6
MOHAMMADREZAEI ET AL.
1
3
NH) ppm; C NMR (100 MHz, CDCl ): δ 34.7 (CH),
3.2.6 | 16-(2-Bromophenyl)-4,16-dihydro-1H-benzo[a]
pyrimido[5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6f)
3
0
0
8
1
1
3.8, 117.2, 120.4, 121.2, 122.6, 124.7, 125.2, 127.3,
28.2, 129.0, 129.5, 129.9, 130.2, 130.4, 130.6, 132.4,
42.3, 142.9, 145.2, 146.8, 148.3, 152.4, 156.4 and 157.4
ꢀ
Brown powder; yield 0.424 g (81%), mp 231–233 C; IR
(KBr): νmax = 3270, 3115, 2825, 1692, 1634, 1583, 1552,
1483, 1452, 1402, 1335, 1211, 1149, 1023, 750 cm ; H
−
1 1
(
Colefinic and Carom), 159.7, 163.2 (2C=O) ppm; MS (m/z,
+
%
): 489 (M , 3); Anal. Calcd for C H N O : C, 66.26; H,
NMR (400 MHz, CDCl ): δ 5.29 (s, 1H, CH), 7.55–8.80
2
7
15
5
5
3
3
.09; N, 14.31%. Found: C, 66.42; H, 3.24; N, 14.17%.
(m, 11H, Ar-H), 9.36 (d, 1H, J = 8.0 Hz, Ar-H), 10.07 (s,
13
1
H, NH), 11.50 (s, 1H, NH) ppm; C NMR (100 MHz,
3
.2.3 | 16-(2-Chlorophenyl)-4,16-dihydro-1H-benzo[a]
CDCl ): δ 30.9 (CH), 82.6, 117.7, 122.6, 123.8, 124.0,
3
0
0
pyrimido[5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6c)
1
25.6, 125.9, 126.9, 127.0, 128.6, 129.3, 129.8, 130.0,
130.4, 131.7, 134.1, 142.4, 143.1, 146.2, 146.8, 147.0,
157.2 and 158.4 (Colefinic and C ), 159.5, 162.9 (2C=O)
ꢀ
Brown powder; yield 0.397 g (83%), mp 226–228 C; IR
KBr): νmax = 3185, 3030, 2895, 1709, 1633, 1585, 1524,
488, 1451, 1373, 1336, 1222, 1165, 1046, 752 cm ; H
(
1
arom
+
−1
1
ppm; MS (m/z, %): 523 (M , 5); Anal. Calcd for
NMR (400 MHz, CDCl ): δ 5.14 (s, 1H, CH), 7.27 (d, 1H,
C H BrN O : C, 61.97; H, 2.89; N, 10.71%. Found: C,
3
27 15
4 3
J = 8.0 Hz, Ar-H), 7.49 (d, 1H, J = 8.4 Hz, Ar-H),
62.14; H, 3.01; N, 10.57%.
7
1
.82–8.36 (m, 9H, Ar-H), 9.33–9.36 (m, 1H, Ar-H), 10.12 (s,
H, NH), 10.54 (s, 1H, NH) ppm; C NMR (100 MHz,
13
3.2.7
|
16-Phenyl-4,16-dihydro-1H-benzo[a]pyrimido
0
0
[
5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6g)
CDCl ): δ 32.8 (CH), 84.7, 117.5, 123.5, 125.3, 126.9, 127.3,
3
ꢀ
1
1
27.5, 128.2, 128.6, 129.1, 129.5, 129.8, 130.4, 130.7, 131.2,
42.2, 142.7, 146.8, 147.5, 150.3, 156.1 and 157.4 (Colefinic
Brown powder; yield 0.373 g (84%), mp 235–237 C; IR
(KBr): νmax = 3215, 3020, 2895, 1696, 1630, 1585, 1514,
−
1 1
and C ), 158.6, 163.9 (2C=O) ppm; MS (m/z, %):
4
3
1487, 1459, 1397, 1336, 1291, 1162, 1044, 752 cm ; H
arom
+
78 (M , 2); Anal. Calcd for C H ClN O : C, 67.72; H,
NMR (400 MHz, CDCl ): δ 5.31 (s, 1H, CH), 7.09 (d, 1H,
J = 8.0 Hz, Ar-H), 7.45–8.47 (m, 10H, Ar-H), 8.84 (d, 1H,
J = 7.2 Hz, Ar-H), 9.46 (d, 1H, J = 7.2 Hz, Ar-H), 10.11
s, 1H, NH), 10.52 (s, 1H, NH) ppm; C NMR (100 MHz,
CDCl ): δ 36.6 (CH), 85.8, 117.2, 122.6, 125.2, 127.4,
127.8, 128.5, 129.1, 129.3, 129.4, 129.6, 129.9, 130.0,
130.4, 131.6, 141.7, 142.4, 146.3, 146.8, 148.4, 157.1 and
158.3 (Colefinic and Carom), 160.5, 163.8 (2C=O) ppm; MS
2
7
15
4
3
3
.16; N, 11.70%. Found: C, 67.96; H, 3.37; N, 11.84%.
13
3
.2.4 | 16-(2,4-Dichlorophenyl)-4,16-dihydro-1H-benzo[a]
(
0
0
pyrimido[5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6d)
3
ꢀ
Brown powder; yield 0.426 g (83%), mp 245–247 C; IR
(KBr): νmax = 3175, 3045, 2915, 1721, 1681, 1583, 1527,
−
1 1
1
489, 1453, 1370, 1318, 1214, 1164, 1045, 750 cm ; H
+
NMR (400 MHz, CDCl ): δ 5.28 (s, 1H, CH), 7.40–8.75
(m/z, %): 444 (M , 14); Anal. Calcd for C H N O : C,
3
27 16 4 3
(
1
m, 10H, Ar-H), 9.50 (d, 1H, J = 8.0 Hz, Ar-H), 10.17 (s,
H, NH), 10.56 (s, 1H, NH) ppm; C NMR (100 MHz,
72.97; H, 3.63; N, 12.61%. Found: C, 72.68; H,
3.88; N, 12.50%.
1
3
CDCl ): δ 33.5 (CH), 84.4, 117.7, 123.9, 126.0, 126.5,
3
1
1
1
27.9, 128.4, 129.1, 129.3, 129.7, 130.2, 130.5, 131.4,
33.7, 135.4, 142.2, 142.8, 146.5, 146.9, 148.3, 154.1 and
3.2.8 | 16-(4-Methoxyphenyl)-4,16-dihydro-1H-benzo[a]
pyrimido[5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6h)
0
0
ꢀ
57.8 (Colefinic and Carom), 159.4, 163.7 (2C=O) ppm; MS
Red powder; yield 0.379 g (80%), mp 274–276 C; IR
+
(
m/z, %): 513 (M , 5); Anal. Calcd for C H Cl N O : C,
(KBr): νmax = 3175, 3045, 2900, 1718, 1665, 1588, 1535,
2
7
14
2 4 3
−1 1
6
2
3.17; H, 2.75; N, 10.91%. Found: C, 63.42; H,
.88; N, 11.09%.
1495, 1422, 1389, 1336, 1266, 1179, 1041, 746 cm ; H
NMR (400 MHz, CDCl ): δ 3.56 (s, 3H, OCH ), 5.20 (s,
3
3
1
1
H, CH), 6.63 (d, 1H, J = 8.8 Hz, Ar-H), 7.03–7.05 (m,
H, Ar-H), 7.78–8.42 (m, 9H, Ar-H), 9.06 (d, 1H,
3
.2.5 | 16-(4-Chloro-3-nitrophenyl)-4,16-dihydro-1H-benzo
0
0
[a]pyrimido[5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6e)
J = 7.6 Hz, Ar-H), 10.08 (s, 1H, NH), 10.47 (s, 1H, NH)
ppm; C NMR (100 MHz, CDCl ): δ 35.5 (CH), 55.3
ꢀ
13
Red powder; yield 0.439 g (84%), mp 235–236 C; IR
3
(
1
KBr): νmax = 3135, 3015, 2860, 1703, 1640, 1586, 1518,
491, 1459, 1377, 1338, 1212, 1162, 1043, 743 cm ; H
(OCH ), 82.5, 115.3, 117.8, 122.7, 124.1, 127.4, 128.7,
3
−
1 1
129.1, 129.3, 129.7, 130.4, 130.7, 130.9, 141.2, 142.1,
142.5, 146.5, 147.2, 155.8, 157.2 and 158.1 (Colefinic and
NMR (400 MHz, CDCl ): δ 5.42 (s, 1H, CH), 7.52–8.74
(
NH), 10.54 (s, 1H, NH) ppm; C NMR (100 MHz,
3
+
m, 10H, Ar-H), 9.34–9.36 (m, 1H, Ar-H), 10.15 (s, 1H,
Carom), 160.7, 164.2 (2C=O) ppm; MS (m/z, %): 474 (M ,
1
3
9); Anal. Calcd for C H N O : C, 70.88; H, 3.82; N,
28 18 4 4
CDCl ): δ 34.1 (CH), 84.2, 117.5, 122.7, 124.5, 125.2,
11.81%. Found: C, 71.05; H, 3.56; N, 11.98%.
3
1
1
1
26.1, 127.3, 128.5, 129.0, 129.7, 130.0, 130.3, 130.5,
33.5, 136.2, 141.7, 142.5, 146.4, 147.1, 148.2, 150.9,
3.2.9
| 16-(3,4-Dimethoxyphenyl)-4,16-dihydro-1H-benzo[a]
0
0
pyrimido[5 ,4 :5,6]pyrano[2,3-c]phenazine-1,3(2H)-dione (6i)
57.2 and 157.9 (Colefinic and C
), 160.2, 164.3 (2C=O)
arom
+
ꢀ
ppm; MS (m/z, %): 523 (M , 3); Anal. Calcd for
Red powder; yield 0.383 g (76%), mp 223–224 C; IR
C H ClN O : C, 61.90; H, 2.69; N, 13.37%. Found: C,
(KBr): νmax = 3195, 3040, 2915, 1728, 1680, 1584, 1531,
1487, 1415, 1379, 1340, 1263, 1139, 1002, 751 cm ; H
2
7
14
5 5
−1 1
62.12; H, 2.85; N, 13.62%.