J. Khalafy, N. Etivand, A. Poursattar Marjani, and N. Khalillou
Vol 000
163.5, 162.7, 148.8, 145.5, 144.7, 142.5, 140.5, 139.8,
133.0, 130.9, 127.8, 126.5, 125.3, 124.4, 122.7, 120.4,
118.4, 115.9, 114.7, 113.2, 100.1, 56.5, 54.5 ppm; LRMS
(EI, 70 eV) m/z (%): 413 [M]+ (16), 326 (13), 297 (10),
204 (10), 193 (17), 179 (10), 193 (22), 145 (33), 120 (47),
119 (33), 105 (20), 91 (25), 78 (88), 77 (60), 69 (100), 60
(31), 57 (71), 55 (53); HRMS (ESI): m/z [M]+ calcd for
DMSO-d6) δ: 163.0, 162.4, 145.2, 142.0, 139.8, 134.2,
132.4, 131.1, 129.8, 127.8, 127.5, 124.7, 123.0, 120.9,
118.0, 116.9, 115.5, 113.9, 104.0, 100.0 ppm; LRMS
(EI, 70 eV) m/z (%): 389 [M + 2]+ (40), 387 [M]+ (100),
372 (14), 370 (47), 330 (16), 294 (12), 248 (17), 239
(20), 221 (33), 205 (33), 193 (32), 154 (23), 120 (64), 92
(43), 79 (43), 78 (99); HRMS (ESI): m/z [M]+ calcd for
C24H19N3O4: 413.1376; found: 413.1337.
4-Hydroxy-3-(2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)quinolin-
C22H14ClN3O2: 387.0775; found: 387.0721.
3-(2-(4-Bromophenyl)imidazo[1,2-a]pyridin-3-yl)-4-
2(1H)-one (4e).
White powder; yield 84%; mp: 311–
hydroxyquinolin-2(1H)-one (4h).
White powder; yield
312°C; FTIR (KBr) νmax: 3386, 3319, 3087, 2921, 2804,
87%; mp: 356–357°C; FTIR (KBr) νmax: 3306, 3160,
1
1628, 1617, 1578, 1522, 1445, 1238, 761 cmÀ1; H-NMR
3086, 2956, 2870, 1689, 1635, 1508, 1405, 1267, 1004,
1
(300 MHz, DMSO-d6) δ: 11.54 (s, 1H, exchanged by D2O
addition, OH), 7.92 (d, J = 8.7 Hz, 1H, Ar), 7.87 (d,
J = 5.7 Hz, 1H, Ar), 7.68 (d, J = 8.5 Hz, 2H, Ar), 7.62–
7.56 (m, 2H, Ar), 7.36 (d, J = 8.4 Hz, 1H, Ar), 7.35 (t,
J = 7.8 Hz, 1H, Ar), 7.21 (t, J = 6.9 Hz, 1H, Ar), 7.12 (d,
J = 8.1 Hz, 2H, Ar), 6.83 (t, J = 6.6 Hz, 1H, Ar), 2.49 (s,
3H, Me) ppm; 13C-NMR (75.5 MHz, DMSO-d6) δ: 163.1,
162.6, 151.0, 149.9, 148.8, 145.0, 143.1, 139.7, 136.9,
132.5, 130.2, 128.0, 125.9, 124.3, 122.7, 118.1, 115.7,
114.6, 113.3, 100.1, 20.4 ppm; LRMS (EI, 70 eV) m/z (%):
368 [M + 1]+ (58), 367 [M]+ (100), 350 (81), 310 (15), 248
(13), 219 (16), 183 (13), 120 (11), 78 (15); HRMS (ESI):
760 cmÀ1; H-NMR (300 MHz, DMSO-d6) δ: 11.61 (s,
1H, exchanged by D2O addition, OH), 7.93 (d, J = 8.4 Hz,
1H, Ar), 7.89 (d, J = 6 Hz, 1H, Ar), 7.73 (d, J = 8.4 Hz,
2H, Ar), 7.60–7.35 (m, 2H, Ar), 7.52 (d, J = 8.1 Hz, 2H,
Ar), 7.38 (d, J = 8.7 Hz, 1H, Ar), 7.31 (t, J = 7.8 Hz, 1H,
Ar), 7.22 (t, J = 8.1 Hz, 1H, Ar), 6.85 (t, J = 6 Hz, 1H, Ar)
ppm; 13C-NMR (75.5 MHz, DMSO-d6) δ: 162.9, 162.4,
145.2, 142.0, 139.8, 134.7, 132.9, 130.7, 130.1, 127.8,
126.6, 124.6, 122.8, 121.0, 118.1, 115.6, 113.9, 111.1,
100.0, 92.3 ppm; LRMS (EI, 70 eV) m/z (%): 279 (10),
167 (43), 149 (100), 113 (15), 85 (98), 83 (99), 71 (33), 70
(30), 57 (41); HRMS (ESI): m/z [M]+ calcd for
m/z [M]+ calcd for C23H17N3O2: 367.1321; found: 367.1355.
4-Hydroxy-3-(2-(4-hydroxy-3-methoxyphenyl)imidazo[1,2-a]
pyridin-3-yl)quinolin-2(1H)-one (4f). White powder; yield
C22H14BrN3O2: 431.0269; found: 431.0211.
4-Hydroxy-3-(2-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)
quinolin-2(1H)-one (4i). Yellow powder; yield 84%; mp:
90%; mp: 228–229°C; FTIR (KBr) νmax: 3434, 3261,
329–330°C; FTIR (KBr) νmax: 3437, 3395, 3073, 2964,
3098, 2947, 2804, 2763, 2661, 1617, 1578, 1522, 1446,
2929, 2859, 2360, 1635, 1597, 1516, 1443, 1045,
1
1
1401, 1238, 749 cmÀ1; H-NMR (300 MHz, DMSO-d6)
750 cmÀ1; H-NMR (300 MHz, DMSO-d6) δ: 11.68 (s,
δ: 11.51 (s, 1H, exchanged by D2O addition, OH), 9.02
(s, 1H, exchanged by D2O addition, OH), 7.92 (d,
J = 8.4 Hz, 2H, Ar), 7.86 (d, J = 5.7 Hz, 1H, Ar), 7.71–
7.49 (m, 2H, Ar), 7.48–7.18 (m, 4H, Ar), 6.82 (t,
J = 6.6 Hz, 1H, Ar), 6.69 (d, J = 8.4 Hz, 1H, Ar), 3.58
(s, 3H, OMe) ppm; 13C-NMR (75.5 MHz, DMSO-d6) δ:
163.6, 162.7, 147.7, 146.6, 144.6, 142.7, 139.8, 138.0,
136.4, 135.1, 130.7, 126.4, 124.4, 122.7, 120.8, 119.0,
116.6, 116.0, 114.7, 113.0, 112.1, 100.0, 58.6 ppm;
LRMS (EI, 70 eV) m/z (%): 399 [M]+ (11), 310 (10), 236
(10), 218 (16), 193 (13), 168 (11), 146 (16), 120 (51),
1H, exchanged by D2O addition, OH), 8.22 (d,
J = 8.1 Hz, 2H, Ar), 8.05 (d, J = 8.1 Hz, 2H, Ar), 7.82
(d, J = 5.1 Hz, 2H, Ar), 7.71 (d, J = 8.1 Hz, 1H, Ar),
7.62 (t, J = 8.1 Hz, 1H, Ar), 7.43–7.23 (m, 2H, Ar), 7.24
(t, J = 8.1 Hz, 1H, Ar), 6.88 (t, J = 6.6 Hz, 1H, Ar) ppm;
13C-NMR (75.5 MHz, DMSO-d6) δ: 162.9, 162.3, 146.6,
145.5, 142.0, 141.0, 140.0, 132.8, 131.2, 128.7, 127.3,
126.6, 126.3, 125.4, 125.2, 123.1, 121.0, 115.9, 115.5,
99.8 ppm; LRMS (EI, 70 eV) m/z (%): 398 [M]+ (10),
350 (10), 220 (12), 205 (29), 188 (18), 149 (33), 120
(33), 119 (58), 103 (25), 91 (43), 83 (41), 85 (95), 78
(100), 77 (89), 70 (25), 57 (92); HRMS (ESI): m/z [M]+
calcd for C22H14N4O4: 398.1015; found: 398.1099.
105 (11), 92 (34), 78 (100), 57 (27); HRMS (ESI): m/z
[M]+ calcd for C23H17N3O4: 399.1219; found: 399.1278.
3-(2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-3-yl)-4-
hydroxyquinolin-2(1H)-one (4g).
White powder; yield
88%; mp: 349–350°C; FTIR (KBr) νmax: 3215, 3092,
Acknowledgments. The authors gratefully acknowledge the
financial assistance (grant no. 96-71/DR/632) from the Urmia
University. We also thank Professor R. H. Prager of Flinders
University, Australia, for proofreading of this article.
2950, 1630, 1582, 1521, 1410, 1255, 1410, 1255, 1098,
1
844, 755 cmÀ1; H-NMR (300 MHz, DMSO-d6) δ: 11.61
(s, 1H, exchanged by D2O addition, OH), 7.93 (d,
J = 8.7 Hz, 1H, Ar), 7.89 (d, J = 7.2 Hz, 1H, Ar), 7.79
(d, J = 8.1 Hz, 2H, Ar), 7.65 (d, J = 9 Hz, 1H, Ar), 7.58
(t, J = 7.8 Hz, 1H, Ar), 7.43–7.37 (m, 3H, Ar), 7.32 (t,
J = 7.5 Hz, 1H, Ar), 7.23 (t, J = 7.8 Hz, 1H, Ar), 6.83 (t,
J = 6.3 Hz, 1H, Ar) ppm; 13C-NMR (75.5 MHz,
REFERENCES AND NOTES
[1] (a) Linton, A.; Kang, P.; Ornelas, M.; Kephart, S.; Hu, Q.;
Pairish, M.; Jiang, Y.; Guo, C. J Med Chem 2011, 54, 7705; (b) Husinec,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet