Journal of the Iranian Chemical Society
(ppm)=3.80 (3HoMe, s), 6.64 (1Harom, d, J=9.6 Hz), 6.95
(1Harom, d, J = 7.6 Hz), 7.02 (2Harom, m), 7.10 (1Harom, d,
J = 9.2 Hz), 7.17 (1Harom, t, J = 8 Hz), 7.28 (1Harom, dd,
126.70, 128.13, 128.96, 129.82, 129.97, 132.19, 135.46,
137.53, 143.82, 153.99, 156.33, 159.52.
N-(4-(N-(4-methoxyphenyl)sulfamoyl)phenyl)-2-oxo-
2H-chromene-6-sulfonamide (7b1): Color = Violet;
m.p=122–125 °C; Yield=87%; Rf =0.26 (60% ethyl ace-
tate, 40% n-hexane); IR (KBr, cm−1) = 3249 (N–H), 1736
(CO), 1155, 1328 (SO2);): 1H NMR (400 MHz, DMSO-d6)
δ (ppm)=3.66 (s, 3HCH3), 6.36 (d, 1Harom, J=9.6 Hz), 6.74
(d, 2Harom, J = 8.4 Hz), 7.10 (d, 2Harom, J = 8.4 Hz), 7.30
(d, 2Harom, J = 8.8 Hz), 7.33 (d, 1Harom, J = 8.0 Hz), 7.35
J
1 = 2.4 Hz, J 2 = 2.8 Hz), 7.53 (1Harom, d, J = 8.8 Hz),
7.56 (1Harom, d, J=2.8 Hz), 7.78(1Harom, dd, J 1 =2.4 Hz,
J
2 = 2 Hz), 8.11 (1Harom, d, J = 2 Hz), 8.15 (1Harom, d,
J=9.6 Hz), 10.36 (s, 2HN-H); 13C NMR (100 MHz, DMSO-
d6) δ (ppm)=56.84, 114.43, 117.92, 118.14, 118.35, 119.09,
119.43, 123.79, 124.14, 126.78, 128.09, 129.04, 129.95,
131.08, 133.66, 135.43, 139.66, 143.86, 154.05, 156.33,
159.58.
(s, 2HN-H), 7.69 (d, 2Harom, J = 8.8 Hz), 7.89 (d, 1Harom
,
N-(3-(N-(2-methylphenyl)sulfamoyl)-4-methoxyphenyl)-2-
oxo-2H-chromene-6-sulfonamide (7a4): Color=Light Vio-
let; m.p = 126–129 °C; Yield = 88%; Rf = 0.45 (60% ethyl
acetate, 40% n-hexane); IR (KBr, cm−1)=3258 (N–H), 1733
J = 8.0 Hz), 7.97 (d, 1Harom, J = 8.0 Hz), 7.98 (s, 1Harom);
13C NMR (100 MHz, DMSO-d6) δ (ppm)=55.14, 114.40,
115.62, 118.34, 119.91, 121.20, 122.70, 128.34, 129.70,
129.72, 129.74, 130.23, 134.55, 136.40, 140.63, 142.47,
156.40, 156.69 160.92.
1
(CO), 1158, 1332 (SO2); H NMR (400 MHz, DMSO) δ
(ppm) = 2.10 (3HMe, s), 3.80 (3HoMe, s), 6.64 (1Harom, d,
J = 9.6 Hz), 6.86 (1Harom, d, J = 7.6 Hz), 6.95 (1Harom, d,
J=7.6 Hz), 7.02 (1Harom, m), 7.09 (1Harom, d, J=7.2 Hz),
N-(4-(N-(4-methylphenyl)sulfamoyl)phenyl)-2-oxo-
2H-chromene-6-sulfonamide (7b2): Color = Light Cream;
m.p = 203–205 °C; Yield = 87%; Rf = 0.66 (60% ethyl
acetate, 40% n-hexane); IR (KBr, cm−1) = 3239, 3189
(N–H), 1711 (CO), 1152, 1323 (SO2); 1H NMR (400 MHz,
7.14 (1Harom, m), 7.32 (1Harom, d, J=2.4 Hz), 7.34(1Harom
d, J = 2.4 Hz), 7.48(1Harom, d, J = 8.8 Hz), 7.71(1Harom
,
,
dd, J=2.4 Hz), 8.07 (1Harom, d, J=2 Hz), 8.14 (1Harom, d,
J = 9.6 Hz), 9.29 (s, 1HN-H), 10.23 (s, 1HN-H); 13C NMR
(100 MHz, DMSO-d6) δ (ppm) = 17.91, 56.58, 114.09,
115.64, 118.06, 118.27, 119.34, 123.66, 126.53, 126.61,
128.04, 128.66, 128.85, 128.97, 129.80, 129.95, 130.94,
134.58, 135.28, 135.47, 143.92, 154.10, 156.23, 159.61.
N-(3-(N-(4-chlorophenyl)sulfamoyl)-4-methoxyphenyl)-2-
oxo-2H-chromene-6-sulfonamide (7a5): Color=Light Vio-
let; m.p = 181–184 °C; Yield = 85%; Rf = 0.24 (60% ethyl
acetate, 40% n-hexane); IR (KBr, cm−1)=3205 (N–H), 1715
DMSO-d6) δ (ppm) = 2.16 (s, 3HCH3), 6.63 (d, 1Harom
J = 9.6 Hz), 6.88 (d, 2Harom, J = 8 Hz), 6.97 (d, 2Harom
J = 8.4 Hz), 7.22 (d, 2Harom, J = 8.8 Hz), 7.55 (d, 1Harom
J = 8 Hz), 7.58 (d, 2Harom, J = 8.8 Hz), 7.93 (dd, 1Harom
,
,
,
,
J1 = 2.4 Hz, J2 = 2.4), 8.16 (d, 1Harom, J = 9.6 Hz), 8.29
(d, 1Harom, J = 2 Hz), 10 (s, 1HN-H), 11.05 (s, 1HN-H); 13
C
NMR (100 MHz, DMSO-d6) δ (ppm) = 20.74, 118.40,
118.42, 119.06, 119.51, 121.20, 128.33, 128.84, 129.94,
129.99, 133.88, 133.91, 134.49, 134.59, 135.24, 135.33,
141.81, 143.81, 156.55, 159.53.
1
(CO), 1156, 1349 (SO2); H NMR (400 MHz, DMSO) δ
N-(4-(N-(2-methoxyphenyl)sulfamoyl)phenyl)-2-oxo-
2H-chromene-6-sulfonamide (7b3): Color = Dark Cream;
m.p = 120–122 °C; Yield= 86%; Rf = 0.23 (60% ethyl ace-
tate, 40% n-hexane); IR (KBr, cm−1) = 3247 (N–H), 1733
(CO), 1160, 1345 (SO2); 1H NMR (400 MHz, DMSO-d6) δ
(ppm) = 3.76 (s, 3HCH3), 6.36 (d, 1Harom, J = 9.6 Hz), 6.88
(d, 2Harom, J = 8.4 Hz), 7.10 (d, 2Harom, J = 8.4 Hz), 7.30
(d, 2Harom, J = 8.8 Hz), 7.33 (d, 1Harom, J = 8.0 Hz), 7.35
(ppm)=3.74 (3HoMe, s), 6.59 (1Harom, d, J=9.6 Hz), 6.94
(1Harom, d, J=9.2 Hz), 6.97 (2Harom, dd, J=8.8 Hz), 7.09
(1Harom, d), 7.13 (2Harom, dd, J=8.8 Hz), 7.47 (1Harom, d,
J = 2.4 Hz), 7.48 (1Harom, d), 7.80 (1Harom, dd, J = 2 Hz),
8.09(1Harom, d), 8.16 (1Harom, d, J = 9.6 Hz), 10.18 (s,
2HN-H); 13C NMR (100 MHz, DMSO-d6) δ (ppm)=56.75,
114.13, 117.60, 117.98, 119.13, 121.05, 123.54, 126.66,
127.72, 128.31, 129.18, 130.13, 134.17, 137.52, 138.21,
144.12, 152.21, 155.65, 159.75.
(s, 2HN-H), 7.69 (d, 2Harom, J = 8.8 Hz), 7.89 (d, 1Harom
,
J = 8.0 Hz), 7.97 (d, 1Harom, J = 8.0 Hz), 7.98 (s, 1Harom);
13C NMR (100 MHz, DMSO-d6) δ (ppm) = 55.07, 110.00,
115.69, 118.34, 119.92, 121.20, 123.84, 124.76, 125.60,
125.74, 128.36, 129.64, 130.23, 133.95, 136.40, 140.63,
142.47, 149.82, 156.99 160.92.
N-(3-(N-(4-bromophenyl)sulfamoyl)-4-methoxyphenyl)-2-
oxo-2H-chromene-6-sulfonamide (7a6): Color=Light Vio-
let; m.p = 183–185 °C; Yield = 85%; Rf = 0.24 (60% ethyl
acetate, 40% n-hexane); IR (KBr, cm−1)=3204 (N–H), 1718
1
(CO), 1156, 1349 (SO2); H NMR (400 MHz, DMSO) δ
N-(2,4-dimethylphenyl)-2-((2-oxo-2H-chromene)-6-sul-
fonamido)thiazole-4-sulfonamide (7c1): Color = Cream;
m.p = 159–161 °C; Yield = 80%; Rf = 0.5 (60% ethyl ace-
tate, 40% n-hexane); IR (KBr, cm−1) = 3256 (N–H), 1728
(ppm)=3.79 (3HoMe, s), 6.65 (1Harom, d, J=10 Hz), 6.94
(2Harom, d, J = 8 Hz), 7.07 (1Harom, d, J = 8.8 Hz), 7.24
(1Harom, d, J = 8 Hz), 7.31 (2Harom, d, J = 8.4 Hz), 7.57
(2Harom, m), 7.79(1Harom, d, J = 8.4 Hz), 8.14(1Harom, s),
8.18(1Harom, d, J = 9.6 Hz), 10.26 (s, 1HN-H), 10.38 (s,
1HN-H); 13C NMR (100 MHz, DMSO-d6) δ (ppm)=56.81,
114.37, 116.09, 118.15, 118.44, 119.43, 121.50, 124.26,
1
(CO), 1157, 1338 (SO2); H NMR (400 MHz, DMSO) δ
(ppm) = 2.01 (3HMe, s), 2.10 (3HMe, s), 6.62 (1Harom, d,
J = 9.6 Hz), 6.78 (1Harom, d, J = 8 Hz), 6.89 (1Harom, d,
J = 8.4 Hz), 6.98 (1Harom, s), 7.59 (1Harom, d, J = 8.8 Hz),
1 3