Mar-Apr 2004
Substituted and Unsubstituted 5-Benzoylbarbituric Acids
243
13
(2H, d, J=4.5 Hz), and 3.03 ppm (3H, s); C-NMR (DMSO-d ,
MHz): δ 158, 148, 147, 140, 133, 133, 126, 125, 125, 124, 123,
119, 113, and 78 ppm.
6
500 MHz): δ 158, 157, 155, 153, 149, 140, 132, 126, 126, 125,
124, 120, 113, 111, 77, and 22 ppm.
Preparation of 4-{N'-[(1,3-Dimethyl-2,4,6-trioxotetrahydropy-
rimidin-5-ylidene)phenylmethyl]hydrazino}-benzoic Acid (2f).
Preparation of 1-Butyl-5-[[N'-(2,4-dinitrophenyl)hydrazino]-(4-
hydroxyphenyl)-methylene]pyrimidine-2,4,6-trione (2l).
This compound was prepared in 79% isolated yield by follow-
1
ing General Procedure E. H-NMR (CF CO H-DMSO-d , 500
This compound was prepared in 80% isolated yield by follow-
1
ing General Procedure E. H-NMR (DMSO-d , 500 MHz): δ
3
2
MHz): δ 7.55 (2H, d, J=8.5 Hz), 7.01 (1H, t, J=7.5 Hz), 6.95 (2H,
6
6
t, J=7.5 Hz), 6.81 (2H, d, J=7.5 Hz), 6.36 (2H, d, J=8.5 Hz), and
13
2.95 ppm (6H, s); C-NMR (CF CO H-DMSO-d , 500 MHz):
11.34 (1H, s), 10.98 (1H, s), 8.86 (1H, d, J=2.5 Hz), 8.36 (1H, d,
J=12.0 Hz), 8.05 (1H, d, J=9.5 Hz), 7.63 (2H, d, J=8.5 Hz), 6.79
(2H, d, J=8.5 Hz), 3.72 (2H, t, J=7.5 Hz), 1.50 (2H, m), 1.26 (2H,
3
2
6
δ 175, 173, 165, 153, 151, 132, 131, 130, 129, 126, 120, 112, 90,
13
and 28 ppm.
m), and 0.86 ppm (3H, t, J=7.5 Hz); C-NMR (DMSO-d , 500
6
MHz): δ 157, 156, 155, 149, 147, 140, 133, 126, 125, 125, 124,
119, 113, 111, 78, 26, 26, 16, and 10 ppm.
Preparation of 5-{(4-Methoxyphenyl)-[N'-(4-nitrophenyl)-
hydrazino]methylene}-1,3-dimethylpyrimidine-2,4,6-trione (2g).
Preparation of 5-[[N'-(2,4-Dinitrophenyl)-hydrazino]-(4-hydroxy-
phenyl)methylene]-pyrimidine-2,4,6-trione (2m).
This compound was prepared in 82% isolated yield by follow-
1
ing General Procedure E. H-NMR (CF CO H-DMSO-d , 500
3
MHz): δ 9.51 (1H, s), 8.03 (2H, d, J=9.0 Hz), 7.16 (2H, d, J=9.0
2
6
This compound was prepared in 91% isolated yield by following
1
General Procedure E. H-NMR (DMSO-d , 500 MHz): δ 11.36
Hz), 6.86 (2H, d, J=9.0 Hz), 6.75 (2H, d, J=9.0 Hz), 3.73 (3H, s),
13
6
(1H, s), 10.79 (2H, s), 8.85 (1H, d, J=2.1 Hz), 8.36 (1H, d, J=10.5
Hz), 8.04 (1H, d, J=9.9 Hz), 7.63 (2H, d, J=8.7 Hz), and 6.78 ppm
and 3.11 ppm (3H, s); C-NMR (CF CO H-DMSO-d , 500
MHz): δ 162.8, 158.0, 150.5, 151.6, 149.8, 137.3, 132.6, 128.3,
3 2 6
13
(2H, d, J=9.0 Hz); C-NMR (DMSO-d , 500 MHz): δ 158, 156,
126.1, 113.1, 110.4, 81.2, 53.4, and 26.5 ppm.
A n a l. Calcd for C
6
147, 147, 140, 133, 126, 126, 125, 123, 118, 113, 111, and 78 ppm.
H
N O : C, 56.47; H, 4.50; N, 16.46.
2o 19 5 6
Found C, 56.33; H, 4.58; N, 16.38.
A n a l. Calcd for C
H N O : C, 47.67; H, 2.82; N, 19.62.
17 12 6 8
Found C, 47.55; H, 2.93; N, 19.54.
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(4-methoxy-
phenyl)methylene]-1,3-dimethyl-pyrimidine-2,4,6-trione (2h) .
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(4-hydroxy-
phenyl)methylene]-1-phenylpyrimidine-2,4,6-trione (2n).
This compound was prepared in 81% isolated yield by following
1
General Procedure E. H-NMR (CF CO H-DMSO-d , 500
This compound was prepared in 83% isolated yield by follow-
1
ing General Procedure E. H-NMR (DMSO-d , 500 MHz): δ
3
MHz): δ 9.51(1H, s), 8.62(1H, d, J=2.5 Hz), 8.01 (1H, d, J=9 Hz),
2
6
6
6.94 (1H, d, J=9 Hz), 6.83 (2H, d, J=7 Hz), 6.56 (2H, d, J=7Hz),
13
3.44 (3H, s), and 2.97 ppm (6H, s): C-NMR (CF CO H-DMSO-
11.52 (1H, s), 10.37 (1H, s), 8.87 (1H, d, J=2.7 Hz), 8.33 (1H, d,
J=12.0 Hz), 8.03 (1H, d, J=9.9 Hz), 7.67 (2H, d, J=9.0 Hz), 7.38
(2H, t, J=7.4 Hz), 7.28 (1H, t, J=7.5 Hz), 7.19 (2H, d, J=8.4 Hz),
and 6.76 ppm (2H, d, J=8.4 Hz); C-NMR (DMSO-d , 500
6
MHz): δ 158, 157, 156, 149, 147, 140, 133, 132, 126, 126, 125,
3
d , 500 MHz): δ 176.2, 165.5, 163.2, 153.1, 146.5, 139.5, 131.2,
2
6
128.6, 123.8, 123.4, 114.9, 109.3, 92.1, 55.4, and 28.4 ppm.
13
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(4-methoxy-
phenyl)methylene]-1-methylpyrimidine-2,4,6-trione (2 i).
125, 125, 124, 124, 119, 113, 111, and 79 ppm.
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(4-hydroxy-
phenyl)methylene]-1-methylpyrimidine-2,4,6-trione (2o).
This compound was prepared in 81% isolated yield by follow-
1
ing General Procedure E. H-NMR (DMSO-d , 500 MHz) δ
6
11.32 (1H, s), 11.01 (2H, s), 8.83 (1H, d, J=2.7 Hz), 8.33 (1H, d,
J=6.0 Hz), 8.05 (1H, d, J=9.6 Hz), 7.73 (2H, d, J=8.7 Hz), 6.93
This compound was prepared in 84% isolated yield by follow-
1
ing General Procedure E. H-NMR (DMSO-d , 500 MHz): δ
6
11.40 (1H, s), 10.34(1H, s), 8.85 (1H, d J=3.0 Hz), 8.33 (1H, d,
13
(2H, d, J=9.0 Hz), and 3.76 ppm (3H, s). C-NMR (DMSO-d ,
6
500 MHz) δ 163, 158, 157, 147, 140, 133, 126, 125, 125, 119,
113, 110, 109, 78, and 51 ppm.
J =12.5 Hz, J =3.0 Hz), 7.99 (1H, d, J=9.5 Hz), 7.61 (2H, d,
1 2
13
J=8.5 Hz), and 6.75 ppm (2H, d, J=8.5 Hz); C-NMR (DMSO-
d , 500 MHz): δ 158, 157, 155, 153, 149, 140, 132, 126, 126,
6
125, 124, 119, 112, 111, and 78, 24 ppm.
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(3-hydroxy-
phenyl)methylene]-1-methylpyrimidine-2,4,6-trione (2j).
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(4-hydroxy-
phenyl)methylene]-1,3-dimethylpyrimidine-2,4,6-trione (2p).
This compound was prepared in 88% isolated yield by following
1
General Procedure E. H-NMR (DMSO-d , 500 MHz): δ 11.37
6
(1H, s), 10.76 (2H, s), 8.87 (1H, d, J=2.1 Hz), 8.41 (1H, d, J=12.0
This compound was prepared in 91% isolated yield by following
1
General Procedure E. H-NMR (DMSO-d , 500 MHz): δ 11.40
Hz), 8.06 (1H, d, J=9.5 Hz), 7.24 (1H, t, J=7.5 Hz), 7.17 (2H, d),
13
6
and 6.79 ppm (1H, d, J=10.0 Hz): C-NMR (DMSO-d , 500
MHz): δ 158, 153, 148, 147, 140, 135, 133, 126, 125, 125, 119,
(1H, s), 10.35 (1H, s), 8.34 (1H, d of d, J =16 Hz, J =4 Hz), 8.00
1 2
6
(1H, d, J=16 Hz), 7.61(2H, d of d, J =11 Hz, J =4 Hz), and 6.70
1 2
13
114, 113, 112, 110, and 78 ppm.
ppm (2H, d of d, J =11 Hz, J =3 Hz); C-NMR (DMSO-d , 500
1 2 6
MHz): δ 157.1, 155.6, 153.7, 149.1, 140.4, 132.5, 126.3, 126.2,
Preparation of 5-[[N'-(2,4-Dinitrophenyl)hydrazino]-(4-hydrox-
yphenyl)methylene]-1-methylpyrimidine-2,4,6-trione (2k).
125.2, 124.9, 120.0, 113.0, 111.4, 78.2, and 23.8 ppm.
Preparation of 5-[[(2,4-Dinitrophenyl)hydrazono]-(4-nitro-
phenyl)methyl]pyrimidine-2,4,6-trione (2r).
This compound was prepared in 88% isolated yield by follow-
1
ing General Procedure E. H-NMR (DMSO-d , 500 MHz): δ
6
11.44 (1H, s), 10.34 (1H, s), 8.86 (1H, d, J=1.5 Hz), 8.33 (1H, d,
J=6.0 Hz), 8.04 (1H, d, J=4.5 Hz), 7.60 (2H, d, J=4.0 Hz), 6.75
To a 250 mL round bottom flask charged with 20 mL propanol,
5(4-nitro-benzoyl)-pyrimidine-2,4,6-trione (1 b) (0.277 g; 1.00