PAPER
Synthesis of New Dihydropyrimido[4,5-b]quinolinetrione Derivatives
991
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.3, 32.0, 40.0, 42.1,
48.1 52.9, 57.6, 80.2, 109.9, 126.8, 145.1, 150.2, 152.1, 161.1,
163.2, 168.9, 169.9, 194.3.
1,4-Bis[10-(4-methoxyphenyl)-8,8-dimethyl-8,9-dihydropyrim-
ido[4,5-b]quinoline-2,4,6(1H,3H,5H,7H,10H)-trione]benzene
(5j)
Yield: 85%; yellow solid; >300 °C (dec.).
IR (KBr): 3210, 1732, 1674, 1565 cm–1.
Anal. Calcd for C22H27N5O2S (425.55): C, 62.09; H, 6.40; N, 16.46.
Found: C, 62.06; H, 6.38; N, 16.45.
1H NMR (250 MHz, DMSO-d6/TMS): d = 0.97 (s, 3 H), 1.10 (s, 3
H), 2.48 (m, 4 H), 3.77 (s, 3 H), 5.06 (s, 1 H), 7.02 (d, J = 3.2 Hz, 2
H), 7.36 (d, J = 3.2 Hz, 2 H), 7.72 (d, J = 10.8 Hz, 2 H), 9.50 (s, 1
H), 10.35 (s, 1 H).
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.2, 33.2, 52.5, 56.5,
81.2, 110.0, 115.3, 117.2, 126.1, 132.4, 133.6, 143.1, 150.1, 152.1,
153.7, 162.9, 192.5.
10-(4-Chlorophenyl)-5-(1H-indol-3-yl)-8,8-dimethyl-8,9-dihy-
dropyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H,7H,10H)-trione
(5f)
Yield: 92%; yellow color; mp 275–277 °C.
IR (KBr): 3290, 3220, 1742, 1660, 1560 cm–1.
1H NMR (250 MHz, DMSO-d6/TMS): d = 1.00 (s, 6 H), 2.35–2.50
(m, 4 H), 5.30 (s, 1 H), 7.17 (d, J = 8.8 Hz, 2 H), 7.31–7.41 (m, 3
H), 7.57–7.61 (m, 2 H), 7.87–7.90 (m, 2 H), 12.18 (s, 1 H), 12.22 (s,
1 H), 12.92 (s, 1 H).
Anal. Calcd for C46H44N6O8 (808.88): C, 68.30; H, 5.48; N, 10.39.
Found: C, 68.25; H, 5.44; N, 10.36.
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.8, 32.2, 50.0, 97.1,
108.7, 112.3, 113.3, 117.8, 123.1, 124.0, 124.2, 129.1, 136.6, 141.0,
144.5, 160.9, 162.7, 177.6.
10-(4-Methoxyphenyl)-8,8-dimethyl-5-(3-nitrophenyl)-8,9-di-
hydropyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H,7H,10H)-tri-
one (5k)
Yield: 93%; yellow color; mp 257–259 °C.
IR (KBr): 3215, 3095, 1732, 1674, 1565, 1520, 1330, 850 cm–1.
Anal. Calcd for C27H23ClN4O3 (486.95): C, 66.60; H, 4.76; N,
11.51. Found: C, 66.57; H, 4.71; N, 11.47.
1H NMR (250 MHz, DMSO-d6/TMS): d = 0.87 (s, 3 H), 1.01 (s, 3
H), 2.24–2.49 (m, 4 H), 3.71 (s, 3 H), 6.04 (s, 1 H), 6.96–7.00 (m, 2
H), 7.21–7.25 (m, 2 H), 7.49 (t, J = 3.9 Hz, 1 H), 7.80 (s, 1 H), 7.92
(m, 2 H), 10.19 (s, 1 H), 11.11 (s, 1 H).
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.5, 30.6, 50.1, 55.4,
90.2, 114.8, 119.8, 121.0, 123.9, 124.7, 129.0, 129.6, 133.7, 147.5,
147.7, 150.6, 158.4, 178.3, 200.9.
10-(1H-Benzo[d]imidazol-2-yl)-5-[4-(dimethylamino)phenyl]-
8,8-dimethyl-2-thioxo-2,3,8,9-tetrahydropyrimido[4,5-b]quino-
line-4,6(1H,5H,7H,10H)-dione (5g)
Yield: 85%; violet solid; mp 233–235 °C.
IR (KBr): 3300, 3217, 1751, 1655, 1557 cm–1.
1H NMR (250 MHz, DMSO-d6/TMS): d = 0.93 (s, 3 H), 1.00 (s, 3
H), 2.77–2.85 (m, 4 H), 3.13 (s, 6 H), 5.87 (s, 1 H), 6.54 (t, J = 4.4
Hz, 2 H), 6.77 (t, J = 9.2 Hz, 2 H), 7.10–7.20 (m, 2 H), 7.32–7.37
(m, 2 H), 12.02 (s, 1 H), 12.12 (s, 1 H), 13.13 (s, 1 H).
Anal. Calcd for C26H24N4O6 (488.49): C, 63.93; H, 4.95; N, 11.47.
Found: C, 63.90; H, 4.91; N, 11.43.
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.2, 32.3, 51.1, 80.0,
104.2, 110.1, 115.0, 117.9, 121.9, 126.2, 136.1, 139.1, 141.1, 144.4,
149.9, 151.7, 162.8, 192.6.
8,8-Dimethyl-10-[2-(piperazin-1-yl)ethyl]-5-(thiophen-2-yl)-
8,9-dihydropyrimido[4,5-b]quinoline-
2,4,6(1H,3H,5H,7H,10H)-trione (5l)
Yield: 95%; yellow color; mp 218–220 °C.
IR (KBr): 3332, 3204, 1731, 1676, 1568, 1235 cm–1.
Anal. Calcd for C28H28N6O2S (512.63): C, 65.60; H, 5.51; N, 16.39.
Found: C, 65.56; H, 5.48; N, 16.36.
1H NMR (250 MHz, DMSO-d6/TMS): d = 0.94 (s, 3 H), 1.08 (s, 3
H), 1.85 (s, 1 H), 2.40–2.55 (m, 4 H), 2.85–2.89 (m, 4 H), 3.15–3.23
(m, 6 H), 3.52–3.71 (m, 2 H), 4.65 (s, 1 H), 7.27 (q, J = 12.2, 2.9 Hz,
1 H), 7.32 (d, J = 1.6 Hz, 1 H) 7.55 (d, J = 2.1 Hz, 1 H), 9.98 (s, 1
H), 10.61 (s, 1 H).
8,8-Dimethyl-5-phenyl-8,9-dihydropyrimido[4,5-b]quinoline-
2,4,6(1H,3H,5H,7H,10H)-trione (5h)
Yield: 85%; white solid; mp 210–212 °C.
IR (KBr): 3320, 3280, 1754, 1649, 1552 cm–1.
1H NMR (250 MHz, DMSO-d6/TMS): d = 1.00 (s, 6 H), 2.40–2.61
(m, 4 H), 4.67 (s, 1 H), 7.26–7.33 (m, 3 H), 7.57–7.60 (m, 2 H),
10.21 (s, 1 H), 10.40 (s, 1 H), 12.01 (s, 1 H).
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.1, 31.0, 33.4, 47.4,
52.1, 55.1, 84.9, 111.2, 121.4, 126.2, 140.2, 150.2, 152.6, 158.3,
162.6, 175.1.
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.2, 31.2, 51.9, 81.2,
110.3, 126.0, 129.2, 141.8, 150.5, 180.3.
Anal. Calcd for C23H29N5O3S (455.57): C, 60.64; H, 6.42; N, 15.37.
Found: C, 60.61; H, 6.38; N, 15.32.
Anal. Calcd for C19H19N3O3 (337.37): C, 67.64; H, 5.68; N, 12.46.
Found: C, 67.61; H, 5.65; N, 12.42.
10-{9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tet-
rahydrofuran-2-yl]-9H-purin-6-yl}-5-(1H-indol-2-yl)-8,8-di-
methyl-8,9-dihydropyrimido[4,5-b]quinoline-
2,4,6(1H,3H,5H,7H,10H)-trione (5m)
Yield: 73%; yellow solid; mp 260–262 °C.
IR (KBr): 3540, 3330, 3212, 1728, 1672, 1565 cm–1.
10-(4-Iodophenyl)-8,8-dimethyl-5-(4-nitrophenyl)-8,9-dihydro-
pyrimido[4,5-b]quinoline-2,4,6(1H,3H,5H,7H,10H)-trione (5i)
Yield: 89%; yellow solid; mp 281–283 °C.
IR (KBr): 3212, 3090, 1730, 1677 1565, 1522, 1335, 853 cm–1.
1H NMR (250 MHz, DMSO-d6/TMS): d = 0.99 (s, 3 H), 1.02 (s, 3
H), 2.45–2.49 (m, 4 H), 2.57–2.59 (m, 3 H), 4.20 (d, J = 1.7 Hz, 1
H), 4.41 (d, J = 2.3 Hz, 1 H), 4.81 (d, J = 2.0 Hz, 1 H), 5.62 (d,
J = 1.9 Hz, 1 H), 6.30 (br s, 4 H), 7.31 (d, J = 3.2 Hz, 2 H), 7.56 (q,
J = 3.8, 3.0 Hz, 2 H), 7.85 (t, J = 1.5 Hz, 1 H), 7.86 (s, 1 H), 7.88 (s,
1 H), 11.02 (s, 1 H), 11.27 (s, 1 H), 12.70 (s, 1 H).
13C NMR (250 MHz, DMSO-d6/TMS): d = 27.7, 31.2, 53.1, 62.9,
74.0, 75.1, 82.9, 113.8, 116.6, 118.4, 122.9, 128.9, 134.3, 141.6,
145.0, 148.9, 155.6, 168.4, 169.8, 194.2.
1H NMR (250 MHz, DMSO-d6/TMS): d = 0.69 (s, 3 H), 0.87 (s, 3
H), 2.48 (m, 4 H), 5.10 (s, 1 H), 7.45 (d, J = 8.4 Hz, 2 H), 7.55 (d,
J = 8.5 Hz, 2 H), 7.76 (d, J = 8.2 Hz, 2 H), 8.00 (d, J = 7.0 Hz, 2 H),
10.21 (s, 1 H), 10.51 (s, 1 H).
13C NMR (250 MHz, DMSO-d6/TMS): d = 30.0, 33.1, 80.1, 85.1,
109.7, 120.9, 123.4, 121.4, 138.9, 141.2, 145.2, 147.2, 150.1, 153.5,
163.1, 185.5.
Anal. Calcd for C25H21IN4O5 (584.36): C, 51.38; H, 3.62; N, 9.59.
Found: C, 51.35; H, 3.59; N, 9.57.
Synthesis 2011, No. 6, 984–992 © Thieme Stuttgart · New York