Med Chem Res (2012) 21:1395–1402
1401
1.05 (d, 6H, J = 6.5 Hz (CH3)2CH), 2.13 (s, 3H, Ar–CH3),
3.22 (m, 1H, J = 6.5 Hz, CH–(CH3)2), 6.13 (s, 1H, Ar–H),
6.57 (s, 1H, Ar–H), 6.86 (s, 1H, Ar–H), 6.93–7.74 (m, 2H,
Ar–H), 7.78 (d, 1H, Ar–H), 8.42 (s, 1H, Ar–OH), 8.97 (s, 1H,
NH–C=O). 13C NMR (ppm): 18.6, 24.7, 24.7, 27.5, 102.8
118.6, 121.3, 113.9, 126.5, 123.1, 128.3, 130.5, 129.5, 136.6,
132.5, 133.9, 151.3, 155.3, 163.5, 169.6; MS m/z: 351, 333,
307.
127.6, 129.9, 133.8, 139.6, 154.3, 155.3, 156.3, 166.8, 164.6,
163.9, MS m/z: 420, 419, 404, 389, 373.
1,2-Dihydro-6-(4-hydroxy-5-isopropyl-5-methylphenyl)-4-
(3,4-dimethoxy phenyl)-2-oxopyridine-3-carbonitrile (IVj)
Yield: 71%, MP: 181–182°C, MF: C24H24N204, IR (cm-1):
3380 (NH), 2219 (CN), 1650 (O=C–NH). 1H NMR
(dppm): 1.31 (d, 6H, (CH3)2CH), J = 6.9 Hz, 2.38 (s, 3H,
Ar–CH3), 3.22 (m, 1H, J = 6.9 Hz, CH–(CH3)2), 3.96 (s,
6H, Ar–OCH3), 6.12 (bs, 1H, Ar–OH), 6.42 (s, 1H, Ar–H),
6.74 (s, 1H, Ar–H), 6.89 (d, 1H, J = 8.0 Hz, Ar–H), 6.96
(d, 1H, J = 8.0 Hz, Ar–H), 7.18 (s, 1H, Ar–H), 7.28 (s, 1H,
Ar–H), 8.13 (s, 1H, NH–C=O). 13C NMR (ppm): 16.5,
23.7, 23.7, 26.5, 56.2, 104.8, 114.3, 115.3, 115.9, 125.1,
119.7, 128.3, 149.0, 111.6, 115.2, 149.7, 125.9, 134.6,
134.9, 152.4, 156.3, 161.6, 166.5; MS m/z: 404, 420, 419,
404, 389, 373.
1,2-Dihydro-6-(4-hydro-5-isopropyl-2-methylphenyl)-2-
oxo-4-(furfural-2-yl) pyridine-3-carbonitrile (IVg)
Yield: 66%, MP: 266–269°C, MF: C22H18N203, IR (cm-1):
3340 (NH), 2220 (CN), 1630 (O=C–NH). 1H NMR
(dppm): 1.30 (d, 6H, J = 6.9 Hz (CH3)2CH), 2.28 (s, 3H,
Ar–CH3), 3.25 (m, 1H, J = 6.9 Hz, CH–(CH3)2), 5.80 (s,
1H, Ar–OH), 6.58 (s, 1H, Ar–H), 6.98 (s, 1H, Ar–H), 7.20
(s, 1H, Ar–H), 7.43 (m, 2H, Ar–H), 7.78 (d, 1H, Ar–H),
8.42 (s, 1H, NH–C=O). 13C NMR (ppm): 15.5, 23.1, 23.1,
26.9, 106.7, 111.4, 113.9, 115.3, 118.8, 119.6, 122.2,
128.3, 132.5, 133.7, 146.9, 147.9, 151.4, 156.3, 163.5,
172.3; MS m/z: 335, 317, 291.
4-(4-Dimethylamino)phenyl-1,2-dihydro-6-(4-hydroxy-5-
isopropyl-2-methyl phenyl)-2-oxopyridine-3-carbonitrile
(IVk)
1,2-Dihydro-4-(4-hydroxy-3-methoxyphenyl)-6-(4-hydro-5-
isopropyl-2-methyl phenyl)-2-oxo-pyridine-3-carbonitrile
(IVh)
Yield: 75%, MP: 160–162°C, MF: C24H25N302, IR (cm-1):
3205 (NH), 2220 (CN), 1599 (O=C–NH) 1H NMR (dppm):
1.22 (d, 6H, J = 6.9 Hz (CH3)2CH), 2.21 (s, 3H, Ar–CH3),
3.10 (m, 6H, N(CH3)2), 3.20 (m, 1H, J = 6.9 Hz, CH–
(CH3)2), 6.12 (bs, 1H, Ar–OH), 6.51 (s, 1H, Ar–H), 6.61 (s,
1H, Ar–H), 7.24 (d, 2H, J = 8.0 Hz, Ar–H), 7.50 (s, 1H,
Ar–H), 7.64 (d, 2H, J = 8.0 Hz, Ar–H), 8.18 (s, 1H, NH–
C=O). 13C (ppm): 20.5, 24.7, 24.7, 27.5, 42.3, 42.3, 106.8,
114.3, 116.2, 117.3, 117.9, 124.1,127.1, 129.3, 130.3,
136.6, 136.9, 151.8, 154.4, 158.3, 163.6, 168.8; MS m/z:
386, 371, 370, 345, 344, 342.
Yield: 71%, MP: 232–235°C, MF: C22H22N204, IR (cm1):
3380 (NH), 2219 (CN), 1650 (O=C–NH), 1H NMR
(dppm): 1.22 (d, 6H, J = 6.8 Hz (CH3)2CH), 2.33 (s, 3H,
Ar–CH3), 3.39 (m, 1H, J = 6.8 Hz, CH–(CH3)2), 3.98 (s,
3H, Ar–OCH3), 6.28 (s, 1H, Ar–H of pyridone), 6.78 (s,
1H, Ar–H), 7.01 (d, 1H, Ar–H), 7.122 (s, 1H, Ar–H), 7.24
(s, 1H, Ar–H), 7.28 (s, 1H, Ar–H), 8.60 (s, 1H, NH–C=O),
13C NMR (ppm): 20.3, 23.4, 23.4, 26.6, 58.4, 104.3, 112.0,
113.8, 115.4, 118.9, 120.0, 123.1, 124.2, 126.4, 126.6,
127.1, 136.6, 137.9, 145.8, 151.3, 154.6, 159.3, 163.8,
168.5; MS m/z: 391, 373, 358, 347.
1,2-Dihydro-6-(4-hydroxy-5-isopropyl-5-methylphenyl)-4-
(2,4,6-trimethoxy phenyl)-2-oxopyridine-3-carbonitrile
(IVl)
1,2-Dihydro-6-(4-hydroxy-5-isopropyl-5-methylphenyl)-4-
(2,4-dimethoxy phenyl)-2-oxopyridine-3-carbonitrile (IVi)
Yield: 78%, MP: 131–132°C, MF: C25H26N205, IR (cm-1):
3200 (NH), 2220 (CN), 1580 (O=C–NH). 1H NMR
(dppm): 1.24 (d, 6H, J = 6.9 Hz, (CH3)2CH), 2.38 (s, 3H,
Ar–CH3), 3.22 (m, 1H, J = 6.9 Hz, CH–(CH3)2), 3.96 (s,
9H, Ar–OCH3), 6.04 (bs, 1H, Ar–OH), 6.40 (s,1H, Ar–H),
6.74 (s, 1H, Ar–H), 6.90 (d, 1H, Ar–H), 7.18 (s, 1H, Ar–H),
8.23 (s, 1H, NH–C=O). 13C NMR (ppm): 15.5, 24.7, 24.7,
25.9, 55.3, 93.6, 94.6, 103.1, 103.8, 114.3, 115.3, 116.0,
126.1, 128.4,129.3, 133.9, 135.6, 154.6, 155.7, 158.3,
160.7, 160.9, 163.3, 166.5; MS m/z: 433, 419, 418, 403,
390, 372.
Yield: 63%, MP: 116–118°C, MF: C23H24N204, IR (cm-1):
3380 (NH), 2219 (CN), 1650 (O=C–NH). 1H NMR (dppm):
1.22 (d, 6H, J = 6.9 Hz (CH3)2CH), 2.28 (s, 3H, Ar–CH3),
3.21 (m, 1H, J = 6.9 Hz, CH–(CH3)2), 3.80 (s, 3H, Ar–
OCH3), 3.90 (s, 3H, Ar–OCH3), 5.70 (bs, 1H, Ar–OH), 6.41
(s, 1H, Ar–H), 6.71 (s, 1H, Ar–H), 6.88 (d, 1H, J = 8.0 Hz,
Ar–H), 7.20 (d, 1H, J = 8.0 Hz, Ar–H), 8.10 (s, 1H, NH–
C=O). 13C NMR (ppm): 20.0, 23.1, 23.1, 26.5, 55.3, 58.1.
104.8,106.8, 109.0, 116.3, 112.3, 118.3, 120.9, 126.1, 126.3,
123