LI ET AL.
9
ꢀ
1
1
8
15-119 C. H NMR (CDCl ) δ 8.75 (d, J = 1.3 Hz, 1H),
J = 19.9 Hz), 38.72, 20.69. HRMS (EI): C H ClF N O S
13 15 2 6 4 2
(M) calcd. 457.0253; found 457.0256.
3
+
.62 (s, 1H), 8.58 (dd, J = 4.7, 1.3 Hz, 1H), 8.03 (d,
J = 8.0 Hz, 1H), 7.74 (s, 1H), 7.34-7.27 (m, 1H), 3.57 (s,
Methyl(E)-2-((6-chloropyridin-2-yl)methylene)-1-((1-(N,
N-dimethylsulfamoyl)-1H-1,2,4-triazol-3-yl)sulfonyl)hydra-
zine-1-carboxylate (8q). White solid (64%). Melting points:
13
3
H), 3.01 (s, 6H). C NMR: δ 160.82, 154.07, 150.36,
1
48.86, 146.72, 142.84, 135.08, 124.93, 38.75, 34.91.
+
ꢀ
1
HRMS (EI): C H N O S (M) calcd. 374.0627; found
132-136 C. H NMR (CDCl ) δ 13.79 (s, 1H), 8.75 (d,
11
15
7
4 2
3
3
74.0625.
E)-3-((2-((2-chloropyridin-3-yl)methylene)-1-methy-
J = 8.5 Hz, 1H), 8.58 (dd, J = 4.7, 1.4 Hz, 1H), 7.85 (dd,
(
J = 8.2, 1.5 Hz, 1H), 7.32 (dd, J = 8.2, 4.7 Hz, 1H), 3.91 (s,
13
lhydrazinyl)sulfonyl)-N,N-dimethyl-1H-1,2,4-triazole-1-sul-
3H), 2.99 (s, 6H). C NMR: δ160.76, 151.74, 149.46,
fonamide (8l). White solid (42%). Melting points:
148.82, 141.84, 137.04, 129.73, 125.22, 108.34, 38.73,
ꢀ
1
+
1
20-125 C. H NMR (CDCl ) δ 8.62 (s, 1H), 8.40 (dd,
34.77. HRMS (EI): C H ClN O S (M) calcd. 452.0136;
3
12 14
7 6 2
J = 4.6, 1.8 Hz, 1H), 8.27 (dd, J = 7.8, 1.7 Hz, 1H), 7.98 (s,
found 452.0132.
13
1
H), 7.28 (t, J = 6.2 Hz, 1H), 3.62 (s, 3H), 3.05 (s, 6H).
C
Methyl(E)-1-((1-(N,N-dimethylsulfamoyl)-1H-
NMR: δ 160.69, 151.52, 149.78, 148.89, 139.79, 136.59,
1,2,4-triazol-3-yl)sulfonyl)-2-(naphthalen-1-ylmethylene)
hydrazine-1-carboxylate (8r). White solid (57%). Melting
+
1
28.49, 38.76, 34.78. HRMS (EI): C H ClN O S (M)
11 14 7 4 2
ꢀ
1
calcd. 408.0237; found 408.0235.
points: 138-142 C. H NMR (CDCl ) δ 9.97 (s, 1H), 8.75
3
(
E)-3-((2-((6-chloropyridin-3-yl)methylene)-
-methylhydrazinyl)sulfonyl)-N,N-dimethyl-1H-1,2,4-tri-
azole-1-sulfonamide (8m). White solid (57%). Melting
(d, J = 8.5 Hz, 1H), 8.47 (s, 1H), 7.93 (d, J = 8.1 Hz, 2H),
1
7.89 (d, J = 7.1 Hz, 1H), 7.64 (t, J = 7.6 Hz, 1H), 7.56 (dt,
13
J = 20.7, 7.7 Hz, 2H), 2.99 (s, 6H), 2.41 (s, 3H). C NMR:
δ162.13, 154.51, 144.20, 133.99, 130.51, 130.11, 129.21,
127.56, 126.65, 125.98, 124.47, 116.98, 112.47, 52.49,
ꢀ
1
points: 124-128 C. H NMR (CDCl ) δ 8.61 (s, 1H), 8.52
d, J = 2.0 Hz, 1H), 8.05 (dd, J = 8.4, 2.3 Hz, 1H), 7.71 (s,
3
(
+
1
H), 7.35 (d, J = 8.4 Hz, 1H), 3.58 (s, 3H), 3.05 (s, 6H).
C NMR: δ 160.76, 151.74, 149.46, 148.82, 141.84, 137.04,
29.73, 125.22, 38.73, 34.77. HRMS (EI): C H ClN O S
38.72, 14.56. HRMS (EI): C H N O S (M) calcd.
17
18 6 6 2
13
467.0729; found 467.0725.
1
Methyl(E)-2-((6-chloropyridin-2-yl)methylene)-1-((1-(N,
N-dimethylsulfamoyl)-1H-1,2,4-triazol-3-yl)sulfonyl)hydra-
zine-1-carboxylate (8s). White solid (47%). Melting points:
11
14
7
4 2
+
(
M) calcd. 408.0237; found 408.0235.
Z)-3-((2-((1H-indol-4-yl)methylene)-1-methylhydra-
zinyl)sulfonyl)-N,N-dimethyl-1H-1,2,4-triazole-1-sulfon-
(
ꢀ
1
128-133 C. H NMR (CDCl ) δ 13.79 (s, 1H), 8.75
3
ꢀ
amide (8n). White solid (42%). Melting points: 114-118 C.
H NMR (CDCl ) δ 11.21 (s, 1H), 9.37 (s, 1H), 8.36 (d,
J = 7.3 Hz, 1H), 8.24 (s, 2H), 7.91 (d, J = 8.3 Hz, 1H), 7.42
(d, J = 8.5 Hz, 1H), 8.58 (dd, J = 4.7, 1.4 Hz, 1H), 7.85
1
(dd, J = 8.2, 1.5 Hz, 1H), 7.32 (dd, J = 8.2, 4.7 Hz, 1H),
3
13
3.91 (s, 3H), 2.99 (s, 6H). C NMR: δ160.76, 151.74,
(
2
t, J = 7.5 Hz, 1H), 7.22 (t, J = 7.5 Hz, 1H),3.72 (s, 3H),
.81 (s, 6H). C NMR: δ 163.97, 162.33, 160.89, 148.78,
149.46, 148.82, 141.84, 137.04, 129.73, 125.22, 108.34,
13
+
38.73, 34.77. HRMS (EI): C H ClN O S (M) calcd.
12
14
7 6 2
1
44.27, 140.72, 129.99, 128.87, 117.97, 113.67, 34.82.
452.0136; found 452.0138.
+
HRMS (EI): C H N O S (M) calcd. 412.0783; found
Methyl(E)-2-((2,5-dichloropyridin-3-yl)methylene)-1-
((1-(N,N-dimethylsulfamoyl)-1H-1,2,4-triazol-3-yl)sulfonyl)
hydrazine-1-carboxylate (8t). White solid (35%). Melting
14
17 7 4 2
4
12.0784.
Z)-N,N-dimethyl-3-((1-methyl-2-(6-nitro-4H-chromen-
(
ꢀ
1
4
-ylidene)hydrazinyl)sulfonyl)-1H-1,2,4-triazole-1-sulfon-
points: 136-139 C. H NMR (CDCl ) δ 13.79 (s, 1H), 8.75
3
ꢀ
amide (8o). White solid (46%). Melting points: 132-137 C.
(d, J = 8.5 Hz, 1H), 8.58 (dd, J = 4.7, 1.4 Hz, 1H), 7.32
(dd, J = 8.2, 4.7 Hz, 1H), 3.91 (s, 3H), 2.99 (s, 6H).
1
13
H NMR (CDCl ) δ 8.58 (s, 1H), 7.74 (s, 1H), 7.69 (s, 1H),
C
3
7
2
1
.64 (s, 1H), 7.62 (dd, J = 7.1, 2.1 Hz, 2H), 3.32 (m, 3H),
.95 (s, 6H). C NMR: δ 169.92, 161.43, 148.35, 141.11,
NMR: δ163.76, 152.74, 145.46, 141.82, 137.04, 129.73,
13
123.22, 105.34, 39.73, 35.77. HRMS (EI): C H C N O S
12
13 l2 7 6 2
+
32.66, 130.47, 127.65, 127.17, 61.30, 39.06, 38.52, 36.87.
(M) calcd. 485.9746; found 485.9748.
+
HRMS (EI): C H N O S (M) calcd. 458.0474; found
(E)-3-((2-(2-bromobenzylidene)-1-(6-chloropyridin-2-yl)
hydrazinyl)sulfonyl)-N,N-dimethyl-1H-1,2,4-triazole-1-sul-
fonamide (8u). White solid (41%). Melting points:
14
15 7 7 2
4
58.0477.
E)-3-((2-(1-(2-chloro-4,5-difluorophenyl)ethylidene)-
-methylhydrazinyl)sulfonyl)-N,N-dimethyl-1H-1,2,4-tri-
(
ꢀ
1
1
141-143 C. H NMR (CDCl ) δ 8.69 (s, 1H), 8.04 (d,
3
azole-1-sulfonamide (8p). White solid (53%). Melting
J = 9.2 Hz, 1H), 8.00 (s, 1H), 7.94 (t, J = 7.8 Hz, 1H), 7.65
(d, J = 7.7 Hz, 1H), 7.53 (d, J = 8.1 Hz, 1H), 7.46 (d,
J = 7.9 Hz, 1H), 7.35 (t, J = 7.4 Hz, 1H), 7.30-7.23 (m,
1H), 2.98 (s, 6H). C NMR: δ162.13, 154.51, 144.20,
133.99, 130.51, 130.11, 129.21, 127.56, 126.65, 125.98,
ꢀ
1
points: 115-118 C. H NMR (CDCl ) δ 8.69 (s, 1H), 7.34
3
(
3
1
dd, J = 9.9, 8.4 Hz, 1H), 7.26 (dd, J = 10.3, 7.7 Hz, 1H),
.23 (s, 3H), 3.07 (s, 6H), 2.59 (s, 3H). C NMR: δ 174.45,
64.26159.26, 151.07 (d, J = 13.4 Hz), 149.44 (t,
13
13
J = 13.3 Hz), 148.62, 147.84 (d, J = 12.5 Hz), 126.90 (dd,
J = 8.9, 3.2 Hz), 120.02 (d, J = 20.8 Hz), 119.08 (d,
124.47, 116.98, 112.47, 52.49, 38.72. HRMS (EI):
+
C H BrClN O S (M) calcd. 547.9499; found 547.9497.
16
15
7 4 2