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EISSA ET AL.
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J = 8.4 Hz, H‐3 of pyridine, 7.55–7.89 (m, 10H, Ar‐H), 8.32 (s, 1H, Ar‐
H, N–CH═N), 10.04 (s, 1H, exchangeable with D2O, –CONH), and
10.65 (s, 1H, exchangeable with D2O, –SO2NH); 13C NMR (DMSO‐d6,
100 MHz) δ (ppm): 34.92, 114.31, 116.98, 117.90, 118.87(2), 126.27,
128.29, 128.30(3), 128.23, 135.57, 138.21, 139.09, 140.79, 143.31,
143.36, 150.44, 151.62, 153.59, and 167.59; Anal. calcd. for
C22H17N7O3S2 (491.54): C, 53.76; H, 3.49; N, 19.95. Found: C,
53.99%; H, 3.88%; N, 20.35%.
(C═O), 1,597 (C═N), and 1,136 (SO2); 1H NMR (DMSO‐d6) δ (ppm): 4.24
(s, 2H, SCH2), 4.40 (s, 2H, –NHCH2), 7.30 (br, s, 2H, exchangeable with
D2O, –NH2), 7.43 (d, 2H, Ar‐H, J = 7.88 Hz, H‐3, and H‐5 of phenyl),
7.62 (dd, 1H, J = 7.5, 8.1 Hz, Ar‐H, H‐8 of quinoxaline), 7.68 (dd, 1H, J =
7.5, 8.0 Hz, Ar‐H, H‐7 of quinoxaline), 7.70 (d, 2H, Ar‐H, J = 7.88 Hz, H‐2,
and H‐6 of phenyl), 7.86 (d, 1H, J = 8.1 Hz, Ar‐H, H‐9 of quinoxaline),
8.34 (d, 1H, J = 8.0 Hz, Ar‐H, H‐6 of quinoxaline), 8.90 (s, 1H, Ar‐H,
N–CH═N), and 10.09 (s, 1H, exchangeable with D2O, –NH); 13C NMR
(DMSO‐d6, 100 MHz) δ (ppm): 32.93, 42.75, 117.04, 123.97, 126.07
(2C), 127.83 (2C), 128.26, 128.44, 128.71, 135.56, 138.21, 141.90,
143.05, 143.79, 151.66, and 167.56; DEPT (DMSO‐d6, 100 MHz) δ
(ppm): 32.93, 42.75, 117.03, 126.06 (2C), 127.82 (2C), 128.25, 128.44,
128.70, and 138.21; Anal. calcd. for C18H16N6O3S2 (428.49): C, 50.46;
H, 3.76; N, 19.61. Found: C, 50.78%; H, 3.44%; N, 19.85%.
2‐([1,2,4]Triazolo[4,3‐a]quinoxalin‐4‐ylthio)‐N‐(4‐(N‐(thiazol‐2‐yl)‐
sulfamoyl)phenyl)acetamide (19c)
Yellowish white crystals (yield, 70%); m.p. = 232–235°C. IR (KBr, cm−1):
3,267, 3,185 (2NH), 3,108 (CH aromatic), 2,915 (CH aliphatic), 1,691
(C═O), 1,590 (C═N), and 1,138 (SO2); 1H NMR (DMSO‐d6) δ (ppm): 4.41
(s, 2H, –SCH2), 6.77 (d, 1H, J = 4.8 Hz, H‐5 of thiazol), 7.19 (d, 1H, J = 4.8
Hz, H‐4 of thiazol), 7.54–7.58 (m, 3H, Ar‐H, H‐7, H‐8 and H‐9 of
quinoxaline), 7.67 (d, 2H, J = 8.2 Hz, Ar‐H, H‐3 and H‐5 of phenyl), 7.73
(d, 2H, J = 8.2 Hz , Ar‐H, H‐2 and H‐6 of phenyl), 7.79 (d, 1H, J = 8 Hz,
Ar‐H, H‐6 of quinoxaline), 8.24 (s, 1H, Ar‐H, N–CH═N), 10.00 (s, 1H,
exchangeable with D2O, CONH), and 10.68 (s, 1H, exchangeable with
D2O, –SO2NH): 13C NMR (DMSO‐d6, 100 MHz) δ (ppm): 34.45, 108.48,
116.93, 119.29(2), 123.92, 124.98, 127.46(2), 128.20, 128.29, 128.60,
135.53, 137.41, 138.08, 141.84, 142.49, 151.51, 166.89, and 168.19;
DEPT (DMSO‐d6, 100 MHz) δ (ppm): 34.45, 108.47, 116.92, 119.38(2),
124.99, 127.47(2), 128.20, 128.29, 128.60, 138.08; MS (m/z): 497 (M+,
14.69%), 204.03 (45.39%), 155.23 (45.18%), and 78.64 (100% base
beak); Anal. calcd. for C20H15N7O3S3 (497.57): C, 48.28; H, 3.04; N,
19.71. Found: C, 48.58%; H, 3.44%; N, 20.05%.
2‐([1,2,4]Triazolo[4,3‐a]quinoxalin‐4‐ylthio)acetamide (22
)
Beige yellow crystals (yield, 70%); m.p. = 255–256°C. IR (KBr, cm−1):
3,197, 3,120 (NH2), 3,066 (CH aromatic), 2,925 (CH aliphatic), 1,667
(C═O), and 1,624 (C═N); 1H NMR (DMSO‐d6) δ (ppm): 4.13 (s, 2H,
CH2), 7.27 (s, 2H, exchangeable with D2O, –NH2), 7.64 (dd, 1H, J =
7.5, 8.1 Hz, Ar‐H, H‐8 of quinoxaline), 7.71 (dd, 1H, J = 7.5, 8.1 Hz, Ar‐
H, H‐7 of quinoxaline), 7.92 (d, 1H, J = 8.1 Hz, Ar‐H, H‐9 of
quinoxaline), 8.34 (d, 1H, J = 7.5 Hz, Ar‐H, H‐6 of quinoxaline), and
10.10 (s, 1H, Ar‐H, N–CH═N); 13C NMR (DMSO‐d6, 100 MHz) δ
(ppm): 33.01, 117.07, 124.00, 128.30, 128.49, 128.66, 135.63,
138.21, 141.93, 151.78, and 169.22; DEPT (DMSO‐d6, 100 MHz) δ
(ppm): 33.01 (1CH2), 117.07, 128.30, 128.49, 128.66, and 138.22
(5CH); MS (m/z): 259 (M+, 24.08%), 212 (48.79%), 202.60 (14.16%),
and 96.75 (100% base beak); Anal. calcd. for C11H9N5OS (259.29): C,
50.96; H, 3.50; N, 27.01. Found: C, 50.61%; H, 3.11%; N, 27.42%.
3‐([1,2,4]Triazolo[4,3‐a]quinoxalin‐4‐ylthio)‐N‐(4‐sulfamoylphenyl)‐
propanamide (20)
Brown crystals (yield, 67%); m.p. = 264–265°C. IR (KBr, cm−1): 3,240,
3,183 (NH, NH2), 3,052 (CH aromatic), 2,925 (CH aliphatic), 1,680
(C═O), 1,592 (C═N), and 1,155 (SO2); 1H NMR (DMSO‐d6) δ ppm:
2.99 (t, 2H, J = 6.5 Hz, COCH2), 3.67 (t, 2H, J = 6.5 Hz, –SCH2). 7.25
(s, 2H, exchangeable with D2O, –NH2), 7.58 (dd, 1H, J = 7.6, 8.4 Hz,
Ar‐H, H‐8 of quinoxaline), 7.63 (dd, 1H, J = 7.6, 8.0 Hz, Ar‐H, H‐7 of
quinoxaline), 7.70 (d, 1H, J = 8.4 Hz, Ar‐H, H‐9 of quinoxaline), 7.75
(d, 1H, J = 8.0 Hz, Ar‐H, H‐6 of quinoxaline), 7.79 (d, 2H, J = 8.0 Hz,
Ar‐H, H‐2, and H‐6 of phenyl), 7.91 (d, 2H, J = 8.0 Hz, Ar‐H, H‐3, and
H‐5 of phenyl), 8.30 (s, 1H, Ar‐H, N–CH═N), and 10.05 (s, 1H,
exchangeable with D2O, –NH); 13C NMR (DMSO‐d6, 100 MHz) δ
(ppm): 24.21, 36.08, 116.93, 119.07(2), 123.85, 127.17(3), 128.16,
128.50, 135.66, 138.14, 138.76, 142.01, 142.35, 151.95, and 170.38;
DEPT (DMSO‐d6, 100 MHz) δ (ppm): 24.21, 36.09 (2CH2), 116.92,
119.06(2), 127.17(3), 128.16, and 128.49(2); Anal. calcd. for
C18H16N6O3S2 (428.49): C, 50.46; H, 3.76; N, 19.61. Found: C,
50.11%; H, 3.31%; N, 19.02%.
2‐([1,2,4]Triazolo[4,3‐a]quinoxalin‐4‐ylthio)‐N‐(4‐acetylphenyl)acet-
amide (23)
Brown powder (yield, 75%); m.p. = 117–118°C. IR (KBr, cm−1): 3,248
(NH), 3,045 (CH aromatic), 2,900 (CH aliphatic), 1,675 (C═O), and
1,594 (C═N); 1H NMR (DMSO‐d6) δ (ppm): 2.66 (s, 3H, –COCH3),
4.45 (s, 2H, CH2), 7.55 (dd, 1H, J = 7.4, 8.0 Hz, Ar‐H, H‐8 of
quinoxaline), 7.62 (dd, 1H, J = 7.4, 8.6 Hz, Ar‐H, H‐7 of quinoxaline),
7.79 (d, 1H, J = 8.0 Hz, Ar‐H, H‐9 of quinoxaline), 7.82 (d, 1H, J = 8.6
Hz, Ar‐H, H‐6 of quinoxaline), 7.99 (d, 2H, J = 7.5 Hz, Ar‐H, H‐2, and
H‐6 of phenyl), 8.35 (d, 2H, J = 7.5 Hz, Ar‐H, H‐3, and H‐5 of phenyl),
10.10 (s, 1H, Ar‐H, N–CH═N), and 10.80 (s, 1H, exchangeable with
D2O, –NH); 13C NMR (DMSO‐d6, 100 MHz) δ (ppm): 27.60, 34.52,
116.16, 118.88, 119.05(2), 123.34, 126.21, 128.26, 129.62(2),
135.56, 138.22, 143.42, 146.72, 151.57, 166.90, 170.25, and
196.88; Anal. calcd. for C19H15N5O2S (377.42): C, 60.47; H, 4.01;
N, 18.56. Found: C, 60.22%; H, 4.41%; N, 18.92%.
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4.1.5
General procedure for the synthesis of
2‐([1,2,4]Triazolo[4,3‐a]quinoxalin‐4‐ylthio)‐N‐(4‐sulfamoylbenzyl)‐
compounds 24a–g
acetamide (21
)
Yellow crystals (yield, 60%); m.p. = 215–217°C. IR (KBr, cm−1): 3,310,
A mixture of the potassium salt 17 (2.94 g, 0.01 mol) and the
3,180 (NH, NH2), 3,079 (CH aromatic), 2,925 (CH aliphatic), 1,685
different alkyl halids (0.025 mol), namely, methyl bromide, ethyl