2900
Med Chem Res (2012) 21:2896–2901
5-[1-(2-Biphenyl-4-yl-2-oxo-ethyl)-2-phenyl-1H-indol-3-
ylmethylene]-pyrimidine-2,4,6-trione (5d)
6.024 (m, 1H) 7.25–7.65 (m, 9H), 7.96 (s, 1H), 10.98 (s,1H,
NH), 11.05 (s, 1H, NH). 13C-NMR (100 MHz, DMSO-d6): d
46.9, 48.5, 111.5, 111.6, 112.9, 117.2, 121.6, 123.3, 124.7,
125.2, 128.7, 130.2, 130.9, 133.0, 137.4, 147.3, 150.4, 151.4,
161.4, 164. MS ESI 371 (m ?) (40%), 372(m ? 1) (20%).
For the M.F C22H17N3O3 M.Wt 371.
Orange solid; M.P 250–255°C; IR (KBr, tmax, cm-1):
3225, 3192 (N–H), 3070(aromatic C–H), 2929(aliphatic
C–H), 1709, 1672,1665(C=O), 1538, 1447, 1284, 1187, 944,
1
753; H-NMR (400 MHz, DMSO-d6): d 6(s, 2H), 7.3–7.76
(m, 16H), 7.89(d, 1H, J = 8.4 Hz) 7.99 (s, 1H), 8.147
(d, 1H, J = 8.4 Hz), 11.03(s, 1H, NH), 11.09(s, 1H, NH).
13C-NMR (100 MHz, DMSO-d6): d 51.6, 111.2, 111.9,
113.1, 121.5,123.3, 124.6, 125.1, 127.0, 128.5, 128.7, 128.9,
129.1, 130.2, 130.4, 130.7, 132.7, 138.3, 138.6, 145.6, 147.2,
150.4, 151.9, 161.4, 164.0, 192.9. MS ESI: 526 (m ? 1)
(10%). For the M.F C33H23N3O4, M.Wt 525.
5-(1-Butyl-2-phenyl-1H-indol-3-ylmethylene)-pyrimidine-
2,4,6-trione (6c)
Orange solid; M.P 220–230°C; IR (KBr, tmax, cm-1): 3203,
3080 (N–H), 2931 (aliphatic C–H), 1727, 1688 (C=O),
1
1550, 1443, 1295, 970, 749; H-NMR (400 MHz, DMSO-
d6): d 0.691 (t, J = 7.2 Hz, 3H, CH3–CH2), 1.07 (m, 2H),
1.58 (m, 2H), 4.272 (t, J = 7.2 Hz, 2H, CH2–CH2), 7.2–7.7
(m, 9H), 7.9 (s, 1H), 10.96 (s, 1H, NH), 11.03 (s, 1H, NH).
13C-NMR (100 MHz, DMSO-d6): d 13.1, 19.1, 31.0, 43.9,
110.9, 111.3, 112.9, 121.5, 123.3, 124.9, 125.2, 128.7,
130.1, 131.0, 137.3, 147.3, 150.4, 151.9, 161.4, 164.1. MS
HRMS Calculated 387.16 found 387.084, 388.09 (m ? 1),
410.077 (m ? 23) For the M.FC23H21N3O3.
5-{1-[2-(4-Methoxy-phenyl)-2-oxo-ethyl]-2-phenyl-1H-
indol-3-ylmethylene]-pyrimidine-2,4,6-trione (5e)
Yellowish solid, M.P 265–270°C, IR (KBr, tmax, cm-1):
3179, 3104, (N–H) 3030(aromatic C–H), 2932(aliphatic
C–H), 1729, 1693, 1650(C=O),1513, 1440, 1220, 1081,
1
938, 760. H-NMR (400 MHz, DMSO-d6): d 3.8 (s, 3H)
Acknowledgments The authors wish to thank Dr. B. Srinivas, NIT
Warangal for interpreting the single crystal X-ray analysis, one of the
authors S.V thanks the Ministry of Human Resource Development for
providing the fellowship.
5.8 (s, 2H), 7.0–8.0 (m, 10H), 7.565 (d, 1H, J = 6 Hz),
7.101 (d, 1H, J = 8.8 Hz), 7.97 (s, 1H), 8.041 (d,1H,
8.8 Hz), 11.02 (s, 1H, NH), 11.08 (s, 1H, NH). 13C-NMR
(100 MHz, DMSO-d6): d 51.2, 55.6, 111.2, 111.8, 113.1,
114.1, 121.5, 123.3, 124.6, 125.0, 126.8, 128.5, 128.7,
130.2, 130.6, 130.7, 138.3, 147.2, 150.4, 152.0, 161.4,
163.9, 164.0, 191.5. MS ESI: 502 (m ? 23) (60%). For the
M.F C28H21N3O5, M.Wt 479.
Declaration of interest The author reports no conflicts of interest.
The author alone hereby stands responsible for the contents of this
scientific paper.
5-(1-Ethyl-2-phenyl-1H-indol-3-ylmethylene)-pyrimidine-
2,4,6-trione (6a)
References
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Orange Solid; M.P 245–250°C; IR (KBr, tmax, cm-1):
3170, 3090(N–H), 3040(aromatic C–H), 1721,1685 (C=O),
1
1536, 1484, 1231, 936, 758; H-NMR (400 MHz, DMSO-
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J = 6.8 Hz, 2H, CH2-CH3), 7.26–7.7 (m, 9H), 7.93 (s, 1H),
10.95(s, 1H, NH),11.02(s, 1H, NH). 13C-NMR (100 MHz,
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124.8, 125.2, 128.7, 130.1, 131.0, 137.3, 147.3, 150.4,
151.9, 162.4, 163.1. MS ESI 360 (m ? 1) (50%). For the
M.F C21H17N3O3 M.Wt 359.
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Yellowish solid; M.P 220–225°C; IR (KBr, tmax, cm-1):
3186(N–H), 3050, 2831, 1729, 1686 (C=O), 1530, 1440,
1225, 943, 746; 1H-NMR (400 MHz, DMSO-d6): d 4.866 (d,
J = 3.6 Hz, 2H, CH2–CH),4.950–4.907 (d, J = 17.2,1H,
H–C=C–H trans) 5.195(d, 1H, J = 10.4, H–C=C–H cis),
123