6
336 Shahid et al.
Asian J. Chem.
N-(2-Aminoethyl)-4,5-dimethoxy-2-(3-oxo-3-phenyl-
prop-1-en-1-yl)benzenesulfonamide (6b): Off-white crystal-
N'-(3,5-Dinitrophenyl)-4,5-dimethoxy-2-(3-oxo-3-
phenylprop-1-en-1-yl)benzenesulfonohydrazide (6h): Light
-1
-1
red solid, m.p. 275 ºC. IR (KBr, νmax, cm ): 1449.54, 1653.71,
line solid, m.p. 209-211 ºC. IR (KBr, νmax, cm ): 1408.56,
1
1
1105.28, 3544.98. H NMR (DMSO-d
1
3
5
7
624.20, 3551.13. H NMR (DMSO-d
.86 (s, 3H, OCH ), 4.01 (s, 2H, NH ), 4.73-4.79 (m, 2H, CH
.30 (s, 1H, NH), 6.69-6.72 (m, 2H, CH
.45 (s, 1H, ArH), 7.49 (d, 1H, J = 15.6, C=CH), 7.66-7.69
m, 5H, ArH), 8.80 (d, 1H, J = 15.6, HC=C) MS
6
) δ: 3.75 (s, 3H, OCH
3
),
6 3
) δ: 3.77 (s, 3H, OCH ),
3
2
2
),
3
3.89 (s, 3H, OCH ), 5.34 (s, 1H, NH),7.41 (s, 1H, ArH), 7.48
2
), 7.37 (s, 1H, ArH),
(s, 1H, ArH), 7.51(d, 1H, J = 15.6, C=CH), 7.56 (s, 1H, ArH),
8.80 (d, 1H, J = 15.6, HC=C), 7.59-7.64 (m, 2H, ArH), 8.11-
+
8.17 (m, 5H, ArH), 9.32(s, 1H, NH). MS m/z: 528 [M ].Anal.
(
+
m/z: 390 [M ].Anal. calcd. (%) for C19
.68; N, 7.17; Found (%): C, 58.48; H, 5.66; N, 7.20.
-[4,5-Dimethoxy-2-(3-oxo-3-phenylprop-1-en-1-yl)-
phenylsulfonamido]benzoic acid (6c): Light Green crystals;
22 2 5
H N O S: C, 58.45; H,
20 4 9
calcd. (%) for C23H N O S: C, 52.27; H, 3.81; N, 10.60; found
5
(%): C, 52.24; H, 3.82; N, 10.66.
2-[(4,5-Dimethoxy-2-(3-oxo-3-phenylprop-1-en-1-
yl)phenyl)sulfonyl]hydrazinecarboxamide (6i): Orange
2
-1
1
-1
crystalline solid, m.p. 197 ºC. IR (KBr, νmax, cm ): 1408.83,
m.p. 190 ºC. IR (KBr, νmax, cm ): 1420, 1637, 3547, 3595. H
NMR (DMSO) δ: 3.77 (s, 3H, OCH ),3.89 (s, 3H, OCH ),
.30 (s, 1H, NH), 7.44 (s, 1H,ArH), 7.50 (s, 1H, ArH), 7.55 (t,
H, J = 7.6, ArH), 7.58 (d, J = 15.6, 1H, C=CH), 7.69-7.73
1
1661.24, 3540. H NMR (DMSO-d
3
3
6
) δ: 3.78 (s, 3H, OCH
3
),
5
1
3.85 (s, 3H, OCH
(s, 1H, ArH), 7.47 (s, 1H, ArH), 7.48(d, 1H, J = 15.6, C=CH),
7.65-7.67 (m, 5H, ArH), 8.83 (d, 1H, J = 15.6, HC=C), 9.34
3
), 4.01 (s, 2H, NH ), 5.31 (s, 1H, NH), 7.39
2
(
m, 4H, ArH), 8.10-8.17 (m, 4H, ArH), 8.77 (d, 1H, J = 15.6,
+
+
(s, 1H, NH). MS m/z: 405 [M ]. Anal. calcd. (%) for
HC=C) 12.43 (s, 1H, OH). MS m/z: 467 [M ]. Anal. calcd.
S: C, 61.66; H, 4.53; N, 3.0; found (%): C,
1.63; H, 4.59; N, 3.09.
-[4,5-Dimethoxy-2-(3-oxo-3-phenylprop-1-en-1-yl)-
phenylsulfonamido]benzoic acid (6d): Dark grey crystals,
(
%) for C24
H21NO
7
18 19 3 6
C H N O S: C, 53.32; H, 4.72; N, 10.36; found (%): C, 53.35;
6
H, 4.71; N, 10.34.
4,5-Dimethoxy-N'-benzoyl-2-(3-oxo-3-phenylprop-1-
en-1-yl)benzenesulfonohydrazide (6j): Light brown crystal-
3
-1
-1
line solid, m.p. 220 ºC. IR (KBr, νmax, cm ): 1419.42, 1651.52,
m.p. 201-203 ºC. IR (KBr, νmax, cm ): 1442, 1622, 3509, 3572.
1
1
3531.89. H NMR (DMSO-d
H NMR (DMSO-d
OCH ), 5.34 (s, 1H, NH), 7.43 (s, 1H,ArH), 7.49 (s, 1H,ArH),
.54 (s, 1H, ArH), 7.57 (d, J = 15.6, 1H, C=CH), 7.67-7.74
m, 5H, ArH), 8.12-8.18 (m, 3H, ArH), 8.78 (d, 1H, J = 15.6,
6
) δ: 3.78 (s, 3H, OCH
3
), 3.87 (s, 3H,
6
3
) δ: 3.79 (s, 3H, OCH ), 3.88 (s,
3
3H, OCH
3
), 5.33 (s, 1H, NH),7.43 (s, 1H, ArH), 7.49 (s, 1H,
7
ArH), 8.80 (d, 1H, J = 15.6, HC=C), 7.55 (m, 1H, C=CH),
8.10 (d, 2H, J = 7.2, ArH), 7.94 (d, 2H, J = 7.2, ArH), 7.26-
+
7.62 (m, 6H,ArH), 9.30 (s, 1H, NH). MS m/z: 466 [M ].Anal.
(
+
HC=C) 12.47(s, 1H, OH). MS m/z: 467 [M ]. Anal. calcd.
S: C, 61.66; H, 4.53; N, 3.0; found (%): C,
1.60; H, 4.56; N, 3.09.
-Chloro-5-(4,5-dimethoxy-2-(3-oxo-3-phenylprop-1-
en-1-yl)phenylsulfonamido)benzoic acid (6e): Light brown
(
%) for C24
H21NO
7
22 2 6
calcd. (%) for C24H N O S: C, 61.79; H, 4.75; N, 6.0; found
6
(%): C, 61.80; H, 4.72; N, 5.95.
4,5-Dimethoxy-N'-(4-nitrobenzoyl)-2-(3-oxo-3-phenyl-
prop-1-en-1-yl)benzenesulfonohydrazide (6k): Red crystal-
2
-1
-1
line solid, m.p. 193 ºC. IR (KBr, νmax, cm ): 1419.42, 1651.52,
solid, m.p. 210 ºC. IR (KBr, νmax, cm ): 1420.56, 1672.38,
3
1
570.29, 3568.10, 683.56. H NMR (DMSO-d
1
3531.89. H NMR (DMSO-d
6
) δ: 3.78 (s,
6
3
) δ: 3.78 (s, 3H, OCH ), 3.88 (s,
3
H, OCH ),3.87 (s, 3H, OCH ), 5.34 (s, 1H, NH), 7.43 (s, 1H,
3
3
3H, OCH ), 5.33 (s, 1H, NH),7.45 (s, 1H, ArH), 7.48 (d, 1H,
3
ArH), 7.49 (s, 1H, ArH), 7.55 (s, 1H, ArH), 7.59 (d, J = 15.6,
J = 15.6, C=CH), 7.50 (s, 1H, ArH), 8.80 (d, 1H, J = 15.6,
HC=C), 7.58-7.63 (m, 4H,ArH), 8.10-8.16 (m, 5H,ArH), 9.32
1
8
5
5
H, C=CH), 7.67-7.74 (m, 5H,ArH), 8.07-8.11 (m, 2H,ArH),
.72 (d, 1H, J = 15.6, HC=C), 12.49 (s, 1H, OH). MS m/z:
+
(s, 1H, NH). MS m/z: 511 [M ]. Anal. calcd. (%) for
+
+
01 [M ], 503 [M + 2]. Anal. calcd. (%) for C24
7
H20NO SCl: C,
C
24
H
21
N
3
O
8
S: C, 56.35; H, 4.14; N, 8.22; found (%): C, 56.33;
H, 4.10; N, 8.23.
N'-(2-Hydroxybenzoyl)-4,5-dimethoxy-2-(3-oxo-3-
7.43; H, 4.02; N, 2.79; found (%): C, 57.42; H,3.97; N, 2.81.
N-Hydroxy-4,5-dimethoxy-2-(3-oxo-3-phenylprop-1-
en-1-yl)benzenesulfonamide (6f): Pale yellow solid, m.p. 162
phenylprop-1-en-1-yl)benzenesulfonohydrazide (6l): White
-1
solid, m.p. 238 ºC. IR (KBr, νmax, cm ): 1441.40, 1652.08,
-1
1
ºC. IR (KBr, νmax, cm ): 1384.08, 1635.99, 3550.29. H NMR
1
3567.88, 3505.32. H NMR (DMSO-d
(
DMSO-d
6
) δ: 3.78 (s, 3H, OCH
3
), 3.83 (s, 3H, OCH
3
), 5.31
s, 1H, NH), 7.39 (s, 1H, ArH), 7.47 (s, 1H,ArH), 7.48 (d, 1H,
6
) δ: 3.83 (s, 3H, OCH
3.87 (s, 3H, OCH ), 5.36 (s, 1H, NH), 6.90 (d, 2H, J = 7.6,
3
3
),
(
J = 15.6, C=CH), 7.65-7.67 (m, 5H, ArH), 8.83 (d, 1H, J =
ArH), 6.93 (d, 2H, J = 8.4, ArH), 7.32 (s, 1H, ArH), 7.46 (s,
1H, ArH), 7.48 (d, 1H, J = 15.6, C=CH), 7.51 (s, 1H, ArH),
7.57-7.64 (m, 4H, ArH), 8.81 (d, 1H, J = 15.6, HC=C), 9.32
+
1
5.6, HC=C), 13.01 (s, 1H, OH ). MS m/z: 363 [M ]. Anal.
calcd. (%) for C17 S: C, 56.19; H, 4.72; N, 3.85; found
%): C, 56.22; H, 4.69; N, 3.86.
,5-Dimethoxy-2-(3-oxo-3-phenylprop-1-en-1-yl)-N'-
phenylbenzenesulfonohydrazide (6g): Black crystalline
H17NO
6
+
(
(s, 1H, NH), 13.03 (s, 1H, OH ). MS m/z: 482 [M ]. Anal.
4
22 2 7
calcd. (%) for C24H N O S: C, 59.74; H, 4.60; N, 5.81; found
(%): C, 59.71; H, 4.61; N, 5.83.
N'-(4-Hydroxybenzoyl)-4,5-dimethoxy-2-(3-oxo-3-
-1
solid, m.p. 190-193 ºC. IR (KBr, νmax, cm ): 1383.89, 1635.53,
3
1
544.98. H NMR (DMSO-d
6 3
) δ: 3.78 (s, 3H, OCH ), 3.88 (s,
phenylprop-1-en-yl)benzenesulfonohydrazide (6m): Grey
-1
3H, OCH ), 5.33 (s, 1H, NH),7.45 (s, 1H, ArH), 7.48 (d, 1H,
J = 15.6, C=CH), 7.51 (s, 1H, ArH), 8.80 (d, 1H, J = 15.6,
3
crystalline solid, m.p. 215 ºC. IR (KBr, νmax, cm ): 1436.64,
1
1623.26, 3534.05, 3503.81. H NMR (DMSO-d
6
) δ: 3.79 (s,
HC=C), 7.59-7.64 (m, 5H, ArH), 8.11-8.17(m, 5H,ArH), 9.32
+
s, 1H, NH). MS m/z: 438 [M ]. Anal. calcd. (%) for
3H, OCH ), 3.86 (s, 3H, OCH ), 5.35 (s, 1H, NH), 6.90 (d,
3
3
(
2H, J = 7.6, ArH), 6.93 (d, 2H, J = 8.4, ArH), 7.32 (s, 1H,
ArH), 7.46 (s, 1H, ArH), 7.48 (d, 1H, J = 15.6, C=CH), 7.51
(s, 1H, ArH), 7.53-7.64 (m, 4H, ArH), 8.81 (d, 1H, J = 15.6,
C
23
22 2 5
H N O S: C, 63.0; H, 5.06; N, 6.39; found (%): C, 63.03;
H, 5.04; N, 6.36.