5,6,7-tri-
hydroquinoline (L2) and N-(2,4-methyl-6-dibenzhydryl)-2-phenyl-
5,6-dihydroquinolin-8-amine (L20). This compound was prepared
according to the method described for L1. The product was a yellow
powder and the yield was 45% (0.22 g, 0.45 mmol). M.p.:
148e149 ꢁC 1H NMR (400 MHz, CDCl3 TMS) for L2:
d
¼ 7.69 (d,
J ¼ 8.1 Hz, 1H, Py H), 7.56 (d, J ¼ 8.0 Hz, 1H, Py H), 7.03e7.22 (m, 15H,
Ph), 6.88 (s, 1H, N]CePh), 6.61 (s, 1H, C]NePh), 5.75 (s, 1H,
eCH(Ph)2), 2.73, 2.58 (m, 2H, PyeCH2e), 2.22 (s, 3H, PheCH3), 2.00
(s, 3H, PheCH3), 1.91, 1.57 (m, 2H, N]CeCH2), 1.13, 0.83 (m, 2H,
4.2.1.5. 2-Chloro-8-(2,4-dibenzhydryl-6-methylarylimino)-5,6,7-tri-
hydroquinoline (L5) and N-(2-methyl-4,6-dibenzhydryl)-2-chloro-
5,6-dihydroquinolin-8-amine (L50). This compound was prepared
according to the method described for L1. The product was a yellow
powder isolated in 41% yield (0.25 g, 0.41 mmol). M.p.: 140e141 ꢁC
eCH2e) ppm; and for L20:
d
¼ 8.08 (d, J ¼ 7.8 Hz, 1H, Py H), 7.54 (d,
J ¼ 7.9 Hz, 1H, Py H),7.03e7.22( m, 15H, Ph), 6.97 (s, 1H, C]NePh),
6.65 (s, 1H, eNeH), 6.61 (s, 1H, C]NePh), 5.67 (s, 1H, eCH(Ph)2),
4.59 (t, J ¼ 4.8 Hz, 1H, C]CHe), 2.85 (t, J ¼ 7.5 Hz, 2H, PyeCH2e),
2.32 (m, 2H, C]CHeCH2e), 2.31 (s, 3H, PheCH3), 2.23 (s, 2H,
PheCH3) ppm. 13C NMR (100 MHz, CDCl3 TMS) for L2: 167.3, 156.4,
149.3, 144.5, 141.9, 139.3, 138.2, 137.7, 135.5, 133.8, 130.9, 129.2,
128.6, 128.1, 127.8, 126.8, 125.9, 122.0, 52.2, 30.5, 29.1, 21.6, 21.5,
18.0 ppm; and for L20: 153.5, 146.6, 143.1, 139.8, 138.7, 137.4, 136.5,
135.0, 131.6, 130.4, 129.6, 128.8, 128.4, 128.0, 127.5, 126.1, 124.9,
118.5, 97.9, 51.8, 27.7, 21.4, 21.2, 18.5 ppm. FT-IR (KBr, cmꢀ1): 3362,
3024, 2917, 2362, 1974, 1640, 1598, 1575, 1470, 1387, 1246, 760, 695.
Anal. Calcd for C36H32N2 (492): C, 87.77; H, 6.55; N, 5.69%. Found: C,
87.88; H, 6.31; N, 5.77%.
1H NMR (400 MHz, CDCl3 TMS) for L5:
d
¼ 7.40 (d, J ¼ 7.8 Hz, 1H, Py
H), 7.27 (d, J ¼ 7.9 Hz, 1H, Py H), 6.94e7.25 (m, 20H, Ph), 6.78 (s, 1H,
N]CePh), 6.55 (s, 1H, N]CePh), 5.57 (s, 1H, eCH(Ph)2), 5.39 (s, 1H,
eCH(Ph)2), 2.66, 2.50 (m, 2H, PyeCH2e), 1.96, 1.44 (m, 2H, N]
CeCH2e), 1.93 (s, 3H, PheCH3), 1.45, 0.95 (m, 2H, eCH2e) ppm;
and for L50:
d
¼ 7.38 (d, J ¼ 7.8 Hz,1H, Py H), 7.24 (d, J ¼ 7.9 Hz,1H, Py
H), 6.94e7.25( m, 20H, Ph), 6.87 (s, 1H, C]NePh), 6.76 (s, 1H, C]
NePh), 6.30 (s, 1H, eNHe), 5.59 (s, 1H, eCH(Ph)2), 5.39 (s, 1H,
eCH(Ph)2), 4.55 (t, J ¼ 4.6 Hz, 1H, eC]CHe), 2.76 (t, J ¼ 7.8 Hz, 2H,
PyeCH2e),2.25 (m, 2H, PyeCH2eCH2e), 2.23 (s, 3H, PheCH3), 1.88
(m, 2H, eCH2e) ppm. 13C NMR (100 MHz, CDCl3 TMS) for L5: 165.8,
150.2,148.1,146.9,144.3,143.4,142.1,140.8,140.0,137.8,137.4,136.9,
135.8, 133.7, 130.8, 130.2, 129.5, 128.3, 126.2, 124.7, 56.6, 52.1, 27.2,
21.5, 18.7, 18.1 ppm; and for L50: 152.8, 150.4, 150.1, 148.3, 144.7,
144.6, 144.1, 143.4, 143.2, 137.6, 132.1, 129.6, 129.2, 128.9, 128.2,
127.9, 126.4, 126.1, 125.9, 122.1, 99.4, 56.4, 51.9, 30.3, 27.2, 21.5 ppm.
FT-IR (KBr, cmꢀ1): 3348, 3028, 2893, 2329, 1978, 1639, 1599, 1573,
1474, 1331, 1124, 755, 696. Anal. Calcd for C42H35ClN2 (602): C,
83.63; H, 5.85; N, 4.64%. Found: C, 83.47; H, 5.77; N, 4.72%.
4.2.1.3. 2-Phenyl-8-(2,6-dibenzhydryl-4-methylarylimino)-5,6,7-tri-
hydroquinoline (L3) and N-(2,6-dibenzhydryl-4-methyl)-2-phenyl-
5,6-dihydroquinolin-8-amine (L30). This compound was prepared
according to the method described for L1. The product was
a yellow powder isolated in 44% yield (0.28 g, 0.44 mmol). M.p.:
187e189 ꢁC 1H NMR (400 MHz, CDCl3 TMS) for L3:
d
¼ 7.56 (d,
J ¼ 8.0 Hz, 1H, Py H), 7.52 (d, J ¼ 8.0 Hz, 1H, Py H), 7.03e7.22 (m,
20H, Ph), 6.79 (s, 2H, C]NePh), 5.61 (s, 2H, eCH(Ph)2), 2.36 (t,
J ¼ 5.88 Hz, 2H, PyeCH2e), 2.22 (s, 3H, PheCH3), 1.12 (t, J ¼ 5.70 Hz,
2H, N]CeCH2e), 0.71 (m, 2H, eCH2e) ppm; and for L30:
d
¼ 8.12
4.2.1.6. 2-Chloro-8-(2-benzhydryl-4,6-dimethylarylimino)-5,6,7-tri-
hydroquinoline (L6) and N-(2,4-methyl-6-dibenzhydryl)-2-chloro-
5,6-dihydroquinolin-8-amine (L60). This compound was prepared
according to the method described for L1. The product was a yellow
powder isolated in 54% yield (0.24 g, 0.54 mmol). M.p.: 178e179 ꢁC
(d, J ¼ 8.1 Hz, 1H, Py H), 7.76 (d, J ¼ 7.9 Hz, 1H, Py H), 7.11e7.39(m,
20H, Ph), 6.83 (s, 2H, C]NePh), 6.47 (s, 1H, eNeH), 5.88 (s, 2H,
eCH(Ph)2), 4.49 (t, J ¼ 4.6 Hz, 1H, C]CHe), 2.78 (t, J ¼ 7.7 Hz, 2H,
PyeCH2e), 2.23 (s, 3H, PheCH3), 2.16 (m, 2H, eCH2e) ppm. 13C
NMR (100 MHz, CDCl3 TMS) for L3: 168.3, 154.5, 150.2, 147.5, 145.2,
143.1, 139.8, 137.5, 136.2, 132.3, 131.2, 130.2, 128.7, 128.3, 127.7,
126.6, 125.8, 120.7, 52.6, 33.4, 29.4, 28.7, 20.9 ppm; and for L30:
153.4, 149.3, 143.5, 139.6, 139.2, 136.6, 135.5, 131.1, 130.7, 130.1,
129.8, 128.8, 128.6, 128.4, 128.0, 126.9, 126.0, 118.5, 99.4, 51.5, 27.6,
21.8, 21.6 ppm. FT-IR (KBr, cmꢀ1): 3354, 3024, 2944, 2361, 1949,
1629, 1598, 1574, 1493, 1386, 1025, 763, 692. Anal. Calcd for
1H NMR (400 MHz, CDCl3 TMS) for L6:
d
¼ 7.43 (d, J ¼ 8.1 Hz, 1H, Py
H), 7.30 (d, J ¼ 8.0 Hz, 1H, Py H), 7.03e7.22 (m, 20H, Ph), 6.87 (s, 1H,
N]CePh), 6.60 (s, 1H, C]NePh), 5.73 (s, 1H, eCH(Ph)2), 2.64, 2.45
(m, 2H, PyeCH2e), 2.23 (s, 3H, PheCH3), 2.21 (s, 3H, PheCH3), 1.89,
1.12 (m, 2H, N]CeCH2), 1.42, 0.90 (m, 2H, eCH2e) ppm; and for
L60:
d
¼ 7.37 (d, J ¼ 7.8 Hz, 1H, Py H), 7.25 (d, J ¼ 7.9 Hz, 1H, Py
H),7.03e7.22( m, 10H, Ph), 6.95 (s, 1H, C]NePh), 6.65 (s, 1H, C]