May 2009
A Facile Synthesis of Furo[3,4-e]pyrazolo[3,4-b]pyridine-5(7H)-one Derivatives
via Three-Component Reaction in Ionic Liquid without Any Catalyst
473
943, 850, 813, 796, 759 cmꢁ1
;
1H NMR (DMSO-d6): d 2.23
128.63, 131.88, 134.65, 134.73, 143.71, 150.39, 153.01,
153.34, 155.29, 157.96, 172.81, 173.03. HRMS [Found: m/z
401.1386 (Mþ); Calcd for C23H19N3O4: M 401.1376].
(s, 3H, CH3), 3.04 (s, 6H, (CH3)2N), 5.43 (s, 2H, CH2), 6.86
(d, J ¼ 8.4 Hz, 2H, ArH), 7.37–7.45 (m, 3H, ArH), 7.60 (t, J
¼ 7.6 Hz, 2H, ArH), 8.20 (d, J ¼ 8.0 Hz, 2H, ArH); 13C
NMR (DMSO-d6): d 16.31, 69.25, 110.81, 111.29, 116.57,
118.08, 121.78, 121.82, 127.12, 129.94, 132.13, 132.18,
139.05, 145.72, 149.45, 151.78, 153.34, 168.39, 168.65.
HRMS [Found: m/z 384.1585 (Mþ); Calcd for C23H20N4O2: M
384.15 86].
4-(2-Chloro-5-nitrophenyl)-3-methyl-1-phenyl-1H-furo[3,4-
e]pyrazolo[3,4-b]pyridine-5(7H)-one (4l). This compound was
obtained as solid with mp 253–255ꢀC; IR (potassium bro-
mide): 3081, 1771, 1587, 1568, 1527, 1507, 1459, 1437, 1422,
1370, 1338, 1325, 1214, 1152, 1124, 1108, 1082, 1054, 1025,
947, 867, 853, 820, 757, 709 cmꢁ1 1H NMR (DMSO-d6): d
;
3-Methyl-4-(3-nitrophenyl)-1-phenyl-1H-furo[3,4-e]pyrazolo
[3,4-b]pyridine-5(7H)-one (4h). This compound was obtained
as solid with mp 259–261ꢀC; IR (potassium bromide): 3069,
2934, 1773, 1589, 1535, 1516, 1491, 1460, 1439, 1387, 1345,
1315, 1212, 1156, 1125, 1073, 1048, 1029, 875, 800, 755,
2.13 (s, 3H, CH3), 5.54 (d, J ¼ 16.0 Hz, 1H, CH), 5.64 (d, J
¼ 16.0 Hz, 1H, CH), 7.44 (t, J ¼ 7.6 Hz, 1H, ArH), 7.64 (t, J
¼ 7.6 Hz, 2H, ArH), 7.96 (s, 1H, ArH), 8.01 (d, J ¼ 8.8 Hz,
1H, ArH), 8.21 (d, J ¼ 8.0 Hz, 2H, ArH), 8.45 (d, J ¼ 8.8
Hz, 1H, ArH). HRMS [Found: m/z 420.0621 (Mþ); Calcd for
C21H1335ClN4O4: M 420.0625].
1
738, 713, 702, 692 cmꢁ1; H NMR (DMSO-d6): d 2.12 (s, 3H,
CH3), 5.53 (s, 2H, CH2), 7.42 (t, J ¼ 7.6 Hz, 1H, ArH), 7.62
(t, J ¼ 7.6 Hz, 2H, ArH), 7.90 (t, J ¼ 8.0 Hz, 1H, ArH), 8.10
(d, J ¼ 7.6 Hz, 1H, ArH), 8.20 (d, J ¼ 8.0 Hz, 2H, ArH),
8.47 (d, J ¼ 8.8 Hz, 1H, ArH), 8.51 (s, 1H, ArH); 13C NMR
(DMSO-d6): d 14.34, 68.57, 108.77, 110.48, 115.22, 120.58,
123.76, 126.07, 128.73, 132.23, 135.37, 135.39, 137.58,
143.49, 143.99, 146.68, 151.99, 166.68, 167.10. HRMS
3-Methyl-4-(3,4-methylinenedioxophenyl)-1-phenyl-1H-furo[3,
4-e]pyrazolo[3,4-b]pyridine-5(7H)-one (4m). This compound
was obtained as solid with mp 248–249ꢀC; IR (potassium bro-
mide): 3070, 2903, 1764, 1577, 1508, 1490, 1445, 1387, 1364,
1341, 1313, 1240, 1207, 1166, 1119, 1071, 1051, 1031, 924,
796, 758 cmꢁ1 1H NMR (DMSO-d6): d 2.19 (s, 3H, CH3),
;
5.47 (s, 2H, CH2), 6.18 (s, 2H, OCH2O), 7.04 (d, J ¼ 8.0 Hz,
1H, ArH), 7.12 (d, J ¼ 8.0 Hz, 1H, ArH), 7.18 (s, 1H, ArH),
7.40 (t, J ¼ 7.6 Hz, 1H, ArH), 7.61 (t, J ¼ 7.6 Hz, 2H, ArH),
8.19 (d, J ¼ 8.0 Hz, 2H, ArH); 13C NMR (DMSO-d6): d
15.67, 69.45, 102.22, 108.51, 110.70, 111.51, 116.80, 121.71,
124.38, 125.22, 127.15, 129.92, 138.93, 145.56, 147.48,
147.82, 149.03, 153.19, 168.02, 168.27. HRMS [Found: m/z
385.1065 (Mþ); Calcd for C22H15N3O4: M 385.1063].
[Found: m/z 386.1031 (Mþ); Calcd for C21H14N4O4:
M
386.1015].
4-(2,4-Dichlorophenyl)-3-methyl-1-phenyl-1H-furo[3,4-e]pyr-
azolo [3,4-b]pyridine-5(7H)-one (4i). This compound was
obtained as solid with mp 206–208ꢀC; IR (potassium bro-
mide): 3064, 2930, 1762, 1585, 1506, 1490, 1475, 1441, 1470,
1389, 1376, 1361, 1316, 1274, 1210, 1180, 1150, 1127, 1100,
1078, 1050, 1024, 893, 853, 821, 801, 757, 689 cmꢁ1
;
1H
3-Methyl-4-(thiophen-2-yl)-1-phenyl-1H-furo[3,4-e]pyrazolo[3,
4-b]pyridine-5(7H)-one (4n). This compound was obtained as
solid with mp 248–250ꢀC; IR (potassium bromide): 3098,
1761, 1579, 1541, 1515, 1490, 1438, 1384, 1360, 1340, 1311,
1266, 1225, 1201, 1181, 1131, 1116, 1076, 1050, 1028, 852,
NMR (DMSO-d6): d 2.10 (s, 3H, CH3), 5.54 (d, J ¼ 16.0 Hz,
1H, CH), 5.61 (d, J ¼ 16.0 Hz, 1H, CH), 7.43 (t, J ¼ 7.6 Hz,
1H, ArH), 7.60–7.65 (m, 3H, ArH), 7.68 (d, J ¼ 8.4 Hz, 1H,
ArH), 7.95 (s, 1H, ArH), 8.19 (d, J ¼ 8.4 Hz, 2H, ArH).
HRMS [Found: m/z 409.0385 (Mþ); Calcd for
C21H1335Cl2N3O2: M 409.0385].
817, 794, 762, 732, 716, 720 cmꢁ1 1H NMR (DMSO-d6): d
;
2.25 (s, 3H, CH3), 5.48 (s, 2H, CH2), 7.32 (t, J ¼ 8.0 Hz, 1H,
ArH), 7.40–7.46 (m, 2H, ArH), 7.61 (t, J ¼ 8.0 Hz, 2H, ArH),
7.97 (d, J ¼ 5.2 Hz, 1H, ArH), 8.18 (d, J ¼ 8.0 Hz, 2H,
ArH); 13C NMR (DMSO-d6): d 19.95, 74.20, 117.01, 122.03,
126.62, 132.01, 132.56, 134.64, 135.02, 135.44, 136.22,
143.56, 145.58, 150.10, 157.81, 172.63, 172.70. HRMS
[Found: m/z 347.0745 (Mþ); Calcd for C19H13N3O2S: M
347.0728].
4-(3,4-Dimethylphenyl)-3-methyl-1-phenyl-1H-furo[3,4-e]pyr-
azolo[3,4-b]pyridine-5(7H)-one (4j). This compound was
obtained as solid with mp 231–233ꢀC; IR (potassium bro-
mide): 2926, 2861, 1768, 1577, 1513, 1458, 1434, 1386, 1355,
1268, 1228, 1210, 1182, 1128, 1070, 1042, 1027, 852, 818,
1
808, 798, 758, 719 cmꢁ1; H NMR (DMSO-d6): d 2.11 (s, 3H,
CH3), 2.33 (s, 3H, CH3), 2.36 (s, 3H, CH3), 5.48 (s, 2H, CH2),
7.28 (d, J ¼ 8.0 Hz, 1H, ArH), 7.32–7.35 (m, 2H, ArH), 7.41
(t, J ¼ 7.6 Hz, 1H, ArH), 7.61 (t, J ¼ 7.6 Hz, 2H, ArH), 8.20
(d, J ¼ 8.0 Hz, 2H, ArH); 13C NMR (DMSO-d6): d 15.62,
19.98, 69.47, 111.34, 116.68, 121.82, 127.18, 127.47, 129.31,
129.56, 129.95, 130.93, 136.33, 138.43, 138.97, 145.61,
148.48, 153.17, 168.11, 168.31. HRMS [Found: m/z 369.1480
(Mþ); Calcd for C23H19N3 O2: M 369.1477].
3-Methyl-4-(pyridin-3-yl)-1-phenyl-1H-furo[3,4-e]pyrazolo[3,
4-b]pyridine-5(7H)-one (4o). This compound was obtained as
solid with mp 223–225ꢀC; IR (potassium bromide): 3032, 2971,
2947, 1753, 1593, 1579, 1510, 1487, 1440, 1421, 1389, 1357,
1336, 1312, 1293, 1269, 1213, 1194, 1146, 1125, 1071, 1050,
1026, 908, 848, 813, 795, 760, 717, 701 cmꢁ1 1H NMR
;
(DMSO-d6): d 2.14 (s, 3H, CH3), 5.53 (s, 2H, CH2), 7.42 (t, J ¼
7.6 Hz, 1H, ArH), 7.60–7.65 (m, 3H, ArH), 8.08 (dd, J1 ¼ 1.5
Hz, J2 ¼ 7.6 Hz, 1H, ArH), 8.20 (d, J ¼ 8.0 Hz, 2H, ArH),
8.79 (d, J ¼ 2.0 Hz, 2H, ArH); 13C NMR (DMSO-d6): d 20.39,
74.46, 116.48, 121.39, 126.52, 128.22, 132.00, 132.72, 134.66,
142.47, 155.85, 157.87, 172.67, 173.11. HRMS [Found: m/z
342.1136 (Mþ); Calcd for C20H14N4O2: M 342.1117].
3-Methyl-4-(3,4-dimethoxyphenyl)-1-phenyl-1H-furo[3,4-e]pyr-
azolo[3,4-b]pyridine-5(7H)-one (4k). This compound was
obtained as solid with mp 203–205ꢀC; IR (potassium bro-
mide): 3059, 3018, 2930, 1768, 1589, 1570, 1512, 1460, 1438,
1412, 1355, 1325, 1309, 1259, 1234, 1203, 1174, 1130, 1070,
1
1045, 1027, 843, 795, 761, 701 cmꢁ1; H NMR (DMSO-d6): d
2.19 (s, 3H, CH3), 3.79 (s, 3H, CH3O), 3.88 (s, 3H, CH3O),
5.47 (s, 2H, CH2), 7.10–7.17 (m, 2H, ArH), 7.20 (s, 1H, ArH),
7.41 (t, J ¼ 7.6 Hz, 1H, ArH), 7.61 (t, J ¼ 7.6 Hz, 2H, ArH),
8.19 (d, J ¼ 8.0 Hz, 2H, ArH); 13C NMR (DMSO-d6): d
20.44, 60.97, 74.11, 116.36, 119.99, 121.51, 126.54, 127.86,
3-Methyl-4-(pyridin-4-yl)-1-phenyl-1H-furo[3,4-e]pyrazolo[3,
4-b]pyridine-5(7H)-one (4p). This compound was obtained as
solid with mp 223–225ꢀC; IR (potassium bromide): 3032,
2976, 2939, 1769, 1583, 1543, 1510, 1491, 1438, 1419, 1388,
1361, 1340, 1314, 1273, 1212, 1178, 1148, 1126, 1072, 1051,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet