5474
T. Chen et al. / Tetrahedron 67 (2011) 5469e5476
2194, 1627, 1385 cmꢂ1 1H NMR (400 MHz, DMSO-d6) (
. d, ppm):
4.2.16. 7,7-Dimethyl-2-(4-methyl-1H-indol-3-yl)-5-oxo-4-phenyl-
11.65 (s,1H, NH), 9.43 (s,1H, NH), 7.66 (s,1H, ArH), 7.14e7.24 (m, 3H,
ArH), 6.87e7.00 (m, 4H, ArH), 4.96 (s, 1H, CH), 3.79 (s, 3H, CH3),
1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (4{4, 4, 1}). Cream
yellow solid; mp >300 ꢀC. IR (KBr):
n
3256, 3046, 2944, 2188, 1609,
1.99e2.59 (m, 7H, CH2þCH3), 1.06 (s, 3H, CH3), 0.97 (s, 3H, CH3). 13
C
1386 cmꢂ1
.
1H NMR (400 MHz, DMSO-d6) (
d, ppm): 11.59 (s, 1H,
NMR (100 MHz, DMSO-d6) (d, ppm): 194.4, 156.7, 151.1, 143.3, 135.5,
NH), 9.80 (s, 1H, NH), 7.58 (s, 1H, ArH), 7.29e7.34 (m, 5H, ArH),
7.21e7.24 (m, 1H, ArH), 7.07 (s, 1H, ArH), 6.87 (s, 1H, ArH), 4.60 (s,
1H, CH), 2.06e2.53 (m, 7H, CH2þCH3), 1.04 (s, 3H, CH3), 0.95 (s, 3H,
134.2, 128.9, 127.9, 127.0, 124.9, 122.5, 121.4, 121.0, 120.5, 120.1, 117.5,
111.4, 108.2, 107.1, 84.5, 55.6, 50.3, 33.0, 32.0, 29.5, 26.5, 16.8. HRMS:
calculated for C28H27N3O2 [Mþ]: 437.2103, found 437.2101.
CH3). 13C NMR (75 MHz, DMSO-d6) (
d, ppm): 194.5, 150.1, 145.8,
144.5, 136.3, 129.4, 128.5, 127.3, 126.7, 124.8, 122.2, 121.4, 120.6,
110.0, 107.9, 87.6, 50.3, 32.3, 28.8, 27.1, 19.3. HRMS: calculated for
C27H25N3O [Mþ]: 407.1998, found 407.1997.
4.2.22. 2-(1H-Indol-3-yl)-7,7-dimethyl-5-oxo-4-p-tolyl-1,4,5,6,7,8-
hexahydroquinoline-3-carbonitrile (4{6, 1, 1}). Cream yellow solid;
mp >300 ꢀC. IR (KBr):
n
3392, 3250, 3061, 2960, 2190, 1619,
1390 cmꢂ1
.
1H NMR (400 MHz, DMSO-d6) (
d, ppm): 11.75 (s, 1H,
4.2.17. 7,7-Dimethyl-2-(7-methyl-1H-indol-3-yl)-5-oxo-4-phenyl-
1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (4{4, 5, 1}). Cream
NH), 9.57 (s, 1H, NH), 7.70 (s, 1H, ArH), 7.48 (d, 2H, J¼8.0 Hz, ArH),
7.12e7.20 (m, 6H, ArH), 4.54 (s, 1H, CH), 2.02e2.60 (m, 7H,
CH2þCH3), 1.05 (s, 3H, CH3), 0.91 (s, 3H, CH3). 13C NMR (100 MHz,
yellow solid; mp >300 ꢀC. IR (KBr):
n
3259, 3058, 2947, 2190, 1613,
1386 cmꢂ1
.
1H NMR (400 MHz, DMSO-d6) (
d, ppm): 11.77 (s, 1H,
NH), 9.60 (s, 1H, NH), 7.76 (d, 1H, J¼7.6, ArH), 7.30e7.36 (m, 5H,
ArH), 7.22 (t, 1H, J¼6.0 Hz, ArH), 6.98e7.04 (m, 2H, ArH), 4.59 (s, 1H,
CH), 3.86 (s, 3H, CH3), 2.03e2.61 (m, 7H, CH2þCH3), 1.06 (s, 3H,
DMSO-d6) (d, ppm): 194.6, 150.1, 143.4, 143.1, 136.0, 135.7, 129.0,
127.6, 127.2, 125.0, 122.1, 121.1, 120.0, 119.9, 112.2, 108.2, 107.5, 84.8,
50.3, 38.3, 32.0, 29.3, 26.5, 20.7. LCeMS: calculated for C27H26N3O
[MHþ]: 408.2070, found 408.2076.
CH3), 0.92 (s, 3H, CH3). 13C NMR (75 MHz, DMSO-d6) (
d, ppm):
194.6, 150.3, 146.2, 143.4, 135.6, 128.5, 127.2, 126.7, 124.8, 122.6,
121.5, 121.1, 120.2, 117.5, 108.1, 107.9, 84.6, 50.3, 32.0, 29.3, 26.6, 16.8.
HRMS: calculated for C27H25N3O [Mþ]: 407.1998, found 407.1999.
4.2.23. 7,7-Dimethyl-2-(1-methyl-1H-indol-3-yl)-5-oxo-4-p-tolyl-
1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (4{6, 2, 1}). Cream
yellow solid; mp 289e290 ꢀC. IR (KBr):
n
3277, 3057, 2955, 2199,
1629, 1373 cmꢂ1
.
1H NMR (400 MHz, DMSO-d6) (
d
, ppm): 9.54 (s,
4.2.18. 2-(1H-Indol-3-yl)-4-(2-methoxyphenyl)-7,7-dimethyl-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (4{5, 1, 1}). Cream
1H, NH), 7.80 (s, 1H, ArH), 7.54 (d, 1H, J¼8.0 Hz, ArH), 7.49 (d, 1H,
J¼7.6 Hz, ArH), 7.26 (t, 1H, J¼7.6 Hz, ArH), 7.12e7.20 (m, 5H, ArH),
4.54 (s, 1H, CH), 3.85 (s, 3H, CH3), 2.02e2.59 (m, 7H, CH2þCH3), 1.05
yellow solid; mp 270e271 ꢀC. IR (KBr):
n
3336, 3060, 2958, 2199,1610,
1383 cmꢂ1. 1H NMR (400 MHz, DMSO-d6) (
d, ppm): 11.65 (s, 1H, NH),
(s, 3H, CH3), 0.91 (s, 3H, CH3). 13C NMR (100 MHz, DMSO-d6) (
d,
9.43 (s, 1H, NH), 7.67 (s, 1H, ArH), 7.41e7.47 (m, 2H, ArH), 7.09e7.18
(m, 4H, ArH), 7.00 (d, 1H, J¼7.2 Hz, ArH), 6.89 (s, 1H, ArH), 4.96 (s,1H,
CH), 3.80 (s, 3H, CH3),1.99e2.59 (m, 4H, CH2),1.06 (s, 3H, CH3), 0.97 (s,
ppm): 194.6, 150.0, 143.4, 142.6, 136.5, 135.7, 131.4, 129.1, 127.1,
125.3, 122.2, 121.0, 120.3, 120.1, 110.6, 108.2, 106.5, 84.8, 50.2, 39.6,
38.3, 32.0, 29.3, 26.5, 20.7. HRMS: calculated for C28H27N3O [Mþ]:
421.2154, found 421.2150.
3H, CH3). 13C NMR (100 MHz, DMSO-d6) (
d, ppm): 194.2, 156.6, 151.0,
143.1, 135.9, 134.1, 128.9, 127.8, 127.2, 125.0, 122.0, 120.8, 120.4, 119.8,
112.0, 111.4, 107.7, 107.1, 84.5, 55.6, 50.3, 33.0, 31.9, 29.3, 26.4. HRMS:
calculated for C27H25N3O2 [Mþ]: 423.1947, found 423.1943.
4.2.24. 7,7-Dimethyl-2-(7-methyl-1H-indol-3-yl)-5-oxo-4-p-tolyl-
1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (4{6, 5, 1}). Cream
yellow solid; mp >300 ꢀC. IR (KBr):
n
3273, 3059, 2948, 2198, 1630,
4.2.19. 4-(2-Methoxyphenyl)-7,7-dimethyl-2-(1-methyl-1H-indol-3-
1385 cmꢂ1. 1H NMR (400 MHz, DMSO-d6) (
d, ppm): 11.72 (s,1H, NH),
yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
1}). Cream yellow solid; mp >300 ꢀC. IR (KBr):
3291, 3066, 2954,
2195,1630,1374 cmꢂ1.1H NMR (400 MHz, DMSO-d6) (
, ppm):9.49 (s,
(4{5,
2,
n
9.51 (s, 1H, NH), 7.73 (s, 1H, ArH), 7.30 (d, 1H, J¼7.2 Hz, ArH), 7.19 (d,
2H, J¼7.2 Hz, ArH), 7.13 (d, 2H, J¼7.2 Hz, ArH), 7.00e7.04 (m, 2H,
ArH), 4.54 (s,1H, CH), 2.02e2.59 (m,10H, CH2þCH3),1.05 (s, 3H, CH3),
d
1H, NH), 7.74 (s, 1H, ArH), 7.52 (d, 1H, J¼8.0 Hz, ArH), 7.42 (d, 1H,
J¼8.0 Hz, ArH), 7.13e7.24 (m, 4H, ArH), 7.00 (d, 1H, J¼8.0 Hz, ArH),
6.89 (s, 1H, J¼7.2 Hz, ArH), 4.95 (s, 1H, CH), 3.83 (s, 3H, CH3), 3.79 (s,
0.91 (s, 3H, CH3).13C NMR (100 MHz, DMSO-d6) (
d, ppm): 194.6,150.1,
143.4, 143.2, 135.7, 135.6, 129.1, 127.2, 124.8, 122.6, 121.5, 121.1, 120.2,
117.5, 108.2, 107.9, 84.8, 50.3, 38.3, 32.0, 29.3, 26.5, 20.7, 16.8. HRMS:
calculated for C28H27N3O [Mþ]: 421.2154, found 421.2157.
3H, CH3),1.99e2.59(m, 4H, CH2),1.06 (s, 3H, CH3), 0.96(s, 3H, CH3).13
C
NMR (100 MHz, DMSO-d6) (d, ppm): 194.3, 156.6, 151.0, 142.7, 136.4,
134.1, 131.2, 128.8, 127.9, 125.4, 122.1, 120.9, 120.4, 120.1, 120.0, 111.4,
110.5, 107.1, 106.7, 84.4, 55.6, 50.3, 39.6, 33.0, 32.8, 32.0, 29.4, 26.4.
LCeMS: calculated for C28H28N3O2 [MHþ]: 438.2176, found 438.2176.
4.2.25. 2-(1H-Indol-3-yl)-4-(4-methoxyphenyl)-7,7-dimethyl-5-oxo-
1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (compound 4{7, 1,
1}). Cream yellow solid; mp 298e300 ꢀC. IR (KBr):
n
3273, 3065,
1H NMR (400 MHz, DMSO-d6)
d, ppm): 11.74 (s, 1H, NH), 9.54 (s, 1H, NH), 7.77 (s, 1H, ArH), 7.49
2958, 2189, 1617, 1385 cmꢂ1
.
4.2.20. 4-(2-Methoxyphenyl)-7,7-dimethyl-2-(4-methyl-1H-indol-3-
yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
1}). Cream yellow solid; mp >300 ꢀC. IR (KBr):
3323, 3054, 2952,
2184, 1604, 1386 cmꢂ1 1H NMR (400 MHz, DMSO-d6) (
, ppm):
(4{5,
4,
(
n
(d, 2H, J¼7.6 Hz, ArH), 7.19e7.24 (m, 3H, ArH), 7.13 (t, 1H, J¼7.2 Hz,
ArH), 6.91 (d, 2H, J¼8.0 Hz, ArH), 4.54 (s, 1H, CH), 3.75 (s, 3H, CH3),
2.04e2.60 (m, 4H, CH2), 1.07 (s, 3H, CH3), 0.93 (s, 3H, CH3). 13C NMR
.
d
11.47 (s, 1H, NH), 9.60 (s, 1H, NH), 7.44 (s, 1H, ArH), 7.27 (d, 1H,
J¼8.0 Hz, ArH), 7.18 (t, 1H, J¼7.6 Hz, ArH), 7.13 (d, 1H, J¼7.2 Hz, ArH),
7.05 (t, 1H, J¼7.2 Hz, ArH), 6.98 (d, 1H, J¼8.0 Hz, ArH), 6.90 (t, 1H,
J¼7.6 Hz, ArH), 6.83 (s, 1H, ArH), 5.02 (s, 1H, CH), 3.79 (s, 3H, CH3),
(100 MHz, DMSO-d6) (d, ppm): 194.5, 158.0, 149.8, 142.9, 138.5,
136.0, 128.2, 127.4, 125.0, 122.0, 121.0, 120.0, 119.8, 113.7, 112.1, 108.3,
107.5, 84.9, 54.9, 50.2, 39.6, 37.8, 31.9, 29.2, 26.5. HRMS: calculated
for C27H25N3O2 [Mþ]: 423.1947, found 423.1951.
2.02e2.49 (m, 7H, CH2þCH3), 1.04 (s, 3H, CH3), 1.00 (s, 3H, CH3). 13
C
NMR (75 MHz, DMSO-d6) (d, ppm): 194.3, 156.4, 150.9, 144.5, 136.2,
134.0, 129.5, 128.8, 127.8, 126.8, 124.8, 122.1, 121.3, 120.5, 111.3,
109.9, 108.2, 106.8, 87.7, 55.6, 50.4, 32.2, 28.9, 27.0, 19.2. HRMS:
calculated for C28H27N3O2 [Mþ]: 437.2103, found 437.2102.
4.2.26. 4-(4-Methoxyphenyl)-7,7-dimethyl-2-(1-methyl-1H-indol-3-
yl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile
1}). Cream yellow solid; mp 254e255 ꢀC. IR (KBr):
2953, 2197, 1607, 1376 cmꢂ1 1H NMR (400 MHz, DMSO-d6) (
d,
(4{7,
2,
n
3260, 3073,
.
4.2.21. 4-(2-Methoxyphenyl)-7,7-dimethyl-2-(7-methyl-1H-indol-3-yl)-
ppm): 9.53 (s, 1H, NH), 7.80 (s, 1H, ArH), 7.54 (d, 1H, J¼8.0 Hz, ArH),
7.49 (d, 1H, J¼8.0 Hz, ArH), 7.15e7.28 (m, 4H, ArH), 6.89 (d, 2H,
J¼7.6 Hz, ArH), 4.53 (s, 1H, CH), 3.86 (s, 3H, CH3), 3.73 (s, 3H, CH3),
5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (4{5, 5, 1}). Cream
yellow solid; mp 206e208 ꢀC. IR (KBr):
n 3415, 3272, 3060, 2956,