96 B. Janardhan et al.
3,4,5,6-Tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-
8-methoxybenzo[h]quinazolin-2(1H)-one (4j) This compound
was obtained from 1, 2j and 3a as a pale yellow solid within 30 min;
yield 0.32 g (91%); mp 271–273°C; IR: 3417, 3386, 3219, 3124,
(94%); mp 253–255°C; IR: 3190, 2922, 2831, 1682, 1192, 1133,
1
1084 cm-1; H NMR (CDCl3): δ 1.93 (m, 1H), 2.06 (m, 1H), 2.72
(m, 2H), 3.81 (s, 3H), 3.86 (s, 3H), 3.88 (s, 3H), 5.04 (s, 1H), 6.80
(m, 6H), 7.16 (d, J = 6.6 Hz, 1H), 7.66 (s, 1H); 13C NMR (CDCl3):
174.2, 158.8, 149.7, 147.9, 137.5, 137.1, 126.5, 123.0, 120.5, 120.3,
115.2, 113.7, 112.2, 110.8, 107.9, 58.0, 55.2, 54.2, 27.7, 23.5;
MS: m/z 382 (M+). Anal. calcd for C21H22N2O3S: C, 65.95; H, 5.80;
N, 7.32. Found: C, 65.73; H, 5.91; N, 7.09.
1
2946, 2810, 1698, 1247, 1167 cm-1; H NMR (CDCl3): δ 1.80 (m,
1H), 2.14 (m, 1H), 2.58 (m, 1H), 2.69 (m, 1H), 3.76 (s, 3H), 3.80 (s,
3H), 4.95 (s, 1H), 7.01 (m, 6H), 8.00 (s, 1H), 8.31 (s, 1H), 8.99 (s,
1H); 13C NMR (CDCl3): 158.8, 155.1, 151.2, 143.3, 138.7, 137.4,
127.7, 122.4, 121.5, 120.8, 116.7, 113.7, 112.5, 110.8, 104.9, 58.6,
56.4, 55.3, 27.9, 24.1; MS: m/z 352 (M+).Anal. calcd for C20H20N2O4:
C, 68.17; H, 5.72; N, 7.95. Found: C, 68.33; H, 5.64; N, 8.07.
3,4,5,6-Tetrahydro-8-methoxy-4-p-tolylbenzo[h]quinazoline-
2(1H)-thione (4p) This compound was obtained from 1, 2f and
3b as a pale yellow solid within 35 min; yield 0.29 g (86%); mp
248–251°C; IR: 3197, 2983, 2931, 1674, 1188, 1136 cm-1; 1H NMR
(CDCl3): δ 1.93 (m, 1H), 2.07 (m, 1H), 2.41 (s, 3H), 2.70 (m, 2H),
3.81 (s, 3H), 5.03 (s, 1H), 6.67 (m, 3H), 7.12 (d, J = 6.6 Hz, 2H),
7.37 (m, 3H), 8.98 (s, 1H); 13C NMR (CDCl3): 174.7, 159.3, 140.8,
138.1, 136.5, 129.0, 127.1, 126.9, 124.1, 121.4, 114.2, 111.2, 108.3,
58.2, 55.3, 27.9, 25.3, 23.7; MS: m/z 336 (M+). Anal. calcd for
C20H20N2OS: C, 71.40; H, 5.99; N, 8.33. Found: C, 71.16; H, 6.32;
N, 8.52.
3,4,5,6-Tetrahydro-8-methoxy-4-phenylbenzo[h]quinazoline-
2(1H)-thione (4k) This compound was obtained from 1, 2a and
3b as a white solid within 25 min; yield 0.30 g (93%); mp 272–
274°C; IR: 3379, 3161, 2968, 1672, 1564, 1197, 1136 cm-1; 1H
NMR (CDCl3): δ 1.81 (m, 1H), 2.10 (m, 1H), 2.65 (m, 2H), 3.76 (s,
3H), 5.01 (s, 1H), 6.67 (m, 4H), 7.10 (d, J = 6.3 Hz, 2H), 7.36 (m,
3H), 9.02 (s, 1H); 13C NMR (CDCl3): 174.3, 159.0, 143.8, 137.5,
128.7, 127.2, 126.9, 126.8, 123.0, 120.5, 113.9, 110.9, 107.8, 57.8,
55.2, 27.6, 23.5; MS: m/z 322 (M+). Anal. calcd for C19H18N2OS:
C, 70.78; H, 5.63; N, 8.69. Found: C, 70.54; H, 5.81; N, 8.87.
3,4,5,6-Tetrahydro-4-(4-hydroxyphenyl)-8-methoxybenzo[h]
quinazoline-2(1H)-thione (4q) This compound was obtained
from 1, 2g and 3b as a pale yellow solid within 30 min; yield 0.32
g (95%); mp 268–270°C; IR: 3412, 3173, 2925, 2812, 1656, 1167,
1055 cm-1; 1H NMR (CDCl3 + DMSO-d6): δ 1.94 (m, 1H), 2.06
(m, 1H), 2.69 (m, 2H), 3.80 (s, 3H), 4.92 (s, 1H), 6.77 (m, 4H), 7.15
(d, J = 6.3 Hz, 2H), 7.32 (d, J = 6.3 Hz, 1H), 8.01 (s, 1H), 8.31 (s,
1H), 8.98 (s, 1H); 13C NMR (CDCl3 + DMSO-d6): 174.2, 158.8, 156.6,
137.8, 136.4, 128.6, 126.5, 123.3, 120.4, 115.8, 114.0, 110.8, 108.2, 57.8,
55.3, 27.6, 23.6; MS: m/z 339 (M+1). Anal. calcd for C19H18N2O2S:
C, 67.43; H, 5.36; N, 8.28. Found: C, 67.21; H, 5.48; N, 8.64.
4-(2-Chlorophenyl)-3,4,5,6-tetrahydro-8-methoxybenzo[h]qui-
nazoline-2(1H)-thione (4l) This compound was obtained from 1,
2b and 3b as a white solid within 25 min; yield 0.33 g (93%); mp 270–
272°C; IR: 3196, 2928, 2845, 1675, 1180, 1085, 732 cm-1; 1H NMR
(CDCl3): δ 1.80 (m, 1H), 2.16 (m, 1H), 2.66 (m, 2H), 3.81 (s, 3H),
4.96 (s, 1H), 6.74 (m, 4H), 7.13 (d, J = 6.3 Hz, 2H), 7.44 (m, 2H), 8.98
(s, 1H); 13C NMR (CDCl3): 174.1, 158.7, 142.0, 138.2, 132.5, 128.7,
128.5, 128.3, 126.8, 126.7, 123.5, 120.7, 113.9, 110.8, 108.1, 56.1,
55.0, 27.5, 23.7; MS: m/z 356 (M+). Anal. calcd for C19H17ClN2OS: C,
63.95; H, 4.80; N, 7.85. Found: C, 63.57; H, 4.93; N, 7.99.
3,4,5,6-Tetrahydro-8-methoxy-4-(3-nitrophenyl)benzo[h]qui-
nazoline-2(1H)-thione (4r) This compound was obtained from
1, 2h and 3b as a yellow solid within 20 min; yield 0.33 g (90%);
mp 244–246°C; IR: 3186, 2972, 2935, 1674, 1566, 1195, 1018 cm-1;
1H NMR (CDCl3): δ 1.90 (m, 1H), 2.14 (m, 1H), 2.64 (m, 2H), 3.80
(s, 3H), 4.99 (s, 1H), 7.09 (m, 4H), 7.74 (m, 2H), 8.13 (d, J = 6.3 Hz,
2H), 8.61 (s, 1H); 13C NMR (CDCl3): 175.0, 159.2, 148.3, 144.7,
139.1, 133.3, 129.6, 127.4, 124.1, 122.4, 120.9, 119.2, 114.5, 111.8,
108.5, 56.7, 55.6, 27.7, 24.2; MS: m/z 368 (M++1). Anal. calcd for
C19H17N3O3S: C, 62.11; H, 4.66; N, 11.44. Found: C, 61.87; H, 4.75;
N, 11.63.
4-(4-Chlorophenyl)-3,4,5,6-tetrahydro-8-methoxybenzo[h]
quinazoline-2(1H)-thione (4m) This compound was obtained
from 1, 2c and 3b as a yellow solid within 10 min; yield 0.34 g
(95%); mp 240–243°C; IR: 3198, 2928, 2830, 1677, 1187, 1087, 741
cm-1; 1H NMR (DMSO-d6): δ 1.81 (m, 1H), 2.15 (m, 1H), 2.60 (m,
2H), 3.74 (s, 3H), 4.95 (s, 1H), 6.76 (s, 2H), 7.32 (d, J = 6.3 Hz, 2H),
7.45 (d, J = 6.3 Hz, 2H), 7.63 (d, J = 6.9 Hz, 1H), 9.05 (s, 1H), 9.71
(s, 1H); 13C NMR (DMSO-d6): 174.2, 158.9, 141.9, 137.5, 132.4,
128.8, 128.6, 126.7, 123.1, 120.4, 113.9, 110.8, 107.9, 57.7, 55.1,
27.6, 23.4; MS: m/z 357 (M++1). Anal. calcd for C19H17ClN2OS:
C, 63.95; H, 4.80; N, 7.85. Found: C, 63.71; H, 4.67; N, 7.92.
4-(4-(Dimethylamino)phenyl)-3,4,5,6-tetrahydro-8-
methoxybenzo[h]quinazoline-2(1H)-thione (4s) This com-
pound was obtained from 1, 2i and 3b as a yellow solid within
30 min; yield 0.33 g (90%); mp 274–276°C; IR: 3387, 3190, 2918,
3,4,5,6-Tetrahydro-8-methoxy-4-(4-methoxyphenyl)benzo[h]
quinazoline-2(1H)-thione(4n) Thiscompoundwasobtainedfrom
1, 2d and 3b as a yellow solid within 30 min; yield 0.32 g (91%); mp
234–237°C [Literature (El-Baih et al., 2005) mp 236–237°C]; IR:
3192, 2920, 2824, 1671, 1173, 1124, 1082 cm-1; 1H NMR (CDCl3): δ
1.91 (m, 1H), 2.06 (m, 1H), 2.71 (m, 2H), 3.80 (s, 6H), 5.03 (s, 1H),
6.56 (s, 1H), 6.77 (m, 2H), 6.88 (d, J = 6.3 Hz, 2H), 7.14 (d, J = 6.3
Hz, 1H), 7.25 (d, J = 6.6 Hz, 2H), 7.63 (s, 1H); 13C NMR (CDCl3):
174.2, 159.9, 159.7, 137.8, 133.5, 128.7, 125.6, 120.5, 120.2, 114.8,
114.4, 111.0, 108.0, 60.2, 55.3, 28.2, 23.5; MS: m/z 352 (M+). Anal.
calcd for C20H20N2O2S: C, 68.16; H, 5.72; N, 7.95. Found: C, 67.82;
H, 5.86; N, 8.14.
1
2845, 1669, 1178, 1123, 1087 cm-1; H NMR (CDCl3): δ 1.94 (m,
1H), 2.15 (m, 1H), 2.65 (m, 2H), 3.07 (s, 6H), 3.87 (s, 3H), 4.96 (s,
1H), 6.81 (m, 4H), 7.21 (m, 2H), 7.37 (d, J = 6.3 Hz, 2H), 8.47 (s,
1H); 13C NMR (CDCl3): 174.2, 158.9, 147.7, 137.5, 133.3, 128.1,
126.7, 123.1, 120.4, 114.2, 113.9, 110.8, 107.9, 57.7, 55.1, 42.2,
27.6, 23.4; MS: m/z 365 (M+). Anal. calcd for C21H23N3OS: C, 69.01;
H, 6.34; N, 11.50. Found: C, 69.39; H, 6.02; N, 11.68.
3,4,5,6-Tetrahydro-4-(4-hydroxy-3-methoxyphenyl)-8-
methoxybenzo[h]quinazoline-2(1H)-thione (4t) This com-
pound was obtained from 1, 2j and 3b as a pale yellow solid within
35 min; yield 0.32 g (87%); mp 264–266°C; IR: 3422, 3179, 2924,
2846, 1698, 1187, 1145, 1087 cm-1; 1H NMR (CDCl3): δ 1.93 (m, 1H),
3,4,5,6-Tetrahydro-8-methoxy-4-(3,4-dimethoxyphenyl)
benzo[h]quinazoline-2(1H)-thione (4o) This compound was ob-
tained from 1, 2e and 3b as a white solid within 40 min; yield 0.36 g
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