698
D.-Q. Shi, S.-N. Ni, F. Yang, J.-W. Shi, G.-L. Dou, X.-Y. Li, X.-S. Wang, S.-J. Ji
Vol 45
5-(2-Chlorophenyl)-1,3,8,8-tetramethyl-7,8,9,10-tetrahy-
for C20H20BrN3O3: C, 55.83; H, 4.68; N, 9.77. Found: C, 55.95;
H, 4.64; N, 9.82.
dropyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4i).
This compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3222, 3093, 2959, 1702, 1661, 1632,
1606, 1493, 1438, 1379, 1359, 1288, 1244, 1210, 1150, 1128,
5-(4-Chlorophenyl)-1,8,8-trimethyl-7,8,9,10-tetrahydropy-
rimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4n). This
compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3276, 3219, 3092, 2968, 2890, 1742,
1663, 1639, 1617, 1490, 1383, 1355, 1278, 1237, 1213, 1169,
1153, 1086, 1012, 879, 850, 834, 751 cm-1; 1H nmr (DMSO-d6):
δ 0.87 (s, 3H, CH3), 1.04 (s, 3H, CH3), 2.04 (d, J = 16.0 Hz, 1H,
CH), 2.22 (d, J = 16.0 Hz, 1H, CH), 2.53 (d, J = 17.6 Hz, 1H,
CH), 2.60 (d, J = 17.6 Hz, 1H, CH), 3.38 (s, 3H, CH3N), 4.82 (s,
1H, CH), 7.22 (d, J = 8.8 Hz, 2H, ArH), 7.25 (d, J = 8.8 Hz, 2H,
ArH), 8.99 (br., s, 1H, NH), 11.03 (br., s, 1H, NH). Anal. Calcd.
for C20H20ClN3O3: C, 62.26; H, 5.22; N, 10.89. Found: C, 62.27;
H, 5.16; N, 10.94.
5-(2,4-Dichlorophenyl)-1,8,8-trimethyl-7,8,9,10-tetrahy-
dropyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4o).
This compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3279, 3201, 3087, 2960, 1718, 1676,
1649, 1632, 1585, 1496, 1381, 1357, 1281, 1236, 1214, 1151,
1103, 1064, 1046, 846, 757 cm-1; 1H nmr (DMSO-d6): δ 0.89 (s,
3H, CH3), 1.03 (s, 3H, CH3), 1.98 (d, J = 16.0 Hz, 1H, CH), 2.20
(d, J = 16.0 Hz, 1H, CH), 2.53 (d, J = 17.6 Hz, 2H, CH2), 3.38
(s, 3H, CH3N), 5.09 (s, 1H, CH), 7.26 (dd, J1 = 2.0 Hz, J2 = 8.4
Hz, 1H, ArH), 7.33 (d, J = 8.4 Hz, 1H, ArH), 7.35 (d, J = 2.0
Hz, 1H, ArH), 8.98 (br., s, 1H, NH), 10.96 (br., s, 1H, NH).
Anal. Calcd. for C20H19Cl2N3O3: C, 57.15; H, 4.56; N, 10.00.
Found: C, 57.32; H, 4.51; N, 10.12.
1
1080, 1050, 962, 836, 769, 752 cm-1; H nmr (DMSO-d6): δ
0.88 (s, 3H, CH3), 1.03 (s, 3H, CH3), 1.97 (d, J = 16.0 Hz, 1H,
CH), 2.19 (d, J = 16.0 Hz, 1H, CH), 2.58 (d, J = 17.2 Hz, 2H,
CH2), 3.04 (s, 3H, CH3N), 3.45 (s, 3H, CH3N), 5.16 (s, 1H,
CH), 7.05-7.10 (m, 1H, ArH), 7.14-7.22 (m, 2H, ArH), 7.33
(d, J = 7.6 Hz, 1H, ArH), 9.02 (br., s, 1H, NH). Anal. Calcd.
for C21 H21ClN3O3: C, 63.08; H, 5.55; N, 10.51. Found: C,
63.17; H, 5.42; N, 10.64.
1,3,8,8-Tetramethyl-5-(thiophen-2-yl)-7,8,9,10-tetrahydro-
pyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4j). This
compound was obtained as solid with mp 295-296 ºC; ir
(potassium bromide): 3299, 3239, 2961, 2944, 2869, 1702,
1661, 1640, 1614, 1494, 1437, 1380, 1359, 1342, 1280, 1247,
1210, 1202, 1148, 1071, 1051, 1035, 959, 873, 841, 811, 784,
753, 715 cm-1; 1H nmr (DMSO-d6): δ 0.97 (s, 3H, CH3), 1.06 (s,
3H, CH3), 2.14 (d, J = 16.4 Hz, 1H, CH), 2.27 (d, J = 16.4 Hz,
1H, CH), 2.57 (d, J = 16.4 Hz, 1H, CH), 2.61 (d, J = 16.4 Hz,
1H, CH), 3.15 (s, 3H, CH3N), 3.41 (s, 3H, CH3N), 5.20 (s, 1H,
CH), 6.75-6.83 (m, 2H, ArH), 7.17-7.21 (m, 1H, ArH), 9.19 (br.,
s, 1H, NH). Anal. Calcd. for C19H21N3O3S: C, 61.44; H, 5.70; N,
11.31. Found: C, 61.63; H, 5.60; N, 11.47.
5-(4-Methoxyphenyl)-1,8,8-trimethyl-7,8,9,10-tetrahydro-
pyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4k). This
compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3278, 3218, 3092, 2968, 2832, 1721,
1654, 1644, 1492, 1420, 1383, 1356, 1284, 1237, 1213, 1171,
5-(4-Fluorophenyl)-1,8,8-trimethyl-7,8,9,10-tetrahydro-
pyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4p). This
compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3282, 3224, 3095, 3017, 2962, 2889,
1724, 1661, 1646, 1617, 1491, 1420, 1384, 1344, 1282, 1218,
1
1154, 1104, 1039, 879, 838, 747 cm-1; H nmr (DMSO-d6): δ
0.89 (s, 3H, CH3), 1.04 (s, 3H, CH3), 2.04 (d, J = 16.0 Hz, 1H,
CH), 2.21 (d, J = 16.0 Hz, 1H, CH), 2.52 (d, J = 17.2 Hz, 1H,
CH), 2.59 (d, J = 17.2 Hz, 1H, CH), 3.36 (s, 3H, CH3N), 3.67 (s,
3H, CH3O), 4.77 (s, 1H, CH), 6.74 (d, J = 8.4 Hz, 2H, ArH),
7.11 (d, J = 8.4 Hz, 2H, ArH), 8.92 (br., s, 1H, NH), 10.98 (br.,
s, 1H, NH). Anal. Calcd. for C21H23N3O4: C, 66.13; H, 6.08; N,
11.02. Found: C, 66.27; H, 6.02; N, 11.19.
1,8,8-Trimethyl-5-p-tolyl-7,8,9,10-tetrahydropyrimido[4,5-
b]quinoline-2,4,6(1H,3H,5H)-trione (4l). This compound was
obtained as solid with mp > 300 ºC; ir (potassium bromide):
3276, 3218, 3092, 2970, 2888, 1724, 1663, 1647, 1620, 1491,
1383, 1345, 1281, 1237, 1211, 1169, 1154, 1105, 1064, 880,
848, 830 cm-1; 1H nmr (DMSO-d6): δ 0.88 (s, 3H, CH3), 1.04 (s,
3H, CH3), 2.03 (d, J = 16.0 Hz, 1H, CH), 2.19 (s, 3H, CH3), 2.21
(d, J = 16.0 Hz, 1H, CH), 2.52 (d, J = 17.6 Hz, 1H, CH), 2.59 (d,
J = 17.6 Hz, 1H, CH), 3.37 (s, 3H, CH3N), 4.79 (s, 1H, CH),
6.98 (d, J = 8.0 Hz, 2H, ArH), 7.08 (d, J = 8.0 Hz, 2H, ArH),
8.93 (br., s, 1H, NH), 10.98 (br., s, 1H, NH). Anal. Calcd. for
C21H23N3O3: C, 69.02; H, 6.34; N, 11.50. Found: C, 69.18; H,
6.29; N, 11.63.
5-(4-Bromophenyl)-1,8,8-trimethyl-7,8,9,10-tetrahydropyr-
imido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4m). This
compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3279, 3220, 3092, 2966, 2889, 1724,
1661, 1645, 1614, 1490, 1382, 1355, 1277, 1238, 1212, 1169,
1153, 1067, 1008, 879, 849, 833, 750 cm-1; 1H nmr (DMSO-d6):
δ 0.87 (s, 3H, CH3), 1.04 (s, 3H, CH3), 2.04 (d, J = 16.0 Hz, 1H,
CH), 2.22 (d, J = 16.0 Hz, 1H, CH), 2.52 (d, J = 17.2 Hz, 1H,
CH), 2.60 (d, J = 17.2 Hz, 1H, CH), 3.37 (s, 3H, CH3N), 4.80 (s,
1H, CH), 7.17 (d, J = 8.4 Hz, 2H, ArH), 7.38 (d, J = 8.4 Hz, 2H,
ArH), 8.98 (br., s, 1H, NH), 11.03 (br., s, 1H, NH). Anal. Calcd.
1
1154, 1112, 1066, 846, 753, 713 cm-1; H nmr (DMSO-d6): δ
0.87 (s, 3H, CH3), 1.04 (s, 3H, CH3), 2.05 (d, J = 16.0 Hz, 1H,
CH), 2.22 (d, J = 16.0 Hz, 1H, CH), 2.53 (d, J = 17.2 Hz, 1H,
CH), 2.60 (d, J = 17.2 Hz, 1H, CH), 3.38 (s, 3H, CH3N), 4.83 (s,
1H, CH), 6.98-7.03 (m, 2H, ArH), 7.21-7.24 (m, 2H, ArH), 8.98
(br., s, 1H, NH), 11.02 (br., s, 1H, NH). Anal. Calcd. for
C20H20FN3 O3: C, 65.03; H, 5.46; N, 11.38. Found: C, 65.16; H,
5.51; N, 11.32.
5-(2-Methoxyphenyl)-1,8,8-trimethyl-7,8,9,10-tetrahydro-
pyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H)-trione (4q). This
compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3238, 3209, 3088, 2952, 2834, 1714,
1648, 1617, 1499, 1383, 1358, 1286, 1250, 1235, 1198, 1158,
1
1119, 1029, 856, 789, 757 cm-1; H nmr (DMSO-d6): δ 0.83 (s,
3H, CH3), 1.03 (s, 3H, CH3), 1.93 (d, J = 16.4 Hz, 1H, CH), 2.17
(d, J = 16.4 Hz, 1H, CH), 2.48 (d, J = 17.2 Hz, 1H, CH), 2.53 (d,
J = 17.2 Hz, 1H, CH), 3.38 (s, 3H, CH3N), 3.68 (s, 3H, CH3O),
4.89 (s, 1H, CH), 6.75-6.78 (m, 1H, ArH), 6.84 (d, J = 8.0 Hz,
1H, ArH), 7.04-7.08 (m, 1H, ArH), 7.20 (dd, J1 = 1.6 Hz, J2 =
7.2 Hz, 1H, ArH), 8.89 (br., s, 1H, NH), 10.84 (br., s, 1H, NH).
Anal. Calcd. for C21H23N3O4: C, 66.13; H, 6.08; N, 11.02.
Found: C, 66.25; H, 6.21; N, 11.09.
5-(3,4-Methylidenedioxyphenyl)-1,8,8-trimethyl-7,8,9,10-
tetrahydropyrimido[4,5-b]quinoline-2,4,6(1H,3H, 5H)-trione
(4r). This compound was obtained as solid with mp > 300 ºC; ir
(potassium bromide): 3296, 3164, 3058, 2953, 2804, 1720,
1691, 1671, 1641, 1625, 1495, 1439, 1415, 1367, 1357, 1246,
1212, 1169, 1151, 1104, 1036, 927, 857, 794, 778, 759 cm-1; 1H
nmr (DMSO-d6): δ 0.90 (s, 3H, CH3), 1.04 (s, 3H, CH3), 2.06 (d,
J = 16.0 Hz, 1H, CH), 2.21 (d, J = 16.0 Hz, 1H, CH), 2.52 (d, J