H. Bera et al. / European Journal of Medicinal Chemistry 67 (2013) 325e334
331
OMe), 7.11 (dd, 1H, H-40, J ¼ 8.1, 2.1 Hz), 7.45 (t, 1H, H-50, J ¼ 7.9 Hz),
4.1.17. 2-(4-Fluorophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-
a][1,3,5]triazin-7(4H)-one (5m)
7.54 (s,1H, H-20), 7.64 (d,1H, H-60, J ¼ 7.5 Hz),13.10 (s,1H, NH),14.32
(br. s, 1H, NH); 13C NMR (75 MHz, DMSO-d6):
d
55.1 (OMe), 111.2
The title compound was isolated as white pþowder (67%); mp
(C-20), 116.6 (C-40), 118.9 (C-60), 130.1 (C-50), 130.4 (C-10), 141.1 (C-30),
151.3 (C-2), 159.4 (C-9), 161.7 (C-7), 175.2 (C-5); Anal. calcd. for
262 ꢁC (EtOHewater); ESI-MS m/z 262.3 (M ꢀ 1) ; purity >95%; tR
2.13 min (B); 1H NMR (300 MHz, DMSO-d6): 7.37 (dd, 2H, H-30 and
d
C
11H9N5O2S: C, 47.99; H, 3.30; N, 25.44. Found: C, 47.23; H, 3.21; N,
H-50, J ¼ 8.9, 8.9 Hz), 8.09 (dd, 2H, H-20 and H-60, J ¼ 8.7, 5.7 Hz),13.12
25.16.
(s, 1H, NH), 14.20 (br. s, 1H, NH); 13C NMR (75 MHz, DMSO-d6):
d
116.0 (d, C-30 and C-50, J ¼ 21.8 Hz), 125.7 (d, C-10, J ¼ 2.9 Hz), 128.9
4.1.12. 3-(7-Oxo-5-thioxo-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]
[1,3,5]triazin-2-yl)benzonitrile (5h)
(d, C-20 and C-60, J ¼ 8.7 Hz),141.1 (C-2),151.4 (C-9),161.0 (C-7),163.5
(d, C-40, J ¼ 247.8 Hz), 175.2 (C-5); Anal. calcd. for C10H6FN5OS: C,
45.62; H, 2.30; N, 26.60. Found: C, 45.24; H, 2.14; N, 26.28.
The title compound was isolated as white crystallineþpowder
(67%); mp >300 ꢁC (acetic acid); ESI-MS m/z 287.0 (M ꢀ 1) ; purity
>95%; tR 4.07 min (B); 1H NMR (300 MHz, DMSO-d6):
d
7.48e8.57
4.1.18. 2-(4-Methylphenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo
[1,5-a][1,3,5]triazin-7(4H)-one (5n)
(m, 4H, AreH), 13.10 (s, 1H, NH), 14.38 (br. s, 1H, NH). 13C NMR
(75 MHz, DMSO-d6):
d
126.5 (C-30), 129.7 (CN), 129.8 (C-20), 130.0
The title compound was isolated as white powder (78%); mp
(C-50), 130.1 (C-10), 135.6 (C-60), 141.9 (C-40), 152.2 (C-2), 162.1 (C-9),
168.1 (C-7), 176.0 (C-5); Anal. calcd. for C11H6N6OS: C, 48.88; H,
2.24; N, 31.09. Found: C, 48.12; H, 2.11; N, 30.15.
296e297 ꢁC (EtOHewater); ESI-MS m/z 258.1 (M ꢀ 1)þ; purity
>95%; tR 2.19 min (B); 1H NMR (300 MHz, DMSO-d6):
d 2.38 (s, 3H,
ArMe), 7.34 (d, 2H, H-30 and H-50, J ¼ 7.9), 7.94 (d, 2H, H-20 and H-60,
J ¼ 7.9), 13.07 (s, 1H, NH), 14.26 (br. s, 1H, NH). 13C NMR (75 MHz,
4.1.13. 2-(4-Nitrophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo[1,5-
a][1,3,5]triazin-7(4H)-one (5i)
DMSO-d6): d
20.95 (Me), 126.38 (C-40), 126.46 (C20 and C-60), 129.45
(C-30 and C-50), 140.44 (C-10), 141.11 (C-2), 151.22 (C-9), 161.86 (C-7),
175.14 (C-5); Anal. calcd. for C11H9N5OS: C, 50.95; H, 3.50; N, 27.01.
Found: C, 50.15; H, 3.24; N, 27.26.
The title compound was isolated as off-white powder (65%);
mp >300 ꢁC (EtOHewater); ESI-MS m/z 289.1 (M ꢀ 1)þ; purity
>95%; tR 2.13 min (B); 1H NMR (300 MHz, DMSO-d6):
d 8.29 (d, 2H,
H-30 and H-50, J ¼ 8.7 Hz), 8.39 (d, 2H, H-20 and H-60, J ¼ 9.0 Hz),
4.1.19. 2-(4-Methoxyphenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo
[1,5-a][1,3,5]triazin-7(4H)-one (5o)
13.21 (s, 1H, NH), 14.28 (br. s, 1H, NH); 13C NMR (75 MHz, DMSO-
d6):
d
124.3 (C20 and C-60), 127.7 (C-30 and C-50), 135.0 (C-40), 141.1
The title compound was isolated as white crystalline powder
(C-10), 148.5 (C-2), 151.7 (C-9), 160.1 (C-7), 175.3 (C-5); Anal. calcd.
for C10H6N6O3S: C, 41.38; H, 2.08; N, 28.95. Found: C, 41.25; H,
2.05; N, 28.12.
(63%); mp 270e271 ꢁC (acetic acid); ESI-MS m/z 288.1 (M ꢀ 1)þ;
purity >95%; tR 2.15 min (B); 1H NMR (300 MHz, DMSO-d6):
d 3.84
(s, 3H, OMe), 7.08 (d, 2H, H-30 and H-50, J ¼ 8.7 Hz), 7.99 (d, 2H, H-20
and H-60, J ¼ 9.0 Hz), 13.07 (s, 1H, NH), 14.11 (br. s, 1H, NH); 13C NMR
4.1.14. 5-Thioxo-2-(4-(trifluoromethyl)phenyl)-5,6-dihydro-[1,2,4]
triazolo[1,5-a][1,3,5]triazin-7(4H)-one (5j)
(75 MHz, DMSO-d6): d
55.25 (MeO), 114.29 (C20 and C-60), 121.52 (C-
40), 128.17 (C-30 and C-50), 141.13 (C-10), 151.20 (C-2), 161.12 (C-9),
161.75 (C-7), 175.12 (C-5); Anal. calcd. for C11H9N5O2S: C, 47.99; H,
3.30; N, 25.44. Found: C, 47.56; H, 3.19; N, 25.02.
The title compound was isolated as white pþowder (69%); mp
280 ꢁC (EtOHewater); ESI-MS m/z 312.0 (M ꢀ 1) ; purity >95%; tR
2.15 min (B); 1H NMR (300 MHz, DMSO-d6): 7.91 (d, 2H, H-30 and
d
H-50, J ¼ 8.3), 8.26 (d, 2H, H-20 and H-60, J ¼ 8.3), 13.18 (s, 1H, NH),
4.1.20. 4-(7-Oxo-5-thioxo-4,5,6,7-tetrahydro-[1,2,4]triazolo[1,5-a]
[1,3,5]triazin-2-yl)benzonitrile (5p)
14.36 (br. s, 1H, NH); 13C NMR (75 MHz, DMSO-d6):
d 123.9 (q, CF3,
J ¼ 272.2 Hz), 125.9 (q, C-30 and C-50, J ¼ 3.4 Hz), 127.3 (C-20 and C-
60), 130.5 (q, C-40, J ¼ 32.0 Hz), 133.0 (C-10), 141.1 (C-2), 151.7 (C-9),
160.6 (C-7), 175.3 (C-5); Anal. calcd. for C11H6F3N5OS: C, 42.18; H,
1.93; N, 22.36. Found: C, 41.54; H, 1.82; N, 22.21.
The title compound was isolated as white powder (69%); mp
>300 ꢁC (EtOHewater); ESI-MS m/z 287.0 (M ꢀ 1)þ; purity >95%; tR
4.06 min (B); 1H NMR (300 MHz, DMSO-d6): 8.02 (d, 2H, H-30 and H-
d
50, J ¼ 8.4 Hz), 8.12 (d, 2H, H-20 and H-60, J ¼ 8.4 Hz),13.11 (s,1H, NH),
14.44 (br. s, 1H, NH); 13C NMR (75 MHz, DMSO-d6): 126.3 (C-30 and
d
4.1.15. 2-(4-Chlorophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo
[1,5-a][1,3,5]triazin-7(4H)-one (5k)
C-50), 128.1 (C-20 and C-60), 131.6 (CN), 136.0 (C-40), 141.2 (C-10), 151.7
(C-2),161.2 (C-9),167.2 (C-5),175.4 (C-7); Anal. calcd. for C11H6N6OS:
C, 48.88; H, 2.24; N, 31.09. Found: C, 48.52; H, 2.08; N, 30.58.
The title compound was isolated as white powder (66%); mp
281e282 ꢁC (EtOHewater); ESI-MS m/z 278.0 (M ꢀ 1)þ; purity
>95%; tR 2.18 min (B); 1H NMR (300 MHz, DMSO-d6):
d
7.61 (d, 2H,
4.1.21. 2-(3,4-Dichlorophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo
[1,5-a][1,3,5]triazin-7(4H)-one (5q)
H-30 and H-50, J ¼ 8.3), 8.05 (d, 2H, H-20 and H-60, J ¼ 8.3), 13.14 (s,
1H, NH), 14.31 (br. s, 1H, NH); 13C NMR (75 MHz, DMSO-d6):
The title compound was isolated as white powder (74%); mp
d
128.01 (C-40), 128.26 (C20 and C-60), 129.08 (C-30 and C-50), 135.32
271e273 ꢁC (acetic acid); ESI-MS m/z 314.0 (M ꢀ 1)þ; purity >95%;
(C-10), 141.08 (C-2), 151.46 (C-9), 160.89 (C-7), 175.22 (C-5); Anal.
calcd. for C10H6ClN5OS: C, 42.94; H, 2.16; N, 25.04. Found: C, 41.26;
H, 2.11; N, 24.29.
tR 2.23 min (B); 1H NMR (300 MHz, DMSO-d6): 7.82 (d, 1H, H-60,
d
J ¼ 8.3 Hz), 8.01 (dd,1H, H-50, J ¼ 8.3 Hz, J ¼ 1.9 Hz), 8.16 (d,1H, H-20,
J ¼ 1.9 Hz), 13.17 (s, 1H, NH), 14.35 (br. s, 1H, NH); 13C NMR (75 MHz,
DMSO-d6):
d
127.1 (C-60), 128.5 (C-20), 130.3 (C-50), 132.0 (C-40),
4.1.16. 2-(4-Bromophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo
[1,5-a][1,3,5]triazin-7(4H)-one (5l)
132.4 (C-30), 133.9 (C-10), 141.6 (C-2), 152.2 (C-9), 160.4 (C-7), 175.9
(C-5); Anal. calcd. for C10H5Cl2N5OS: C, 38.23; H, 1.60; N, 22.29.
Found: C, 38.02; H, 1.41; N, 21.95.
The title compound was isolated as white powder (73%); mp
292e293 ꢁC (acetic acid); ESI-MS m/z 324.0 (M ꢀ 1)þ; purity >95%;
tR 2.21 min (B); 1H NMR (300 MHz, DMSO-d6):
d
7.75 (d, 2H, H-30 and
4.1.22. 2-(3,4-Difluorophenyl)-5-thioxo-5,6-dihydro-[1,2,4]triazolo
[1,5-a][1,3,5]triazin-7(4H)-one (5r)
H-50, J ¼ 8.3), 7.98 (d, 2H, H-20 and H-60, J ¼ 8.3), 13.13 (s, 1H, NH),
14.35 (br. s, 1H, NH). 13C NMR (75 MHz, DMSO-d6):
d
124.8 (C-40),
The title compound was isolated as white powder (68%); mp
128.9 (C-10), 129.1 (C20 and C-60), 132.6 (C-30 and C-50), 141.7 (C-2),
152.0 (C-9), 161.6 (C-7), 175.8 (C-5); Anal. calcd. for C10H6BrN5OS: C,
37.05; H, 1.87; N, 21.60. Found: C, 36.54; H, 1.75; N, 20.82.
267e269 ꢁC (acetic acid); ESI-MS m/z 280.3 (M ꢀ 1)þ; purity >95%;
tR 2.16 min (B); 1H NMR (300 MHz, DMSO-d6):
d 7.57e7.66 (m, 1H,
H-50), 7.89e8.00 (m, 1H, H-20 and H-60), 13.17 (s, 1H, NH), 14.40 (br.