MOHEBAT ET AL.
5
ethanol to give the pure product 6. The spectral and analyti-
CDCl ): δ 21.2 (CH ), 65.7 (CH), 115.5, 122.0, 122.2,
3
3
cal data are presented below:
122.9, 124.5, 125.6, 127.5, 128.5, 128.7, 128.8, 129.1,
1
1
29.5, 129.7, 130.1, 130.4, 131.0, 132.3, 134.6, 137.2,
3
.2.1
| 1-(4-Chlorophenyl)-3-tosyl-2,3-dihydro-1H-benzo[a]
38.5, 140.7, 141.8, 142.5, 146.3, 147.1 and 148.8 (C
olefinic
pyrazolo[3,4-c]phenazine (6a)
+
and Carom) ppm; MS (m/z, %): 581 (M , 7); Anal. Calcd for
C H BrN O S: C, 61.97; H, 3.64; N, 9.64; S, 5.51%.
ꢀ
Brown powder; yield 0.467 g (87%), mp 261–263 C; IR
30
21
4 2
(
1
KBr): νmax = 3285, 3115, 2920, 1636, 1585, 1535, 1465,
403, 1337, 1315, 1282, 1161, 1024, 757 cm ; H NMR
Found: C, 62.23; H, 3.51; N, 9.85; S, 5.82%.
−1 1
(
6
7
400 MHz, CDCl ): δ 2.20 (s, 3H, CH ), 5.29 (s, 1H, CH),
.93 (d, 1H, J = 8.4 Hz, Ar-H), 7.03–7.58 (m, 5H, Ar-H),
.62 (d, 2H, J = 8.8 Hz, Ar-H), 7.76 (d, 2H, J = 8.0 Hz,
3.2.4
| 1-(3-Nitrophenyl)-3-tosyl-2,3-dihydro-1H-benzo[a]
3
3
pyrazolo[3,4-c]phenazine (6d)
ꢀ
Brown powder; yield 0.454 g (83%), mp 281–283 C; IR
(KBr): νmax = 3230, 3045, 2900, 1634, 1586, 1516, 1452,
1403, 1373, 1333, 1282, 1161, 1046, 753 cm ; H NMR
Ar-H), 7.86 (d, 2H, J = 8.0 Hz, Ar-H), 7.88–8.18 (m, 2H,
Ar-H), 8.24 (d, 1H, J = 8.0 Hz, Ar-H), 8.33–8.47 (m, 1H,
Ar-H), 8.54 (d, 1H, J = 8.0 Hz, Ar-H), 9.22 (d, 1H,
−
1 1
(400 MHz, CDCl ): δ 2.20 (s, 3H, CH ), 5.31 (s, 1H, CH),
3
3
1
3
J = 7.6 Hz, Ar-H), 9.97 (s, 1H, NH) ppm; C NMR
7.23 (d, 1H, J = 8.0 Hz, Ar-H), 7.30 (d, 1H, J = 8.4 Hz,
Ar-H), 7.33–7.37 (m, 1H, Ar-H), 7.41 (d, 2H, J = 8.0 Hz,
Ar-H), 7.46 (d, 1H, J = 8.4 Hz, Ar-H), 7.56 (d, 1H,
J = 8.8 Hz, Ar-H), 7.64 (d, 1H, J = 8.0 Hz, Ar-H),
7.68–8.08 (m, 2H, Ar-H), 8.10 (d, 2H, J = 8.4 Hz, Ar-H),
8.12–8.18 (m, 1H, Ar-H), 8.36 (d, 1H, J = 8.4 Hz, Ar-H),
8.72 (s, 1H, Ar-H), 9.28–9.42 (m, 1H, Ar-H), 10.11 (s, 1H,
(75 MHz, CDCl ): δ 21.2 (CH ), 64.8 (CH), 116.2, 120.7,
3 3
1
1
1
23.8, 124.1, 125.7, 127.5, 128.3, 128.4, 129.1, 129.4,
29.9, 130.0, 130.2, 130.9, 131.1, 131.6, 132.2, 137.5,
38.4, 140.5, 141.6, 142.1, 146.0, 146.8 and 148.5 (C
olefinic
+
and Carom) ppm; MS (m/z, %): 537 (M , 4); Anal. Calcd for
C H ClN O S: C, 67.09; H, 3.94; N, 10.43; S, 5.97%.
Found: C, 67.34; H, 4.12; N, 10.72; S, 6.15%.
3
0
21
4 2
13
NH) ppm; C NMR (75 MHz, CDCl ): δ 21.8 (CH ), 65.7
3 3
(
1
1
CH), 116.5, 121.6, 122.7, 124.3, 126.1, 127.5, 128.6,
29.1, 129.4, 129.9, 130.1, 130.4, 130.6, 131.5, 132.7,
35.8, 137.2, 138.1, 142.0, 142.6, 144.1, 146.3, 147.2,
3
.2.2
| 1-(4-Nitrophenyl)-3-tosyl-2,3-dihydro-1H-benzo[a]
pyrazolo[3,4-c]phenazine (6b)
ꢀ
Brown powder; yield 0.465 g (85%), mp 288–290 C; IR
148.2 and 148.8 (C
547 (M , 3); Anal. Calcd for C H N O S: C, 65.80; H,
30 21 5 4
3.87; N, 12.79; S, 5.86%. Found: C, 66.03; H, 4.11; N,
12.62; S, 6.04%.
and Carom) ppm; MS (m/z, %):
olefinic
+
(KBr): νmax = 3310, 3060, 2915, 1644, 1592, 1515, 1469,
−1 1
1
406, 1383, 1340, 1282, 1166, 1048, 756 cm ; H NMR
(400 MHz, CDCl ): δ 2.27 (s, 3H, CH ), 5.37 (s, 1H, CH),
3 3
7.20 (d, 1H, J = 8.0 Hz, Ar-H), 7.56 (d, 2H, J = 7.6 Hz,
Ar-H), 7.59 (d, 2H, J = 8.8 Hz, Ar-H), 7.68 (d, 1H,
J = 8.4 Hz, Ar-H), 7.72 (d, 2H, J = 8.0 Hz, Ar-H),
3.2.5
| 1-(2-Nitrophenyl)-3-tosyl-2,3-dihydro-1H-benzo[a]
pyrazolo[3,4-c]phenazine (6e)
ꢀ
7
8
1
.76–8.30 (m, 3H, Ar-H), 8.33 (d, 2H, J = 8.8 Hz, Ar-H),
Brown powder; yield 0.438 g (80%), mp 219–221 C; IR
(KBr): νmax = 3265, 3030, 2885, 1635, 1589, 1525, 1490,
1468, 1399, 1337, 1281, 1146, 1050, 757 cm ; H NMR
.42–8.65 (m, 2H, Ar-H), 9.28 (d, 1H, J = 8.0 Hz, Ar-H),
1
3
−1 1
0.02 (s, 1H, NH) ppm; C NMR (75 MHz, CDCl ): δ 21.3
3
(
CH ), 65.2 (CH), 115.7, 121.5, 122.3, 124.5, 125.2, 127.3,
(400 MHz, CDCl ): δ 2.20 (s, 3H, CH ), 5.31 (s, 1H, CH),
3
3
3
1
1
1
28.5, 128.8, 129.0, 129.5, 129.7, 130.1, 130.2, 130.5,
31.3, 131.6, 132.5, 136.8, 138.3, 141.9, 142.8, 145.2,
6.91 (d, 1H, J = 8.0 Hz, Ar-H), 7.13 (d, 1H, J = 8.0 Hz,
Ar-H), 7.17–7.37 (m, 2H, Ar-H), 7.40 (d, 1H, J = 8.4 Hz,
Ar-H), 7.45–7.75 (m, 3H, Ar-H), 7.79 (d, 2H, J = 8.4 Hz,
Ar-H), 7.83–7.92 (m, 1H, Ar-H), 7.94 (d, 1H, J = 8.0 Hz,
Ar-H), 7.98–8.66 (m, 1H, Ar-H), 9.14 (d, 1H, J = 7.6 Hz,
46.3, 147.4 and 150.1 (C
and Carom) ppm; MS (m/z,
olefinic
+
%
): 547 (M , 1); Anal. Calcd for C H N O S: C,
30 21 5 4
6
4
5.80; H, 3.87; N, 12.79; S, 5.86%. Found: C, 65.62; H,
.07; N, 12.87; S, 5.98%.
13
Ar-H), 10.13 (s, 1H, NH) ppm; C NMR (75 MHz,
CDCl ): δ 21.3 (CH ), 62.6 (CH), 115.6, 121.2, 123.8,
3
3
3
.2.3
| 1-(4-Bromophenyl)-3-tosyl-2,3-dihydro-1H-benzo[a]
1
1
24.2, 125.91, 128.1, 128.5, 129.0, 129.4, 129.6, 130.3,
30.7, 131.0, 131.3, 132.5, 135.5, 137.5, 138.8, 140.7,
pyrazolo[3,4-c]phenazine (6c)
ꢀ
Brown powder; yield 0.470 g (81%), mp 250–252 C; IR
142.1, 142.8, 146.2, 146.7, 147.2 and 152.1 (C
Carom) ppm; MS (m/z, %): 547 (M , 8); Anal. Calcd for
and
olefinic
+
(KBr): νmax = 3280, 3025, 2895, 1635, 1586, 1523, 1468,
−1 1
1
397, 1377, 1337, 1279, 1164, 1048, 757 cm ; H NMR
C H N O S: C, 65.80; H, 3.87; N, 12.79; S, 5.86%.
30 21 5 4
(
400 MHz, CDCl ): δ 2.24 (s, 3H, CH ), 5.32 (s, 1H, CH),
Found: C, 65.98; H, 3.97; N, 12.95; S, 6.12%.
3
3
7
7
7
7
.19 (d, 2H, J = 8.4 Hz, Ar-H), 7.28–7.34 (m, 1H, Ar-H),
.36 (d, 1H, J = 8.0 Hz, Ar-H), 7.54–7.57 (m, 1H, Ar-H),
.59 (d, 2H, J = 8.4 Hz, Ar-H), 7.67–7.72 (m, 1H, Ar-H),
.78 (d, 2H, J = 8.0 Hz, Ar-H), 7.83 (d, 2H, J = 8.4 Hz,
3.2.6
| 1-Phenyl-3-tosyl-2,3-dihydro-1H-benzo[a]pyrazolo
[
3,4-c]phenazine (6f)
ꢀ
Brown powder; yield 0.412 g (82%), mp 249–250 C; IR
(KBr): νmax = 3290, 3020, 2845, 1628, 1580, 1519, 1458,
1399, 1333, 1283, 1140, 1023, 754 cm ; H NMR
Ar-H), 7.84–8.63 (m, 3H, Ar-H), 9.29 (d, 1H, J = 8.0 Hz,
Ar-H), 10.14 (s, 1H, NH) ppm; C NMR (75 MHz,
1
3
−1
1