14 of 18
PATHAK ET AL.
|
NO
2
–Ph), 7.630–7.604 (d, 2H, J = 7.8 Hz, Br–Ph), 8.121–8.092 (d, 2H,
NMR (100 MHz, CDCl
3
) δ ppm: 33.89, 49.27, 66.24, 72.7, 123.98,
13
J = 8.7 Hz, NO
2
–Ph), 8.876 (s, 1H, NH), 9.134 (s, 1H, NH); C NMR
126.2, 127.82, 128.71, 130.66, 133.16, 134.10, 136.92, 145.2,
+
(
100 MHz, CDCl ) δ ppm: 17.8, 44.31, 49.27, 66.24, 72.75, 117.29,
3
147.98, 149.65, 165.8, 167.26; MS‐ESI (m/z): 507.45 [M+H] ; ele-
1
1
24.02, 126.2, 127.82, 128.1, 130.95, 136.95, 140.47, 145.2, 165.8,
mental analysis: calculated C: 44.93%, H: 3.57%, N: 19.30%; found C:
44.5%, H: 3.42%, N: 19.75%.
+
67.26; MS‐ESI (m/z): 565.52 [M+H] ; elemental analysis: calculated
C: 42.41%, H: 3.56%, N: 17.31%; found C: 42.5%, H: 3.75%,
N: 17.52%.
2‐{[2‐(2‐Chlorophenyl)‐4‐oxothiazolidin‐3‐yl]amino}‐N‐[3‐(4‐
chlorophenyl)‐5‐mercapto‐1,5‐dihydro‐4H‐1,2,4‐triazol‐4‐yl]‐
acetamide (10i)
2
‐{[2‐(4‐Bromophenyl)‐5‐methyl‐4‐oxothiazolidin‐3‐yl]amino}‐N‐[3‐
(
4‐chlorophenyl)‐5‐mercapto‐1,5‐dihydro‐4H‐1,2,4‐triazol‐4‐yl]‐
White solid; yield: 76%; molecular formula:
melting point: 241–243°C; molecular weight: 497.41; H NMR
(300 MHz, CDCl , TMS) δ ppm: 1.524 (s, 1H, SH), 3.602–3.562 (d, 1H,
J = 12.0 Hz, CH , thiazolidine), 3.802–3.762 (d, 1H, J = 12.0 Hz, CH
thiazolidine), 3.953 (s, 2H, CH ), 6.296 (s, 1H, CH, thiazolidine), 4.243
19 2 6 2 2
C H18Cl N O S ;
1
acetamide (10f)
Yellow solid; yield: 76%; molecular formula: C20
H
20BrClN
1
6
O
2
S
2
;
3
melting point: 241–243°C; molecular weight: 555.89; H NMR
2
2
,
(
300 MHz, CDCl
.524 (s, 1H, SH), 3.953 (s, 2H, CH
thiazolidine), 4.243 (s, 1H, NH), 6.296 (1H, s, CH, thiazolidine), 6.463
s, 1H, CH, triazole), 7.16–7.135 (d, 2H, J = 7.5 Hz, Br–Ph),
.630–7.605 (d, 2H, J = 7.5 Hz, Br–Ph), 7.674–7.648 (d, 2H,
J = 7.8 Hz, Cl–Ph), 7.921–7.892 (d, 2H, J = 8.7 Hz, Cl–Ph), 8.876 (s,
3
, TMS) δ ppm: 1.264–1.241 (d, 3H, J = 6.9 Hz, CH
3
),
2
1
2
), 4.092 (m, 1H, J = 7.0 Hz, CH,
(s, 1H, NH), 6.463 (s, 1H, CH, triazole), 7.215 (m, 1H, Ph–Cl), 7.334
(m, 1H, Ph–Cl), 7.398–7.373 (d, 2H, J = 7.5 Hz, Cl–Ph), 7.425–7.41 (d,
2H, J = 7.5 Hz, Cl–Ph), 7.524 (m, 1H, Cl–Ph), 7.921–7.892 (d, 2H,
(
13
7
J = 8.7 Hz, Cl–Ph), 8.872 (s, 1H, NH), 9.132 (s, 1H, NH); C NMR
(100 MHz, CDCl ) δ ppm: 33.89, 49.27, 66.24, 72.7, 126.2, 127.82,
3
1
3
1
4
1
H, NH), 9.134 (s, 1H, NH); C NMR (100 MHz, CDCl
3
) δ ppm: 17.8,
128.09, 128.71, 129.08, 130.66, 133.16, 135.68, 136.92, 145.2,
+
4.31, 49.27, 66.24, 72.5, 117.29, 124.02, 126.2, 127.82, 128.52,
149.62, 165.8, 167.26; MS‐ESI (m/z): 496.52 [M+H] ; elemental
30.95, 136.95, 140.47, 145.2, 165.8, 167.26; MS‐ESI (m/z): 554.10
analysis: calculated C: 45.88%, H: 3.65%, N: 16.90%; found C:
+
[
M+H] ; elemental analysis: calculated C: 43.21%, H: 3.63%, N:
45.58%, H: 3.78%, N: 16.70%.
1
5.12%; found C: 43.4%, H: 3.52%, N: 15.24%.
2‐{[2‐(2‐Chlorophenyl)‐5‐methyl‐4‐oxothiazolidin‐3‐yl]amino}‐N‐[5‐
2
3
‐{[2‐(2‐Chlorophenyl)‐4‐oxothiazolidin‐3‐yl]amino}‐N‐[5‐mercapto‐
‐(pyridin‐4‐yl)‐1,5‐dihydro‐4H‐1,2,4‐triazol‐4‐yl]acetamide (10 g)
mercapto‐3‐(pyridin‐4‐yl)‐1,5‐dihydro‐4H‐1,2,4‐triazol‐4‐yl]‐
acetamide (10j)
Brown solid; yield: 71%; molecular formula: C18
H
1
18ClN
7
O
2
S
2
; melt-
Reddish‐yellow
solid;
melting point: 243–245°C; molecular weight:
, TMS) δ ppm: 1.241–1.264 (d, 3H,
), 1.524 (s, 1H, SH), 3.953 (s, 2H, CH ), 4.092 (m, 1H,
yield:
72%;
molecular
formula:
ing point: 176–178°C; molecular weight: 463.96; H NMR (300 MHz,
C
19
H
20ClN
1
7 2 2
O S ;
CDCl
J = 12.0 Hz, CH
thiazolidine), 3.953 (s, 2H, CH
thiazolidine), 6.463 (s, 1H, CH, triazole), 7.215 (m, 1H, Ph–Cl), 7.334
m, 1H, Ph–Cl), 7.524 (m, 1H, Cl–Ph), 7.664–7.651 (d, 2H, J = 3.9 Hz,
CH, pyridine), 7.921–7.892 (d, 2H, J = 8.7 Hz, Cl–Ph), 8.679–8.664 (d,
3
, TMS) δ ppm: 1.524 (s, 1H, –SH), 3.602–3.562 (d, 1H,
, thiazolidine), 3.802–3.762 (d, 1H, J = 12.0 Hz, CH
), 4.243 (s, 1H, NH), 6.296 (s, 1H, CH,
477.99; H NMR (300 MHz, CDCl
3
2
2
,
J = 7.0 Hz, CH
3
2
2
CH, thiazolidine), 4.243 (s, 1H, NH), 6.213 (s, 1H, CH, triazole), 6.296
(s, 1H, CH, thiazolidine), 6.463 (s, 1H, CH, triazole), 7.215–7.19 (m,
1H, Ph–Cl), 7.334–7.303 (m, 1H, Ph–Cl), 7.524 (m, 1H, Cl–Ph),
7.664–7.649 (d, 2H, J = 4.5 Hz, CH, pyridine), 7.921–7.892 (d, 2H,
J = 8.7 Hz, Cl–Ph), 8.679–8.664 (d, 2H, J = 4.5 Hz, CH, pyridine),
(
13
2
H, J = 4.5 Hz, CH, pyridine), 8.876 (s, 1H, NH), 9.134 (s, 1H, NH);
C
13
NMR (100 MHz, CDCl
3
) δ ppm: 33.89, 49.27, 66.24, 72.15, 121.33,
3
8.876 (s, 1H, NH), 9.134 (s, 1H, NH); C NMR (100 MHz, CDCl ) δ
1
1
26.8, 127.82, 128.71, 130.66, 133.16, 134.10, 136.92, 145.2,
ppm: 17.8, 44.31, 49.27, 66.24, 72.7, 121.33, 122.2, 126.80, 127.82,
+
49.65, 165.8, 167.26; MS‐ESI (m/z): 463.42 [M+H] ; elemental
128.71, 130.66, 133.16, 136.92, 145.2, 149.65, 165.8, 167.26; MS‐
+
analysis: calculated C: 46.60%, H: 3.91%, N: 21.13%; found C:
6.25%, H: 3.92%, N: 21.2%.
ESI (m/z): 477.82 [M+H] ; elemental analysis: calculated C: 47.74%,
4
H: 4.22%, N: 20.51%; found C: 47.8%, H: 4.28%, N: 20.42%.
2
3
‐{[2‐(2‐Chlorophenyl)‐4‐oxothiazolidin‐3‐yl]amino}‐N‐[5‐mercapto‐
‐(4‐nitrophenyl)‐1,5‐dihydro‐4H‐1,2,4‐triazol‐4‐yl]acetamide (10h)
2‐{[2‐(2‐Chlorophenyl)‐5‐methyl‐4‐oxothiazolidin‐3‐yl]amino}‐N‐[5‐
mercapto‐3‐(4‐nitrophenyl)‐1,5‐dihydro‐4H‐1,2,4‐triazol‐4‐yl]‐
acetamide (10k)
Yellow solid; yield: 74%; molecular formula: C19
H
7
18ClN O
4
S
2
; melt-
ing point: 255°C; molecular weight: 507.97; H NMR (300 MHz,
CDCl , TMS) δ ppm: 1.524 (s, 1H, SH), 3.602–3.562 (d, 1H,
J = 12.0 Hz, CH , thiazolidine), 3.802–3.762 (d, 1H, J = 12.0 Hz, CH
thiazolidine), 3.953 (s, 2H, CH ), 6.296 (s, 1H, CH, thiazolidine), 4.243
1
Brown solid; yield: 79%; molecular formula: C20
H
20ClN
7
O
4
S
2
; melt-
ing point: 237–235°C; molecular weight: 522; H NMR (300 MHz,
CDCl , TMS) δ ppm: 1.241–1.264 (d, 3H, J = 7.0 Hz, CH ), 1.524 (s,
1H, SH), 3.953 (s, 2H, CH ), 4.092 (m, 1H, CH, thiazolidine), 4.243 (s,
1
3
2
2
,
3
3
2
2
(
s, 1H, NH), 6.463 (s, 1H, CH, triazole), 7.215 (m, 1H, Ph–Cl), 7.334
m, 1H, Ph–Cl), 7.524 (m, 1H, Cl–Ph), 7.921–7.892 (d, 2H, J = 8.7 Hz,
1H, NH), 6.296 (s, 1H, CH, thiazolidine), 6.463 (s, 1H, CH, triazole),
7.215 (m, 1H, Ph–Cl), 7.334 (m, 1H, Ph–Cl), 7.524 (m, 1H, Cl–Ph),
7.921–7.892 (d, 2H, J = 8.7 Hz, Cl–Ph), 8.12–8.092 (d, 2H, J = 8.4 Hz,
(
Cl–Ph), 8.12–8.092 (d, 2H, J = 8.4 Hz, NO
2
–Ph), 8.489–8.462 (d, 2H,
13
J = 8.1 Hz, CH, NO –Ph), 8.872 (s, 1H, NH), 9.132 (s, 1H, NH);
2
C
2 2
NO –Ph), 8.489–8.462 (d, 2H, J = 8.1 Hz, CH, NO –Ph), 8.872 (s, 1H,