ISTREFI ET AL.
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1
J = 8.6 Hz), 7.68 (2H, d, ═CH, J = 8.8 Hz), 7.58 (2H, d, ═CH, J = 7.8 Hz),
1,655 (C═C), 1,322, and 1,152 (S═O; Figure S34); H NMR (300 MHz,
DMSO‐d ppm): 10.6–10.8 (2H, s, –NH), 7.76 (2H, d, ═CH,
J = 8.8 Hz), 7.68 (2H, d, ═CH, J = 8.8 Hz), 7.0–7.6 (4H, m, ═CH), 7.3
7
.31 (2H, d, ═CH, J = 7.9 Hz), 7.20 (2H, s, –NH
2
), and 4.1 (2H, s, –CH
, ppm): 170.2, 166.6, 141.9,
39.62, 138.4, 133.3, 132.8, 132, 127.5, 125.9, 119.6, 119.5, and 38.3
Figure S24). Anal. calcd. for C18 14BrN : C, 43.91; H, 2.87; Br,
6.23; N, 14.22; O, 9.75; S, 13.02. Found: C, 43.95; H, 2.89; Br, 16.28;
2
;
6
,
13
Figure S23); C NMR (75 MHz, DMSO‐d
6
1
3
1
(2H, s, –NH
DMSO‐d , ppm): 170.2, 166.64, 161.2, 141.9, 139.6, 131.7, 131.6,
127.5, 120, 119.6, 113.9, 113.6, 111.2, 110.9, and 35.4 (Figure S36).
Anal. calcd. for C18 14FN : C, 50.11; H, 3.27; F, 4.4; N, 16.23; O,
1.12; S, 14.86. Found: C, 50.18; H, 3.29; F, 4.47; N, 16.28; O, 11.17;
S, 14.89.
2 2
), and 4.1 (2H, s, –CH ; Figure S35); C NMR (75 MHz,
(
H
5
O S
3 2
6
1
N, 14.29; O, 9.79; S, 13.10.
H
5 3 2
O S
1
2
‐[1‐(4‐Chlorophenylamino)‐2,2‐dicyanovinylthio]‐N‐(4‐
sulfamoylphenyl)acetamide (7i)
−
1
Yield 79.9%, m.p. 188°C; IR (cm ): 3,260 (–NH
2
), 3,202 (–NH), 3,143
2‐[2,2‐Dicyano‐1‐(4‐fluorophenylamino)vinylthio]‐N‐(4‐
(═C–H, aromatic), 2,805 (–CH
2
, aliphatic), 2,220 (CN), 1,660 (C═O),
sulfamoylphenyl)acetamide (7m)
1
−1
1
,628 (C═C), 1,319, and 1,152 (S═O; Figure S25); H NMR (300 MHz,
2
Yield 78.5%, m.p. 212°C; IR (cm ): 3,271 (–NH ), 3,208 (–NH), 3,136
DMSO‐d
J = 8.6 Hz), 7.68 (2H, d, ═CH, J = 8.7 Hz), 7.32 (2H, d, ═CH, J = 8.1 Hz),
.28 (2H, d, ═CH, J = 8.1 Hz), 7.20 (2H, s, –NH ), and 4.1 (2H, s, –CH
, ppm): 170.2, 166.5, 141.9,
39.62, 138, 131.2, 129.9, 129.8, 127.5, 127.4, 125.5, 119.6, and 38.3
Figure S27). Anal. calcd. for C18 14ClN : C, 48.27; H, 3.15; Cl,
.92; N, 15.64; O, 10.72; S, 14.32. Found: C, 48.31; H, 3.19; Cl, 7.98;
6
,
ppm): 10.6–10.8 (2H, s, –NH), 7.76 (2H, d, ═CH,
(═C–H, aromatic), 2,988 (–CH
2
, aliphatic), 2,220 (CN), 1,660 (C═O),
1
1,622 (C═C), 1,319, and 1,151 (S═O; Figure S37); H NMR (300 MHz,
7
2
2
;
DMSO‐d
J = 8.7 Hz), 7.69 (2H, d, ═CH, J = 8.7 Hz), 7.20 (2H, d, ═CH, J = 8.4 Hz),
7.13 (2H, d, ═CH, J = 8.3 Hz), 7.3 (2H, s, –NH ), and 4.1 (2H, s, –CH
, ppm): 170.3, 166.6, 141.9,
139.6, 137.4, 127.5, 127.4, 126.8, 126.7, 119.6, 117, 116.6, and 37.98
(Figure S39). Anal. calcd. for C18 14FN : C, 50.11; H, 3.27; F,
.4; N, 16.23; O, 11.12; S, 14.86. Found: C, 50.16; H, 3.29; F, 4.45; N,
16.26; O, 11.19; S, 14.89.
6
, ppm): 10.6–10.8 (2H, s, –NH), 7.76 (2H, d, ═CH,
13
Figure S26); C NMR (75 MHz, DMSO‐d
6
1
2
2
;
1
3
(
H
5
O S
3 2
Figure S38); C NMR (75 MHz, DMSO‐d
6
7
N, 15.69; O, 10.75; S, 14.36.
H
5 3 2
O S
4
2
‐[2,2‐Dicyano‐1‐(2,4‐dichlorophenylamino)vinylthio]‐N‐(4‐
sulfamoylphenyl)acetamide (7j)
−1
Yield 79.9%, m.p. 207°C; IR (cm ): 3,308 (–NH
2
), 3,211 (–NH), 3,071
2‐[2,2‐Dicyano‐1‐(3‐(trifluoromethyl)phenylamino)vinylthio]‐N‐(4‐
(
═C–H, aromatic), 2,957 (–CH , aliphatic), 2,222 (CN), 1,662 (C═O),
2
sulfamoylphenyl)acetamide (7n)
1
−1
1
,621 (C═C), 1,331, and 1,149 (S═O; Figure S28); H NMR (300 MHz,
Yield 68.5%, m.p. 188°C; IR (cm ): 3,264 (–NH
2
), 3,200 (–NH),
6
DMSO‐d , ppm): 10.6–10.8 (2H, s, –NH), 7.77 (2H, d, ═CH, J = 8.8 Hz),
3,068 (═C–H, aromatic), 2,988 (–CH , aliphatic), 2,217 (CN),
2
7
4
1
1
.73 (2H, d, ═CH, J = 8.8 Hz), 7.4 (3H, m, ═CH), 7.20 (2H, s, –NH
2
), and
1,660 (C═O), 1,622 (C═C), 1,330, and 1,150 (S═O; Figure S40);
13
1
.1 (2H, s, –CH
2
; Figure S29); C NMR (75 MHz, DMSO‐d
6
, ppm):
6
H NMR (300 MHz, DMSO‐d , ppm): 10.6–10.8 (2H, s, –NH), 7.74
67.6, 141.8, 139.9, 133.4, 131.4, 130.2, 130.1, 129.6, 129.1 127.5,
27.4, 119.7, 119.6, and 38.2 (Figure S30). Anal. calcd. for
(2H, d, ═CH, J = 8.7 Hz), 7.67 (2H, d, ═CH, J = 8.6 Hz), 7.4 (4H, m,
1
3
═CH), 7.3 (2H, s, –NH
NMR (75 MHz, DMSO‐d
139.5, 131.2, 130.7, 127.8, 127.4, 126.2, 123.5, 122.6, 120.4,
19.5, 116.6, and 38.2 (Figure S42). Anal. calcd. for
: C, 47.4; H, 2.93; F, 11.84; N, 14.55; O, 9.97; S,
2
), and 4.1 (2H, s, –CH
2
; Figure S41);
C
C
18
H
13Cl
2
N
5
O
3
S
2
: C, 44.82; H, 2.72; Cl, 14.70; N, 14.52; O, 9.95; S,
6
, ppm): 170.69, 166.6, 141.9, 139.8,
13.29. Found: C, 44.88; H, 2.77; Cl, 14.74; N, 14.56; O, 9.99; S, 13.34.
1
2
‐[2,2‐Dicyano‐1‐(3,5‐dichlorophenylamino)vinylthio]‐N‐(4‐
19 14 3 5 3 2
C H F N O S
sulfamoylphenyl)acetamide (7k)
13.32. Found: C, 47.44; H, 2.98; F, 11.89; N, 14.58; O, 9.99;
S, 13.37.
−
1
2
Yield 70.9%, m.p. 235°C; IR (cm ): 3,275 (–NH ), 3,214 (–NH), 3,086
(═C–H, aromatic), 2,989 (–CH
2
, aliphatic), 2,216 (CN), 1,662 (C═O),
1
1
,621 (C═C), 1,317, and 1,160 (S═O; Figure S31); H NMR (300 MHz,
2‐[2,2‐Dicyano‐1‐(4‐iodophenylamino)vinylthio]‐N‐(4‐
sulfamoylphenyl)acetamide (7o)
DMSO‐d
6
, ppm): 10.6–10.8 (2H, s, –NH), 7.76 (2H, d, ═CH,
−
1
J = 8.4 Hz), 7.67 (2H, d, ═CH, J = 8.4 Hz), 7.2–7.6 (3H, ═CH), 7.4 (2H,
2
Yield 78.5%, m.p. 213°C; IR (cm ): 3,264 (–NH ), 3,205 (–NH),
1
3
s, –NH
ppm): 170.5, 166.06, 141.8, 139.64, 135.3, 135.1, 131.7, 129.1, 128.1,
27.5, 126.2, 122.3, 119.6, 113.1, and 39.3 (Figure S33). Anal. calcd.
for C18 13Cl : C, 44.82; H, 2.72; Cl, 14.70; N, 14.52; O, 9.95;
2
), 4.1 (2H, s, –CH
2
; Figure S32); C NMR (75 MHz, DMSO‐d
6
,
3,136 (═C–H, aromatic), 2,988 (–CH2, aliphatic), 2,219 (CN),
1,660 (C═O), 1,622 (C═C), 1,330, and 1,150 (S═O; Figure S43);
1
1
6
H NMR (300 MHz, DMSO‐d , ppm): 10.6–10.8 (2H, s, –NH), 7.75
H
N O
2 5 3
S
2
(2H, d, ═CH, J = 8.5 Hz), 7.67 (2H, d, ═CH, J = 8.5 Hz), 7.22 (2H, d,
S, 13.29. Found: C, 44.86; H, 2.77; Cl, 14.75; N, 14.58; O, 9.99;
S, 13.38.
═CH, J = 8.1 Hz), 7.00 (2H, d, ═CH, J = 8.1 Hz), 7.3 (2H, s, –NH ),
2
1
3
6
and 4.1 (2H, s, –CH2; Figure S44); C NMR (75 MHz, DMSO‐d ,
ppm): 170.1, 166.5, 141.9, 139.5, 139.4, 138.7, 138.6, 127.8,
127.5, 125.9, 119.6, 119.5, and 38.0 (Figure S45). Anal. calcd. for
2
‐[2,2‐Dicyano‐1‐(3‐fluorophenylamino)vinylthio]‐N‐(4‐
sulfamoylphenyl)acetamide (7l)
18 5 3 2
C H14IN O S : C, 40.08; H, 2.62; I, 23.53; N, 19.98; O, 8.9; S,
−
1
Yield 80.9%, m.p. 210°C; IR (cm ): 3,270 (–NH
2
), 3,200 (–NH), 3,086
11.89. Found: C, 40.18; H, 2.65; I, 23.55; N, 20.05; O, 8.94;
S, 11.93.
(
═C–H, aromatic), 2,889 (–CH , aliphatic), 2,209 (CN), 1,705 (C═O),
2