914
T. N. V. Ganesh Kumar et al.
Hexanoic acid (3-mercapto-5-pyrazin-2-yl-[1,2,4]tri-
(400 MHz, DMSO-d ; d, ppm): 7.30 – 7.42 (m, 2H),
6
azol-4-yl)-amide (6e): Yield 82%; mp 170 – 172°C; FTIR
(KBr; n, cm-1): 3300 (N-H, str.), 3163 (C-H, str.), 2956
7.96 – 8.00 (m, 2H), 8.64 – 8.65 (dd, J = 2.4 Hz and 1.6 Hz,
1H), 8.76 (d, J = 2.4 Hz, 1H), 9.177 (d, J = 1.6 Hz, 1H),
12.11 (s, 1H), 14.51 (s, 1H); GC/MS (EI, m/z) 316 (M)+.
4-Ethyl-N-(3-mercapto-5-pyrazin-2-yl-[1,2,4]triazol-
4-yl)-benzamide(6k):Yield 55%; mp 246 – 248°C; FTIR
(KBr; n, cm-1): 3068 (Ar-H, str.), 2960 (C-H, str.), 2682
1
(Ar-H, str.), 2605 (S-H, str.), 1714 (C=O, str.); H NMR
(400 MHz, DMSO-d ; d, ppm): 0.84 (t, J = 7.2Hz, 3H),
6
1.18 – 1.27 (m, 4H), 1.46 – 1.54 (m, 2H), 2.26 (t, J = 7.2 Hz,
2H), 8.74 (d, 1.6 Hz, 1H), 8.80 (d, J = 2.4 Hz, 1H), 9.09 (s,
1H), 11.44 (s, 1H), 14.38 (s, 1H); 13C NMR (100 MHz,
(S-H, str.), 1691 (C=O, str.); 1H NMR (400 MHz, DMSO-d ;
6
DMSO-d ; d, ppm): 14.29, 22.23, 24.74, 31.00, 33.41,
d, ppm): 1.22 (t, J = 7.6 Hz, 3H), 2.65 – 2.71 (dd,
J = 15.2 Hz and 7.6 Hz, 2H), 7.39 (d, J = 8 Hz, 2H), 7.84 (d,
J = 8 Hz, 2H), 8.65 – 8.66 (dd, J = 2.4 Hz and 1.6 Hz, 1H),
8.76 (d, J = 2.4 Hz, 1H), 9.16 (d, J = 1.6 Hz, 1H), 11.96 (s,
6
140.97, 143.99, 144.80, 146.69, 147.69, 169.37, 171.63.
LCMS (ESI, m/z) 294.88 (M+H)+.
Heptanoic acid (3-mercapto-5-pyrazin-2-yl-[1,2,4]tri-
azol-4-yl)-amide (6f): Yield 77%; mp 182 – 184°C; FTIR
(KBr; n, cm-1): 3348 (N-H, str.), 3153 (C-H, str.), 2956
1H), 14.47 (s, 1H); 13C NMR (100 MHz, DMSO-d ; d, ppm):
6
15.74, 28.62, 128.57, 129.15, 140.96, 143.89, 144.90,
145.15, 146.10, 146.73, 147.38, 149.50, 164.65, 165.64,
169.70. GC/MS (EI, m/z) 326 (M)+.
1
(Ar-H, str.), 2370 (S-H, str.), 1680 (C=O, str.); H NMR
(400 MHz, DMSO-d ; d, ppm): 0.85 (t, J = 6.8 Hz, 3H),
6
4-Ethoxy-N-(3-mercapto-5-pyrazin-2-yl-[1,2,4]triazol-
4-yl)-benzamide(6l):Yield 77%; mp 258 – 260°C; FTIR
(KBr; n, cm-1): 3347 (N-H, str.), 2989 (Ar-H, str.), 2466
(S-H, str.), 1691 (C=O, str.), 1269 (Assym. C-O-C, str.), 873;
1.51(t, J = 6.8 Hz, 2H), 1.21 – 1.24 (m, 6H), 2.26 (t,
J = 7.2 Hz, 2H), 8.74 (dd, J = 2.4 Hz and 1.6 Hz, 1H), 8.80
(d, J = 1.6 Hz, 1H), 9.09 (d, J = 1.6 Hz, 1H), 11.46 (s, 1H),
14.37 (s, 1H); 13C NMR (100 MHz, DMSO-d ; d, ppm):
6
1H NMR (400 MHz, DMSO-d ; d, ppm): 1.36 (t, J = 7.2 Hz
14.37, 22.42, 25.03, 29.50, 31.37, 33.47, 140.97, 143.99,
144.79, 146.69, 147.31, 169.38, 171.63. GC/MS (EI, m/z)
306 (M)+.
6
and 14 Hz, 3H), 4.08 – 4.14 (dd, J = 7.2 Hz and 14 Hz, 2H),
7.06 (d, J = 8.8 Hz, 2H), 7.85 – 7.88 (m, 2H), 8.64 – 8.65
(dd, J = 2.4 Hz and 1.6 Hz, 1H), 8.75 (d, J = 2.4 Hz, 1H),
9.14 (d, J = 1.6 Hz, 1H), 11.86 (s, 1H), 14.45 (s, 1H); 13C
N-(3-Mercapto-5-pyrazin-2-yl-[1,2,4]triazol-4-yl)-2-me-
thyl-benzamide (6g): Yield 74%; mp 250 – 252°C; FTIR
(KBr; n, cm-1): 3390 (N-H, str.), 3032 (Ar-H, str.), 1707
NMR (100 MHz, DMSO-d ; d, ppm): 14.95, 63.82, 15.33,
6
(C=O, str.); 13CNMR (100 MHz, DMSO-d ; d, ppm): 19.56,
117.09, 129.43, 143.09, 144.46, 144.53, 149.50, 150.93,
161.01, 162.56, 168.32. GC/MS (EI, m/z) 342 (M)+.
6
126.17, 128.21, 131.19, 133.45, 136.94, 141.00, 144.00,
144.81, 146.81, 147.13, 167.79, 169.62. GC/MS (EI, m/z)
312 (M)+.
N-(3-Mercapto-5-pyrazin-2-yl-[1,2,4]triazol-4-yl)-3,4-
dimethoxy-benzamide (6m): Yield 64%; mp 276 – 280°C;
FTIR (KBr; n, cm-1): 3080 (Ar-H, str.), 3034 (C-H, str.),
2364 (S-H, str.), 1680 (C=O, str.), 1253 (Assym. C-O-C,
str.), 1134 (Sym. C-O-C, str.); 1H NMR (400 MHz,
N-(3-Mercapto-5-pyrazin-2-yl-[1,2,4]triazol-4-yl)-3-me-
thoxy-benzamide (6h): Yield 91%; mp 256 – 258°C; FTIR
(KBr; n, cm-1): 3385 (N-H, str.), 3099 (Ar-H, str.), 3034
(C-H, str.), 1685 (C=O, str.); 1H NMR (400 MHz,
DMSO-d ; d, ppm): 3.78 – 3.83 (m, 6H), 7.11 (d, J = 8.4 Hz,
6
1H), 7.45 (d, J = 2 Hz, 1H), 7.59 (dd, J = 8.4 Hz and 2 Hz,
1H), 8.65 – 8.66 (dd, J = 2.4 Hz and 1.6 Hz, 1H), 8.76 (d,
J = 2.4 Hz, 1H), 9.15 (d, J = 1.6 Hz, 1H), 11.88 (s, 1H),
14.46 (s, 1H); LCMS (ESI, m/z) 359.07 (M+H)+.
DMSO-d ): d3.81 (s, 3H), 7.19 – 7.22 (m, 1H), 7.42 – 7.44
6
(m, 1H), 7.46 – 7.50 (m, 2H), 8.66 – 8.67 (dd, J = 2.4 Hz and
1.6 Hz, 1H), 8.76 (d, J = 2.4 Hz, 1H), 9.17 (d, J = 1.6 Hz,
1H), 12.03 (s, 1H), 14.49 (s, 1H); GC/MS (EI, m/z) 328
(M)+.
Pyrazine-2-carboxylic acid (3-mercapto-5-o-tolyl-[1,2,4]-
triazol-4-yl)-amide (11a): Yield 39%; mp 242 – 244°C;
FTIR (KBr; n, cm-1): 3340 (N-H, str.), 3145 (Ar-H, str.),
2895 (C-H, str.), 2360 (S-H, str.), 1741 (C=O, str.); 1H NMR
N-(3-Mercapto-5-pyrazin-2-yl-[1,2,4]triazol-4-yl)-4-
methoxy-benzamide (6i): Yield 48%; mp 266 – 268°C;
FTIR (KBr; n, cm-1): 3338 (N-H, str.), 2960 (Ar-H, str.),
2681 (S-H, str.), 1693 (C=O, str.), 1290 (Assym. C-O-C,
(400 MHz, DMSO-d ; d, ppm): 2.30 (s, 3H), 7.29 – 7.31 (m,
6
1
str.); H NMR (400 MHz, DMSO-d ; d, ppm): 3.81 (s, 3H),
1H), 7.43 – 7.46 (m, 1H) 7.66 (d, J = 8 Hz, 2H), 8.86 (dd,
J = 2.4 Hz and 1.6 Hz, 1H), 8.99 (d, J = 2.4 Hz, 1H), 9.183
(d, J = 1.2Hz, 1H), 12.36 (s, 1H), 14.14 (s, 1H); GC/MS (EI,
m/z) 312 (M)+.
6
7.04 (d, J = 8.8 Hz, 2H); 7.72 (d, J = 8.8 Hz, 2H), 8.87 – 8.88
(dd, J = 2.4 Hz and 1.6 Hz, 1H), 9.00 (d, J = 2.4 Hz, 1H),
9.20 (d, J = 1.6 Hz, 1H), 12.29 (s, 1H), 14.09 (s, 1H); 13C
Pyrazine-2-carboxylic acid (3-mercapto-5-p-tolyl-
[1,2,4]triazol-4-yl)-amide (11b): Yield 37%; mp 240 –
241°C; FTIR (KBr; n, cm-1): 2995 (C-H, str.), 2360 (S-H,
NMR (100 MHz, DMSO-d ; d, ppm): 55.87, 113.29, 119.05,
6
120.46, 130.46, 133.00, 140.92, 143.89, 144.90, 146.77,
147.25, 159.78, 165.52, 169.69. GC/MS (EI, m/z) 328 (M)+.
4-Fluoro-N-(3-mercapto-5-pyrazin-2-yl-[1,2,4]triazol-
4-yl)-benzamide (6j): Yield 61%; mp 244 – 246°C; FTIR
(KBr; n, cm-1): 3340 (N-H, str.), 3039 (Ar-H, str.), 2964
1
str.), 1716 (C=O, str.); H NMR (400 MHz, DMSO-d ; d,
6
ppm): 2.30 (s, 3H), 7.29 (d, J = 8 Hz, 2H) 7.66 (d, J = 8 Hz,
2H), 8.86 (dd, J = 2.4 Hz and 1.6 Hz, 1H), 8.99 (d,
J = 2.4 Hz, 1H), 9.183 (d, J = 1.2Hz, 1H), 12.30 (s, 1H),
1
(C-H, str.), 2360 (S-H, str.), 1697 (C=O, str.); H NMR