1
110
N. A. ALSAIF ET AL.
0
0
1
2
24.10, 123.22, 118.67 (2C), 118.59, 118.07, 48.73, 38.87, 32.95 (2C), 4.1.3.11. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3 ,4 -c]uinoxaline-3-ylth-
þ
5.76, 25.45 (2C); MS (m/z): 501 (M þ 1, 100%); Anal. Calcd. for io)acetamido)-N-(4-fluorophenyl)benzamide (23k). White powder
ꢁ
ꢀ1
C H N O S (500.58): C, 59.99; H, 4.83; N, 22.39. Found: C, 59.85; (yield, 80%); m.p. ¼ 250–252 C. FT-IR (ꢀmax, cm ): 3289, 3108
2
5 24 8 2
1
H, 4.76; N, 22.11%.
(NH), 1645 (C¼O), 1604 (C¼N); H NMR (700 MHz, DMSO-d ) d
6
1
8
1
0.77 (s, 1H), 10.21 (s, 1H), 10.02 (s, 1H), 8.79 ꢀ 8.57 (m, 1H),
.55 ꢀ 8.41 (m, 1H), 7.96 (t, J ¼ 9.5 Hz, 2H), 7.78 (dt, J ¼ 35.0,
4
.1.3.7. N-(4-Acetylphenyl)-4-(2-(bis([1, 2, 4]triazolo)[4,3-a:3’,4’-
1
3
2.1 Hz, 5H), 7.26 ꢀ 7.14 (m, 3H), 4.59 (s, 2H); C NMR (176 MHz,
c]quinoxalin-3-ylthio)acetamido)benzamide (23g). Pale white crys-
ꢁ
ꢀ1
DMSO-d ) d 166.04, 165.20, 147.72, 142.11, 139.34, 138.78, 129.17
6
tal (yield, 80%); m.p. ¼ 275–277 C. FT-IR (ꢀmax, cm ): 3300 (NH),
1
(2C), 128.36 (2C), 124.08, 123.19, 122.61 (2C), 122.57 (2C), 118.84
2C), 118.58, 118.06, 115.68 (2C), 115.55 (2C), 38.90; MS (m/z): 513
1
1
1
1
655 (C¼O), 1593 (C¼N); H NMR (700 MHz, DMSO-d
6
) d 10.77 (s,
(
(
(
H), 10.14 (s, 1H), 7.97 (d, J ¼ 8.6 Hz, 2H), 7.81 (dd, J ¼ 8.0, 1.5 Hz,
H), 7.78 ꢀ 7.76 (m, 2H), 7.72 (d, J ¼ 8.7 Hz, 2H), 7.59 ꢀ 7.57 (m,
H), 7.54 (dd, J ¼ 8.5, 1.3 Hz, 1H), 7.40 ꢀ 7.37 (m, 1H), 7.36 ꢀ 7.34
þ
M
þ 1, 25%), 372 (100%); Anal. Calcd. For C25
8 2
H17FN O S
512.52): C, 58.59; H, 3.34; N, 21.86. Found: C, 58.34; H, 3.22;
1
3
N, 21.69%.
(m, 2H), 7.10 (t, J ¼ 7.4 Hz, 1H), 5.19 (s, 2H), 2.49 (s, 3H); C NMR
(
176 MHz, DMSO-d
39.71, 133.48, 132.47 (2C), 130.20 (2C), 130.04, 129.29, 129.23
2C), 129.05 (2C), 123.99, 123.94 (2C), 120.80 (2C), 118.83 (2C), io)acetamido)-N-(2-hydroxyphenyl)benzamide (23l). Off white crys-
6
) d 165.80, 165.23, 157.97, 154.85, 142.00,
0 0
.1.3.12. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3 ,4 -c]uinoxaline-3-ylth-
4
1
(
1
þ
ꢁ
ꢀ1
15.21, 45.80, 21.59; MS (m/z): 537 (M þ 1, 40%), 354 (40%); tal (yield, 71%); m.p. ¼ 282–284 C. FT-IR (ꢀmax, cm ): 3263 (NH),
1
Anal. Calcd. for C27
Found: C, 60.10; H, 3.66; N, 20.59%.
20
H N
O
8 3
S (536.57): C, 60.44; H, 3.76; N, 20.88. 1646 (C¼O), 1600 (C¼N); H NMR (700 MHz, DMSO-d
) d 10.78 (s,
6
1H), 10.02 (s, 1H), 9.76 (s, 1H), 9.46 (s, 1H), 8.60 (dd, J ¼ 8.1, 1.4 Hz,
1
H), 8.46 (dd, J ¼ 8.0, 1.7 Hz, 1H), 7.97 ꢀ 7.96 (m, 2H), 7.75 ꢀ 7.73
(
6
m, 3H), 7.69 (dt, J ¼ 8.1, 2.1 Hz, 2H), 7.04 ꢀ 7.03 (m, 1H),
4
.1.3.8. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3’,4’-c]quinoxalin-3-ylth-
1
3
.93 ꢀ 6.92 (m, 1H), 6.84 ꢀ 6.83 (m, 1H), 4.60 (s, 2H); C NMR
) d 166.05, 165.10, 149.68, 147.72, 142.24,
142.10, 139.33, 138.77, 129.49, 129.08 (2C), 128.36, 128.34, 126.46,
io)acetamido)-N-(3-chlorophenyl)benzamide (23h). Yellowish white
ꢁ
ꢀ1
(176 MHz, DMSO-d
6
crystal (yield, 63%); m.p. ¼ 280–282 C. FT-IR (ꢀmax, cm ): 3267,
1
3
109 (NH), 1701, 1647 (C¼O), 1593 (C¼N); H NMR (700 MHz,
1
1
26.03, 124.43, 124.06, 123.17, 119.53 (2C), 118.95, 118.57, 118.06,
DMSO-d ) d 10.79 (s, 1H), 10.30 (s, 1H), 10.02 (s, 1H), 8.61 (dd,
6
þ
16.50, 38.93; MS (m/z): 511 (M þ 1, 70%), 293 (100%); Anal.
J ¼ 8.1, 1.5 Hz, 1H), 8.47 (dd, J ¼ 7.9, 1.7 Hz, 1H), 7.98 ꢀ 7.95 (m,
Calcd. For C H N O S (510.53): C, 58.82; H, 3.55; N, 21.95. Found:
2
5 18 8 3
3
H), 7.78 ꢀ 7.73 (m, 4H), 7.70 (ddd, J ¼ 8.3, 2.1, 1.0 Hz, 1H), 7.38 (t,
13
C, 58.78; H, 3.50; N, 21.88%.
J ¼ 8.1 Hz, 1H), 7.15 (ddd, J ¼ 8.0, 2.1, 0.9 Hz, 1H), 4.59 (s, 2H);
C
NMR (176 MHz, DMSO-d ) d 166.08, 165.52, 147.71, 142.38, 142.12,
6
0
0
4
.1.3.13. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3 ,4 -c]uinoxaline-3-ylth-
141.23, 139.34, 138.78, 133.38, 130.76, 129.63, 129.30 (2C), 128.37,
124.08, 123.65, 123.20, 120.10 (2C), 119.03, 118.86 (2C), 118.59,
118.06, 38.89; Anal. Calcd. for C H ClN O S (528.98): C, 56.77; H,
3
io)acetamido)-N-(4-hydroxyphenyl)benzamide (23m). Pale yellow
ꢁ
ꢀ1
crystal (yield, 75%); m.p. ¼ 285–287 C. FT-IR (ꢀmax, cm ): 3414
2
5
17
8 2
1
(
NH), 1601 (C¼N); H NMR (700 MHz, DMSO-d
6
) d 10.75 (s, 1H),
.24; N, 21.18. Found: C, 56.37; H, 3.11; N, 20.99%.
1
8
6
0.01 (s, 1H), 9.93 (s, 1H), 9.26 (s, 1H), 8.63 ꢀ 8.54 (m, 1H),
.51 ꢀ 8.39 (m, 1H), 7.93 (d, J ¼ 8.7 Hz, 2H), 7.72 (dq, J ¼ 14.7, 7.1,
.6 Hz, 4H), 7.55 ꢀ 7.49 (m, 2H), 6.79 ꢀ 6.70 (m, 2H), 4.59 (s, 2H);
4
.1.3.9. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3’,4’-c]quinoxalin-3-ylth-
io)acetamido)-N-(4-chlorophenyl)benzamide (23i). Yellow crystal
13
6
C NMR (176 MHz, DMSO-d ) d 165.99, 164.72, 154.09 (2C),
ꢁ
ꢀ1
(
(
yield, 65%); m.p. ¼ 277–279 C. FT-IR (ꢀmax, cm ): 3382, 3111
1
(
(
47.74, 142.05, 139.30, 138.77, 131.21, 130.33, 128.98 (2C), 128.33
2C), 124.01, 123.12, 122.74 (2C), 118.81(2C), 118.55, 118.02, 115.42
1
NH), 1674 (C¼O), 1595 (C¼N); H NMR (700 MHz, DMSO-d ) d
6
1
8
7
2
1
0.78 (s, 1H), 10.28 (s, 1H), 10.03 (s, 1H), 8.62 (d, J ¼ 8.0 Hz, 1H),
.53 ꢀ 8.44 (m, 1H), 7.96 (d, J ¼ 8.5 Hz, 3H), 7.82 (d, J ¼ 8.5 Hz, 2H),
.78 (d, J ¼ 9.1 Hz, 1H), 7.74 (d, J ¼ 8.4 Hz, 2H), 7.41 (d, J ¼ 8.6 Hz,
þ
2C), 38.92; MS (m/z): 511(M þ 1, 30%); Anal. Calcd. For
25 18 8 3
C H N O S (510.53): C, 58.82; H, 3.55; N, 21.95. Found: C, 58.63;
H, 3.48; N, 21.73%.
1
3
H), 4.59 (s, 2H); C NMR (176 MHz, DMSO-d ) d 166.07, 165.39,
6
47.71, 142.29, 142.15, 139.37, 138.79, 138.72, 129.80, 129.26
0
0
4
.1.3.14. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3 ,4 -c]uinoxaline-3-ylth-
(
2C), 128.98 (2C), 128.38 (2C), 127.57, 124.12, 123.24, 122.27 (2C),
18.86 (2C), 118.61, 118.08, 38.88; Anal. Calcd. for C25 17ClN
528.98): C, 56.77; H, 3.24; N, 21.18. Found: C, 56.44; H, 3.19;
N, 20.85%.
io)acetamido)-N-(2-hydroxy-4-nitrophenyl)benzamide (23n). Red
1
(
H
8 2
O S
ꢁ
ꢀ1
crystal (yield, 68%); m.p. ¼ 265–267 C. FT-IR (ꢀmax, cm ): 3294,
1
3
101 (NH), 2927 (CH aliphatic), 1653 (C¼O), 1603 (C¼N); H NMR
(
700 MHz, DMSO-d ) d 11.14 (s, 1H), 10.82 (s, 1H), 10.02 (s, 1H),
6
9
1
2
.49 (s, 1H), 8.61 (dd, J ¼ 8.1, 1.5 Hz, 1H), 8.47 (dd, J ¼ 7.8, 1.8 Hz,
0
0
4
.1.3.10. 4-(2-(Bis([1, 2, 4]triazolo)[4,3-a:3 ,4 -c]uinoxaline-3-ylth-
H), 8.25 (d, J ¼ 8.9 Hz, 1H), 7.98 ꢀ 7.96 (m, 2H), 7.79 (dd, J ¼ 8.9,
io)acetamido)-N-(2,5-dichlorophenyl)benzamide (23j). White crystal
.6 Hz, 1H), 7.78 ꢀ 7.75 (m, 3H), 7.74 (dd, J ¼ 6.7, 2.1 Hz, 2H), 4.60
ꢁ
ꢀ1
(
yield, 78%); m.p. ¼ 260–262 C. FT-IR (ꢀmax, cm ): 3429 (NH),
13
(s, 2H); C NMR (176 MHz, DMSO-d ) d 166.14, 165.06, 148.55,
6
1
1
1
1
672 (C¼O), 1511 (C¼N); H NMR (700 MHz, DMSO-d ) d 10.80 (s,
6
1
1
1
47.70, 143.66, 142.72, 142.13, 139.35, 138.78, 133.63, 129.27 (2C),
28.90, 128.38, 128.36, 124.08, 123.20, 121.83, 119.05 (2C), 118.59,
18.07, 115.57, 109.89, 38.91; MS (m/z): 554 (M ꢀ 1, 70%); Anal.
H), 10.03 (s, 2H), 8.62 (dd, J ¼ 8.0, 1.5 Hz, 1H), 8.48 (dd, J ¼ 7.9,
.7 Hz, 1H), 7.99 ꢀ 7.97 (m, 2H), 7.77 (dt, J ¼ 5.0, 2.2 Hz, 2H), 7.76
þ
(
m, 2H), 7.75 (s, 1H), 7.61 (d, J ¼ 8.6 Hz, 1H), 7.38 (dd, J ¼ 8.6,
Calcd. For C H N O S (555.53): C, 54.05; H, 3.08; N, 22.69. Found:
2
5 17 9 5
13
2
1
1
1
.6 Hz, 1H), 4.60 (s, 2H); C NMR (176 MHz, DMSO-d ) d 166.11,
6
C, 53.85; H, 2.97; N, 22.43%.
65.23, 147.70, 142.59, 142.15, 139.37, 138.79, 136.95, 131.89,
31.35, 129.39 (2C), 128.76, 128.39, 128.37, 128.20, 127.90, 127.39,
24.11, 123.23, 118.94 (2C), 118.60, 118.08, 38.89; MS (m/z): 563 4.1.4. General procedure for the synthesis of compounds 24a–c
þ
0 0
M , 30%), 420 (65%); Anal. Calcd. For C H Cl N O S (563.42): C, A mixture of potassium salt of bis([1, 2, 4]triazolo)[4,3-a:3 ,4 -c]qui-
25 16 2 8 2
(
5
3.30; H, 2.86; N, 19.89. Found: C, 53.01; H, 2.77; N, 19.66%.
noxaline-3-thiol 14 (0.5 g, 0.001 mol) and 2-chloro-N-(4–(2-