436 JOURNAL OF CHEMICAL RESEARCH 2015
1
3
1
1
3.95 (1HOH, s); C NMR: (CDCl ) δ (ppm) 45.5, 55.8, 92.9, 104.0,
135.9, 140.7, 141.7, 164.6, 167.4, 170.4, 170.5, 185.7. Anal. calcd for
C H NO S: C, 59.01; H, 4.01; N, 3.28; found: C, 59.23; H, 4.16; N,
3
17.7, 119.9, 120.7, 123.41, 124.0, 125.9, 129.7, 131.5, 135.5, 145.5, 156.1,
21
17
7
1
57.8, 163.6, 166.8, 180.9. Anal. calcd for C H NO S: C, 61.30; H,
3.39%.
21
17
6
4
.16; N, 3.40; found: C, 59.95; H, 3.98; N, 3.53%.
-Hydroxy-3-methoxy-9-oxo-N-phenyl-9H-xanthene-4-sulfonamide
4e): Brown solid (EtOH); m.p. 140–145 °C; R = 0.53 (80% ethyl
1-Hydroxy-3-methoxy-9-oxo-N-p-tolyl-9H-xanthene-4-sulfonamide
1
(4k): Cream solid (EtOH); m.p. 194–197 °C; R = 0.33 (70% ethyl
f
-1
(
acetate 30% n-hexane); IR: (KBr, cm ) 3456 (O–H), 3261 (N–H),
f
-1
1
acetate 20% n-hexane); IR: (KBr, cm ) 3419 (O–H), 3260 (N–H), 1661
1663 (CO), 1399, 1155(SO ); H NMR: (CDCl ) δ (ppm) 2.27 (3HMe,
2
3
1
(
6
CO), 1390, 1122 (SO ); H NMR: (CDCl ) δ (ppm) 4.13 (3HOMe, s),
s), 4.14 (3HOMe, s), 6.42 (1Harom, s), 6.64 (1Haroma, d, J = 7.6Hz), 7.01–7.05
(3Harom, m), 7.26 (1HN-H, s), 7.46 (1Harom, t, J = 7.64 Hz), 7.67 (1Harom,
2
3
.42 (1Harom, s), 7.01–7.05 (5Harom, m), 7.28 (1HN-H, s), 7.45 (1Harom, t,
J = 7.2 Hz), 7.66 (1Harom, d, J = 8.0 Hz), 7.79 (1Harom, t, J = 7.2 Hz),
d, J = 8.4 Hz), 7.81 (1Harom, t, J = 7.64 Hz), 8.24 (1Harom, d, J = 8.0
13
13
8
.23 (1Harom, d, J = 6.8 Hz), 13.89 (1HOH, s); C NMR: (CDCl ) δ
Hz), 13.90 (1HOH, s); C NMR: (CDCl ) δ (ppm) 20.7, 57.40, 94.9,
3
3
(
ppm) 55.8, 92.9, 97.1, 104.0, 117.7, 119.9, 120.7, 123.41, 124.0, 125.9,
29.7, 131.5, 135.5, 156.1, 157.8, 163.6, 166.8, 180.9. Anal. calcd for
C H NO S: C, 60.45; H, 3.80; N, 3.52; found: C, 60.23; H, 3.91; N,
103.5, 106.1, 115.3, 118.6, 119.8, 121.0, 125.0, 125.5, 129.8, 129.9,
134.2, 135.2, 135.9, 155.8, 156.3, 164.0, 167.5, 181.1. Anal. calcd for
C H NO S: C, 61.30; H, 4.16; N, 3.40; found: C, 60.18; H, 4.13; N,
1
2
0
15
6
21 17
6
3.63%.
3.36%.
N-Ethyl-1-hydroxy-3-methoxy-9-oxo-N-phenyl-9H-xanthene-
1-Hydroxy-3-methoxy-9-oxo-N-o-tolyl-9H-xanthene-4-sulfonamide
4
-sulfonamide (4f): Light brown solid (EtOH); m.p. 123–127 °C;
(4l): Cream solid (EtOH); m.p. 186–190 °C R = 0.36 (70% ethyl acetate
f
-1
-1
R = 0.433 (80% ethyl acetate 20% n-hexane); IR: (KBr, cm ) 3453
30% n-hexane); IR: (KBr, cm ) 3450 (O–H), 3300 (N–H), 1650 (CO),
f
1
1
(
1
O–H), 1662 (CO), 1397, 1176 (SO ); H NMR: (CDCl ) δ (ppm)
1379, 1175(SO ); H NMR: (DMSO-d ) δ (ppm) 2.21 (3HMe, s), 3.99
2
3
2
6
.27 (3HMe, t, J = 6.0 Hz), 3.23 (2H-CH2, q, J = 7.2 Hz), 4.13 (3HOMe, s),
(3HOMe, s), 6.99 (1Harom, s), 7.00–7.15 (4Harom, m), 7.52–7.56 (2Harom
,
6
.13 (1Harom, s), 6.98–7.03 (5Harom, m), 7.45 (1Harom, t, J = 7.2 Hz), 7.67
m), 7.88–7.93 (1Harom, m), 8.15 (1H , dd, J = 9.6 Hz, J = 4.0 Hz),
arom
1
1
13
(1Harom, d, J = 8.0 Hz), 7.79 (1Harom, t, J = 7.2 Hz), 8.22 (1Harom, d, J = 6.8
9.00 (1HN-H, s), 13.90 (1HOH, s); C NMR: (DMSO-d ) δ (ppm) 23.0,
6
13
Hz), 13.89 (1HOH, s); C NMR: (CDCl ) δ (ppm) 11.5, 40.6, 55.8, 92.9,
9
57.4, 100.7, 107.7, 113.5, 123.4, 124.5, 130.1, 130.3, 130.5, 131.0, 131.6,
135.9, 138.4, 138.8, 140.7, 141.7, 160.2, 169.8, 171.3, 185.7. Anal. calcd
for C H NO S: C, 61.30; H, 4.16; N, 3.40; found: C, 60.41; H, 4.19; N,
3
7.1, 104.0, 117.7, 119.9, 120.7, 123.41, 124.0, 125.9, 129.7, 131.5, 135.5,
156.1, 157.8, 163.6, 166.8, 180.9. Anal. calcd for C H NO S: C, 62.11;
2
2
19
6
21 17
6
H, 4.50; N, 3.29; found: C, 62.23; H, 4.37; N, 3.43%.
-Hydroxy-3-methoxy-9-oxo-N,N–diphenyl-9H-xanthene-4-
sulfonamide (4g): Brown solid (EtOH); m.p. 156–160 °C; R =0.23
3.50%.
1
N-(2,4-Dimethylphenyl)-1-hydroxy-3-methoxy-9-oxo-9H-xanthene-
4-sulfonamide (4m): Light brown solid (EtOH); m.p. 150–154 °C, R
= 0.42 (70% ethyl acetate 30% n-hexane); IR: (KBr, cm ) 3470 (O–H),
3266(N–H), 1666 (CO), 1380, 1170 (SO ); H NMR: (CDCl ) δ (ppm)
3.70 (6HCH3, s), 4.15 (3HOMe, s), 6.44 (1Harom, s), 6.73 (1Harom, d, J =
9.2 Hz), 7.07 (2Harom, d, J = 8.8 Hz), 7.18 (1HNH, s), 7.44 (1Harom, t, J =
7.6 Hz), 7.64 (1Harom, d, J = 8.4 Hz), 7.73 (1Harom, d, J = 6.8 Hz), 8.22
(1Harom, dd, J = 6.4 Hz, J = 1.2 Hz), 13.91 (1HOH, s). Anal. calcd for
f
f
-1
-1
(
(
6
80% ethyl acetate 20% n-hexane); IR: (KBr, cm ) 3393 (O–H), 1661
1
1
CO), 1403, 1178 (SO ); H NMR: (CDCl ) δ (ppm) 4.02 (3HOMe, s),
2
3
2
3
.46 (1Harom, s), 6.99–7.05 (10Harom, m), 7.44–7.47 (1Harom, m), 7.66–7.68
(
1H , m), 7.79–8.01 (1Harom, m), 8.29–8.33 (1Harom, m), 13.99 (1HOH,
arom
1
3
s); C NMR: (CDCl ) δ (ppm) 55.8, 95.1, 102.5, 106.0, 117.2, 119.1,
1
3
20.9, 123.4, 124.3, 125.9, 129.6, 131.2, 143.2, 156.6, 157.1, 162.5,
1
2
1
2
66.1, 179.9. Anal. calcd for C H NO S: C, 65.95; H, 4.04; N, 2.96; O,
C H NO S: C, 62.11; H, 4.50; N, 3.29; found: C, 62.41; H, 4.29; N,
3.20%.
N-(4-Bromophenyl)-1-hydroxy-3-methoxy-9-oxo-9H-xanthene-
2
6
19
6
22 19 6
0.27; S, 6.775; found: C, 65.63; H, 4.17; N, 3.03%.
-Hydroxy-N-(4-hydroxyphenyl)-3-methoxy-9-oxo-9H-xanthene-
-sulfonamide (4h): Cream solid (EtOH); m.p. 151–155 °C; R = 0.25
1
4
4-sulfonamide (4n): Brown solid (EtOH); m.p. 211–215 °C; R = 0.45
f
f
-1
-1
(
(
(
80% ethyl acetate 20% n-hexane); IR: (KBr, cm ) 3474 (O–H), 3289
N–H), 1656 (CO), 1400, 1148 (SO ); H NMR: (CDCl ) δ (ppm) 4.13
3HOMe, s), 4.90 (1HOH, s, br), 6.42 (1Harom, s), 6.63 (2Harom, d, J = 8.4
(70% ethyl acetate 30% n-hexane); IR (KBr, cm ) 3439 (O–H), 3272
(N–H), 1649 (CO), 1392, 1139 (SO ); H NMR: (CDCl ) δ (ppm) 4.11
(3HOMe, s), 6.50 (1Harom, s), 7.29–7.475 (4Harom, m), 7.44 (1HN-H, s), 7.51
1
1
2
3
2
3
Hz), 6.97–7.05 (3Harom,NH m), 7.45 (1Harom, t, J = 7.6 Hz), 7.67 (1Harom
d, J = 8.4 Hz), 7.81 (1Harom, t, J = 7.2 Hz), 8.23 (1Harom, d, J = 8.0 Hz),
,
(1Harom, t, J = 8.0 Hz), 7.79 (1Harom, t, J = 8.4 Hz), 7.80 (1Harom, d, J = 8.4
13
Hz), 8.30 (1Harom, t, J = 8.4 Hz), 13.07 (1HOH, s); C NMR: (CDCl3)
δ (ppm) 55.9, 95.1, 106.1,116.1, 117.6,1199, 120.7, 124.0, 125.9, 131.5,
135.7,136.6, 156.1, 157,8, 163.6, 164.3, 166.8, 180.9. Anal. calcd for
C H BrNO S: C, 50.43; H, 2.96; N, 2.94; found: C, 50.51; H, 3.09; N,
13
1
3.89 (1HOH, s); C NMR: (CDCl ) δ (ppm) 56.9, 99.2, 107.0, 117.6,
3
1
1
5
20.7, 121.3, 124.0, 125.9, 126.9, 127.8, 129.9, 131.4, 135.1, 136.0, 145.5,
56.1, 157.8, 163.7, 164.3, 167.0, 180.9. Anal. calcd for C H NO S: C,
8.11; H, 3.66; N, 3.39; found: C, 58.23; H, 3.47; N, 3.43%.
-Hydroxy-3-methoxy-N-(4-methoxyphenyl)-9-oxo-9H-xanthene-
-sulfonamide (4i): Cream solid (EtOH); m.p. 193–195 °C; R = 0.45
2
0
15
7
20 14
6
3.03%.
1
N-(4-Chlorophenyl)-1-hydroxy-3-methoxy-9-oxo-9H-xanthene-
4
4-sulfonamide (4o): Cream solid (EtOH); m.p. 237–241 °C; R = 0.34
f
f
-1
-1
(
(
(
70% ethyl acetate 30% n-hexane); IR: (KBr, cm ) 3419 (O–H), 3311
N–H), 1643 (CO), 1399, 1155 (SO ); H NMR: (CDCl ) δ (ppm) 3.71
3HOMe, s), 4.15 (3HOMe, s), 6.45 (1Harom, s), 6.79 (2Harom, d, J = 8.0 Hz),
(70% ethyl acetate 30% n-hexane); IR: (KBr, cm ) 3440 (O–H), 3209
(N–H), 1659 (CO), 1399, 1175 (SO ); H NMR: (CDCl ) δ (ppm) 4.14
1
1
2
3
2
3
(3HOMe, s), 6.43 (1Harom, s), 7.10 (2Harom, d, J = 8.8 Hz), 7.26 (1HN-H, s),
7.18–7.21 (2Harom, m), 7.48 (1Harom, t, J = 7.2 Hz), 7.67 (1Harom, d, J =
8.0 Hz), 7.83 (1Harom, t, J = 7.2 Hz), 8.26 (1Harom, d, J = 8.0 Hz), 13.95
7.08 (2Harom, d, J = 8.0 Hz), 7.07 (1HN-H, s), 7.45 (1Harom, d, J = 7.6 Hz),
7
=
.64 (1Harom, d, J = 8.4 Hz), 7.80 (1Harom, t, J = 7.6 Hz), 8.24 (1Harom, t, J
13
13
8.0 Hz), 13.92 (1HOH, s); C NMR: (CDCl ) δ (ppm) 48.4, 50.5, 88.0,
(1HOH, s); C NMR: (DMSO-d ) δ (ppm) 55.9, 95.1, 106.1, 117.6, 120.7,
3
6
107.5, 107.6, 107.7, 111.1, 112.9, 117.2, 118.6, 122.1, 129,1, 148.7, 149.3,
121.3, 124.0, 125.9, 127.9, 129.8, 135.2, 135.7, 156.1, 157,8, 163.6, 164.3,
1
3
50.8, 160.6, 174.2. Anal. calcd for C H NO S: C, 59.01; H, 4.01; N,
166.8, 180.9. Anal. calcd for C H ClNO S: C, 55.62; H, 3.27; N, 3.24;
found: C, 55.41; H, 3.39; N, 3.20%.
N-(3-Chlorophenyl)-1-hydroxy-3-methoxy-9-oxo-9H-xanthene-
21
17
7
20 14
6
.28; found: C, 59.18; H, 4.13; N, 3.36%.
-Hydroxy-3-methoxy-N-(2-methoxyphenyl)-9-oxo-9H-xanthene-
-sulfonamide (4j): Light brown solid (EtOH); m.p. 227–230 °C; R =
1
4
4-sulfonamide (4p): Cream solid (EtOH); m.p. 231–235 °C; R = 0.38
f
f
-1
-1
0.36 (70% ethyl acetate 30% n-hexane); IR: (KBr, cm ) 3443 (O–H),
(70% ethyl acetate 30% n-hexane); IR: (KBr, cm ) 3457 (O–H), 3271
(N–H), 1647 (CO), 1388, 1148(SO ); H NMR: (CDCl ) δ (ppm)
4.13(3HOMe, s), 6.47(1Harom, s), 7.03 (1Harom, t, J = 6.0 Hz), 7.15 (1Harom,
1
1
3
353 (N–H), 1650 (CO), 1402, 1161(SO ); H NMR: (DMSO-d ) δ
2
6
2
3
(
ppm) 3.57 (3HOMe, s), 3.91 (3HOMe, s), 6.65 (1Harom, s), 6.81 (1Haroma, t,
J = 8.0 Hz), 6.88 (1Haroma, d, J = 7.2 Hz ), 7.00 (1Harom, t, J = 7.6 Hz ),
.36 (1Harom , d, J = 6.4 Hz), 7.55 (1Harom, t, J = 7.6 Hz), 7.76 (1Harom
d, J = 8.4 Hz), 7.93–7.98 (1Harom, m), 8.15 (1Harom, d, J = 8.0 Hz), 9.00
t, J = 8.0 Hz), 7.21 (2Harom, d, J = 9.2 Hz), 7.38 (1HN-H, s), 7.48 (1Harom, t,
J = 7.6 Hz), 7.70 (1Harom, d, J = 8.4 Hz), 7.84 (1Harom, t, J = 8.8 Hz), 8.26
7
,
13
(1Harom, d, J = 8.0 Hz), 13.71 (1HOH, s); C NMR: (CDCl ) δ (ppm) 57.6,
3
13
(
9
1HN-H, s), 13.89 (1HOH, s); C NMR: (DMSO-d ) δ (ppm) 66.3, 66.9,
95.13, 102.9, 112.0, 117.6, 118.6, 119.9, 120.7, 123.4, 125.7, 130.3, 131.4,
135.2, 136.3, 138.8, 155.5, 155.6, 164.0, 165.1, 169.4, 180.8. Anal. calcd
6
4.7, 103.2, 110.5, 118.5, 119.2, 119.9, 121.3, 124.5, 125.0, 125.6, 126.5,