1432
V. S. Taile, K. M. Hatzade, and V. N. Ingle
Vol 48
56.71; H, 4.51; N, 6.96; S, 7.97; Found: C, 56.70; H, 4.50; N,
6.96; S, 7.97.
65.1. 56.4; EI-MS: 627 (M, base peak, 100), 465 (20), 310 (06),
275 (31), 244 (14), 175 (14), 145 (21), 95 (12), 78 (16); Anal.-
Calcd. for C29H29N3O9S2 (627.69): C, 55.49; H, 4.66; N, 6.69,
S, 10.22; Found: C, 55.47; H, 4.68; N, 6.70; S, 10.23.
2-(Sulfamoylphenyl)-40-(imino-4-pyridyl)-4-(2,3,4,6-tetra-O-
acetyl-400-O-b-D-glucosidoxyphenyl)-thiazole (5e) Yield 60%;
30
[a]D ¼ ꢀ16.46 (c, 0.1, DMSO); brown syrup; FTIR: 1312
2-(Sulfamoylphenyl)-40-(imino-4-fluorobenzal)-4-(400-O-b-D-
30
(SO2 str. asymmetric), 1112.4 (SO2 str. Symmetric), 1175.6
(CAOAC), 1625.2 (C¼¼N), 731.2 (CASAC), 626.8 (CAS,
glucosidoxyphenyl)-thiazole (6c) Yield 66%; [a]D ¼ ꢀ30.80
(c, 0.1, DMSO); brown syrup; FTIR: 3406.2 (AOH, broad,
stretching), 3020.1 (aromatic str.), 1642.8 (C¼¼N), 1055.1
(CAOAC), 1415.2 (SO2 asymmetric, str.), 924.8 (SO2 asym-
1
bend); H-NMR: 1.99, 2.06, 1.99, 2.05 (s, 3H) (COCH3), 4.04
(s, 1H, NH), 6.33 (d, 1H, anomeric proton), 6.82 (s, 1H, Thia-
zole), 7.10–8.25 (m, 12H, Ar-H), 8.77 (s, 1H, ACH¼¼N);
Anal. Calcd. for C35H34N4O12S2 (766.79): C, 54.82; H, 4.47;
N, 7.31; S, 8.36; Found: C, 54.80; H, 4.47; N, 7.30; S, 8.37.
2-(Sulfamoylphenyl)-40-(imino-2-furyl)-4-(2,3,4,6-tetra-O-ace-
tyl-400-O-b-D-glucosidoxyphenyl)-thiazole (5f) Yield 62%;
1
metric, str.), 630.3 (CAS, bend); H-NMR: 3.0 (1H, 50H), 3.1
(1H, 40H), 3.5 (1H, 30H), 3.3 (1H, 20H), 5.98 (dd, 1H, J1, 2
¼
8.1 Hz, 10H) anomeric proton, 6.48 (s, 1H, Thiazole), 6.52–
7.96 (m, 12H, Ar-H), 8.44 (s, 1H, ACH¼¼N); 13C-NMR: d
174.0, 163.1, 161.2, 156,3, 154.1, 146.3, 145.0, 142.3, 140.2,
133.9, 129.1, 128.4, 128.0, 127.7, 126.6, 126.3, 125.6, 124.6,
123.0, 122.9, 120.8, 118.5, 103.5, 100.1, 83.1, 76.5, 75.5, 65.7;
EI-MS: 615.6 (M, base peak, 100), 455 (28), 358 (34), 185
(22), 176 (21), 165 (12), 117 (18), 104 (12), 77 (15); Anal.-
Calcd. for C28H26FN3O8S2 (615.65): C, 54.63; H, 4.26; F,
3.06; N, 6.83, S, 10.42; Found: C, 54.64; H, 4.26; F, 3.08; N,
6.82; S, 10.43.
30
[a]D ¼ ꢀ18.77 (c, 0.1, DMSO); brown syrup; FTIR: 1322
(SO2 str. asymmetric), 1110.7 (SO2 str. Symmetric), 1177.8
(CAOAC), 1621.3 (C¼¼N), 728.6 (CASAC), 625.3 (CAS,
1
bend); H-NMR: 2.01, 1.98, 1.99, 2.06 (s, 3H) (COCH3), 3.99
(s, 1H, NH), 6.52 (d, 1H, anomeric proton), 6.70 (s, 1H, Thia-
zole), 7.02–8.30 (m, 11H, Ar-H), 8.52 (s, 1H, ACH¼¼N); Anal
Calcd. for C34H33N3O13S2 (755.77): C, 54.03; H, 4.40; N,
5.56; S, 8.49; Found: C, 54.03; H, 4.41; N, 5.55; S, 8.50.
General procedure for the preparation of 2-(sulfamoyl-
phenyl)-40-(iminoaryl/hetroaryl)-4-(400-O-b-D-glucosidoxyphenyl)-
thiazoles (6a–f). To the compound 2-(sulfamoyl phenyl)-40-
(iminoaryl/hetroaryl)-4-(2, 3, 4, 6-tetra-O-acetyl-400-O-b-D-glu-
cosidoxyphenyl)-thiazole (5a) 2 g in 25 mL of dry methanol
was added 1.5 mL of 5% CH3ONa solution. The reaction mix-
ture was kept at room temperature for additional 24 h. It was
neutralized with ion-exchanged resin (Amberlite IR-120, sd
fine, Hþ form), filtered and concentrated in vacuum to afford
viscous, strongly hygroscopic, brown colored syrupy com-
pounds. By similar way compounds (6a–f) were prepared.
2-(Sulfamoylphenyl)-40-(iminobenzal)-4-(400-O-b-D-glucosi-
2-(Sulfamoylphenyl)-40-(imino-3-indolyl)-4-(400-O-b-D-gluco-
30
sidoxyphenyl)-thiazole (6d) Yield 56%; [a]D ¼ ꢀ8.12 (c,
0.1, DMSO); brown syrup; FTIR: 3422.4 (AOH, broad,
stretching), 3028.4 (aromatic str.), 1636.2 (C¼¼N), 1058.2
(CAOAC), 1420.0 (SO2 asymmetric, str.), 920.2 (SO2 asym-
1
metric, str.), 634.1 (CAS, bend); H-NMR: 3.2 (1H, 50H), 3.0
(1H, 40H), 3.0 (1H, 30H), 3.4 (1H, 20H), 3.88 (1H, ANH, D2O
exchangeable), 6.02 (dd, 1H, J1, ¼ 8.9 Hz, 10H) anomeric
2
proton, 6.76 (s, 1H, Thiazole), 6.83–7.97 (m, 13H, Ar-H), 8.85
(s, 1H, ACH¼¼N), 9.95 (s, NH, indole); 13C-NMR: d 173.4,
161.0, 157.6, 153.2, 148.2, 143.0, 139.2, 138.4, 135.5, 130.4,
128.8, 128.6, 128.1, 127.5, 126.0, 125.2, 124.2, 123.5, 122.7,
122.4, 122.0, 120.6, 118.8, 104.2, 102.8, 100.7, 82.1, 77.4,
75.2, 65.2; EI-MS: 636.0 (M, base peak, 100), 475 (16), 357
(25), 190 (40), 170 (20), 163 (18), 117 (13), 75 (10); Anal.-
Calcd. for C30H28N4O8S2 (636.7): C, 56.59; H, 4.43; N, 8.80,
S, 10.07; Found: C, 56.62; H, 4.42; N, 8.82; S, 10.06.
30
doxyphenyl)-thiazole (6a) Yield 77%; [a]D ¼ ꢀ13.21 (c,
0.1, DMSO); brown syrup; FTIR: 3405 (AOH, broad, stretch-
ing), 2980.0 (aromatic str.), 1635.9 (C¼¼N), 1050.3 (CAOAC),
1411.5 (SO2 asymmetric, str.), 924.3 (SO2 asymmetric, str.),
1
628.4 (CAS, bend); H-NMR: 3.0 (1H, 50H), 3.1 (1H, 40H),
2-(Sulfamoylphenyl)-40-(imino-4-pyridyl)-4-(400-O-b-D-gluco-
30
3.5 (1H, 30H), 3.2 (1H, 20H), 5.85 (dd, 1H, J1, 2 ¼8.4 Hz, 10H)
anomeric proton, 7.28–8.24 (m, 13H, Ar-H), 7.70 (s, 1H, Thia-
zole), 8.60 (s, 1H,ACH¼¼N); 13C-NMR: d 175.0, 163.3,
157.5,156,0, 148.4, 145.5, 138.2, 133.6, 131.3, 129.4, 128.9,
128.6, 128.5, 127.0, 126.6, 125.6, 124.9, 122.9, 122.0, 121.0,
118.0, 105.4, 100.1, 90.6, 80.5, 76.1, 75.0, 65.4. EI-MS: 627.5
(M, 10), 434 (base peak, 100), 313 (12), 237(49), 160 (09), 91
(02); Anal.Calcd. for C28H27N3O8S (627.59): C, 55.49; H,
4.66; N, 6.69, S, 10.22; Found: C, 55.47; H, 4.66; N, 6.69; S,
10.23.
sidoxyphenyl)-thiazole (6e) Yield 65%; [a]D ¼ ꢀ11.24 (c,
0.1, DMSO); brown syrup; FTIR: 3402.6 (AOH, broad,
stretching), 3015.5 (aromatic str.), 1633.1 (C¼¼N), 1055.0
(CAOAC), 1418.0 (SO2 asymmetric, str.), 922.8 (SO2 asym-
1
metric, str.), 636.0 (CAS, bend); H-NMR: 3.0 (1H, 50H), 3.1
(1H, 40H), 3.2 (1H, 30H), 3.4 (1H, 20H), 3.92 (1H,ANH, D2O
exchangeable), 5.92 (dd, 1H, J1, ¼ 8.0 Hz, 10H) anomeric
2
proton, 6.60 (s, 1H, Thiazole), 6.72–7.82 (m, 12H, Ar-H), 7.95
(s, 1H,ACH¼¼N); 13C-NMR: d 174.5, 162.2, 157.3, 154.6,
148.0, 144.2, 138.3, 130.4, 128.2, 128.1, 127.6, 126.4, 125.3,
124.1, 121.3, 115.2, 114.5, 110.6, 103.1, 101.4, 100.8, 81.5,
77.7, 76.8, 75.5, 71.6, 65.0; EI-MS: 598.0 (M, 12), 435 (base
peak, 100 %), 330 (16), 240 (34), 162 (16), 136 (23), 77 (18);
Anal.Calcd. for C27H26N4O8S2 (598.65): C, 54.17; H, 4.38; N,
9.36, S, 10.71; Found: C, 54.16; H, 4.40; N, 9.38; S, 10.72.
2-(Sulfamoylphenyl)-40-(imino-2-furyl)-4-(400-O-b-D-glucosi-
2-(Sulfamoylphenyl)-40-(imino-4-methoxybenzal)-4-(400-O-
30
b-D-glucosidoxyphenyl)-thiazole (6b) Yield 69%; [a]D
¼
ꢀ10.24 (c, 0.1, DMSO); brown syrup; FTIR: 3484.6 (AOH,
broad, stretching), 3008.2 (aromatic str.), 1640.1 (C¼¼N),
1052.3 (CAOAC), 1414.0 (SO2 asymmetric, str.), 926.1 (SO2
1
asymmetric, str.), 631.2 (CAS, bend); H-NMR: 3.1 (1H, 50H),
30
3.3 (1H, 40H), 3.4 (1H, 30H), 3.5 (1H, 20H), 3.8 (s, 3H, OCH3),
6.11 (dd, 1H, J1, 2 ¼ 8.0 Hz, 10H) anomeric proton, 6.6 (s, 1H,
Thiazole), 6.88–8.72 (m, 12H, Ar-H), 8.8 (s, 1H, ACH¼¼N);
13C-NMR: d 173.0, 164.3, 160.5, 156.0, 153.0, 146.4, 145.3,
132.6, 131.4, 129.1, 128.4, 128.1, 127.2, 127.0, 126.7, 125.1,
124.4, 123.2, 122.4, 121.8, 119.5, 104.2, 100.5, 81.2, 76.4, 75.3,
doxyphenyl)-thiazole (6f) Yield 58%; [a]D ¼ ꢀ17.14 (c, 0.1,
DMSO); brown syrup; FTIR: 3388.8 (AOH, broad, stretching),
3081.0 (aromatic str.), 1631.0 (C¼¼N), 1055.3 (CAOAC),
1412.6 (SO2 asymmetric, str.), 932.5 (SO2 asymmetric, str.),
1
631.2 (CAS, bend); H-NMR: 3.0 (1H, 50H), 3.4 (1H, 40H),
3.2 (1H, 30H), 3.4 (1H, 20H), 6.05 (dd, 1H, J1, 2 ¼8.9 Hz, 10H)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet