September 2009
An Efficient Method for Synthesis of Pyrano[3,2-c]pyridine Derivatives
under Microwave Irradiation
831
CH2), 3.45 (m, 3H, CH2), 3.07 (d, 1H, J ¼ 16.0 Hz, CH2),
2.69 (d, 1H, J ¼ 16.0 Hz, CH2). 13C NMR (DMSO-d6): d ¼
159.79, 143.48, 139.47, 137.74, 135.89, 128.87, 128.64,
128.38, 128.00, 127.56, 127.10, 126.91, 121.83, 120.39,
112.87, 59.89, 56.05, 52.26, 51.69, 41.07. Anal. Calcd for
C29H25N3O: C, 80.72, H, 5.84; N, 9.74; found C, 80.86; H,
5.83; N, 9.70.
CH2), 2.66 (d, 1H, J ¼ 15.6 Hz, CH2). 13C NMR (DMSO-d6):
d ¼ 159.90, 150.89, 146.73, 145.92, 142.73, 139.70, 137.52,
130.34, 130.01, 128.97, 128.57, 127.98, 126.95, 124.03,
123.60, 113.88, 59.42, 54.85, 51.58, 40.59. Anal. Calcd for
C29H23N5O5: C, 66.79; H, 4.45; N, 13.43; found C, 66.64; H,
4.47; N, 13.48.
8-(4-Bromobenzylidene)-2-amino-6-benzyl-4-(4-bromophenyl)-
5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile (5l).
IR (KBr) 3326, 3293, 2196, 1681, 1644, 1594, 1485, 1407,
1392, 1373, 1322, 1267, 1170, 1098, 1071, 1010, 917, 887,
8-(4-Chlorobenzylidene)-2-amino-6-benzyl-4-(4-chlorophenyl)-
5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile (5h).
IR (KBr) 3329, 3279, 2192, 1683, 1649, 1598, 1489, 1411,
1395, 1375, 1325, 1265, 1214, 1169, 1091, 1049, 1013, 917,
815, 749, 696 cmꢁ1 1H NMR (DMSO-d6): d 751–7.48 (m,
.
884, 826, 753, 700 cmꢁ1
.
1H NMR (DMSO-d6): d 7.43–7.39
4H, ArH), 7.14–7.12 (m, 5H, ArH), 7.10 (m, 2H, ArH) 7.02–
7.00 (m, 2H, ArH), 6.86 (brs, 2H, NH2), 6.84 (s, 1H, ¼¼CH),
3.99 (s, 1H, CH), 3.56 (d, 1H, J ¼ 14.4 Hz, CH2), 3.40–3.36
(m, 3H ,CH2), 3.00 (d, 1H, J ¼ 16.0 Hz, CH2), 2.60 (d, 1H, J
¼ 16.0 Hz, CH2). 13C NMR (DMSO-d6): d ¼ 159.77, 142.87,
139.46, 137.69, 135.06, 131.59, 131.34, 130.92, 129.83,
128.60, 128.01, 120.32, 120.23, 112.84, 59.62, 55.48, 51.75,
51.67, 40.36. Anal. Calcd for C29H23Br2N3O: C, 59.10, H,
3.94; N, 7.13; found C, 58.95; H, 3.95; N, 7.16.
(m, 4H, ArH), 7.23–7.17 (m, 7H, ArH), 7.07–7.06 (m, 2H,
ArH), 6.92 (s, 1H, ¼¼CH), 6.90 (brs, 2H, NH2), 4.07 (s, 1H,
CH), 3.61 (d, 1H, J ¼ 14.8 Hz, CH2), 3.46–3.42 (m, 3H,
CH2), 3.06 (d, 1H, J ¼ 16.8 Hz, CH2), 2.66 (d, 1H, J ¼ 16.0
Hz, CH2). 13C NMR (DMSO-d6): d ¼ 159.78, 142.45, 139.46,
137.69,134.73, 131.70, 130.62, 129.45 128.66, 128.60, 128.42,
127.99, 127.74, 126.94, 120.79, 120.19, 112.86, 112.72, 59.65,
55.60, 51.81, 51.61, 40.30. Anal. Calcd for C29H23Cl2N3O: C,
69.60, H, 4.63; N, 8.40; found C, 69.75; H, 4.62; N, 8.37.
8-(4-Fluorobenzylidene)-2-amino-6-benzyl-4-(4-fluorophenyl)-
5,6,7,8-tetrahydro-4H-pyrano[3,2-c]pyridine-3-carbonitrile (5i).
IR (KBr) 3334, 3298, 2197, 1684, 1650, 1602, 1507, 1417,
1398, 1375, 1267, 1225, 1157, 1091, 916, 831, 780, 756, 697
Acknowledgments. This work was supported by National Sci-
ence Foundation of China (No. 20672090), Natural Science
Foundation of the Jiangsu Province (No. BK20060330), the Qing
Lan Project (No. 08QLT001), and Six Kinds of Professional Elite
Foundation of Jiangsu Province (No. 06-A-039).
1
cmꢁ1. H NMR (DMSO-d6): d 7.25–7.20 (m, 4H, ArH), 7.19–
7.14 (m, 7H, ArH), 7.08–7.06 (m, 2H, ArH), 6.92 (s, 1H,
¼¼CH), 6.83 (brs, 2H, NH2), 4.05 (s, 1H, CH), 3.59 (d, 1H, J
¼ 14.0 Hz, CH2), 3.45 (s, 2H, CH2), 3.40 (d, 1H, J ¼ 14.4
Hz, CH2), 3.05 (d, 1H, J ¼ 16.0 Hz, CH2), 2.65 (d, 1H, J ¼
16.0Hz, CH2). 13C NMR (DMSO-d6): d ¼ 162.28, 159.72,
139.63, 139.37, 137.69, 132.28, 130.93, 130.85, 129.49,
129.40, 128.62, 127.99, 126.94, 120.86, 120.32, 115.51,
115.43, 115.30, 115.21, 112.66, 59.75, 55.84, 51.98, 51.57.
Anal. Calcd for C29H23F2N3O: C, 74.50; H, 4.96; N, 8.99;
found C, 74.66; H, 4.93; N, 8.95.
REFERENCES AND NOTES
[1] Dimmock, J. R.; Arora, V. K.; Duffy, M. J.; Reid, R. S.;
Allen, T. M.; Kao, G. Y. Drug Des Discov 1992, 8, 291.
[2] El-Barbary, A. A.; Khodair, A. I.; Pederson, E. B.; Nielsen,
C. J Med Chem 1994, 37, 73.
[3] Al-Obaid, A. M.; El-Subbagh, H. I.; Khodair, A. I.; El-
mazar, M. M. M. A. Anticancer Drugs 1996, 7, 873.
[4] El-Subbagh, H. I.; Abu-Zaid, S. M.; Mahran, M. A.; Badria,
F. A.; Al-Obaid, A. M. J Med Chem 2000, 43, 2915.
8-(3-Nitrobenzylidene)-2-amino-6-benzyl-5,6,7,8-tetrahydro-
4-(3-nitrophenyl)-4H-pyrano[3,2-c]pyridine-3-carbonitrile (5j).
IR (KBr) 3337, 3293, 2184, 1679, 1647, 1596, 1522, 1465,
1399, 1351, 1263, 1218, 1159, 1085, 914, 815, 739, 695, 685
[5] Hammam, A. E.-F. G.; Sharaf, M. A.; El-Hafez, N. A. A.
Indian J Chem Sect B 2001, 40B, 213.
[6] Kumar, R. R.; Perumal, S.; Senthilkumar, P.; Yogeeswari,
P.; Sriram, D. Bioorg Med Chem Lett 2007, 17, 6459.
1
cmꢁ1. H NMR (DMSO-d6): d 8.16–8.17 (m, 1H, ArH), 8.12–
[7] (a) Bose, A. K.; Banik, B. K.; Lavlinskaia, N.; Jayaraman,
M.; Manhas, M. S. Chemtech 1997, 27, 18; (b) Caddick, S. Tetrahe-
dron 1995, 51, 10403.
8.10 (m, 1H, ArH), 8.03 (brs, 2H, NH2), 7.70–7.65 (m, 4H,
ArH), 7.12–7.11 (m, 3H, ArH), 7.07 (s, 1H, ¼¼CH), 7.06–7.04
(m, 4H, ArH), 4.35 (s, 1H, CH), 3.66 (d, 1H, J ¼ 14.4 Hz,
CH2), 3.54 (d, 1H, J ¼ 15.2 Hz, CH2), 3.49–3.34 (m, 2H,
CH2), 3.13 (d, 1H, J ¼ 16.4 Hz, CH2), 2.69 (d, 1H, J ¼ 16.0
Hz, CH2). 13C NMR (DMSO-d6): d ¼ 159.78, 142.45, 139.46,
137.69, 134.73, 131.70, 130.62, 129.45, 128.66, 128.60,
128.42, 127.99, 127.74, 126.93, 120.79, 112.87, 59.65, 56.01,
55.60, 51.89, 51.81, 51.62, 40.29. Anal. Calcd for
C29H23N5O5: C, 66.79; H, 4.45; N, 13.43; found C, 66.96; H,
4.42; N, 13.39.
[8] Gedye, R.; Smith, F.; Westawaym, K.; Humera, A.; Baldi-
sern, L.; Laberge, L.; Rousell, J. Tetrahedron Lett 1986, 27, 279.
[9] (a) Soto, J. L.; Seoane, C.; Martin, N.; Blanco, L. A. Het-
erocycle 1983, 20, 803; (b) Soto, J. L.; Seoane, C.; Martin, N.; Quin-
teiro, M. Heterocycles 1984, 22, 1; (c) Popat, K. H.; Kachhadia, V.
V.; Nimavat, K. S.; Joshi, H. S. J Indian Chem Soc 2004, 81, 157; (d)
Armesto, D.; Horspool, W. M.; Martin, N.; Ramos, A.; Seoane, C. J
Chem Soc: Chem Commun 1987, 16, 1231; (e) Armesto, D.; Hors-
pool, W. M.; Martin, N.; Ramos, A.; Seoane, C. J Org Chem 1989,
54, 3069; (f) Gonzalez, R.; Martin, N.; Seoane, C.; Marco, J. L.;
Albert, A.; Cano, F. H. Tetrahedron Lett 1992, 33, 3809; (g) Martin,
N.; Seoane, C.; Soto, J. L. Tetrahedron 1988, 44, 5861; (h) Ciller, J.
A.; Martin, N.; Seoane, C.; Jose, L. S. J Chem Soc Perkin Trans 1
1985, 2581; (i) Bellanato, J.; Florencio, F.; Martin, N.; Seoane, C. J
Mol Struct 1988, 172, 63; (j) Bellanato, J.; Florencio, F.; Garcia
Blanco, S.; Martin, N.; Seoane, C. J Mol Struct 1987, 162, 19.
[10] Tu, S. J.; Jiang, B.; Zhang, Y.; Jia, R. H., Zhang, J. Y.;
Yao, C. S.; Shi, F. Org Biomol Chem 2007, 5, 355.
8-(4-Nitrobenzylidene)-2-amino-6-benzyl-5,6,7,8-tetrahydro-
4-(4-nitrophenyl)-4H-pyrano[3,2-c]pyridine-3-carbonitrile (5k).
IR (KBr) 3329, 3301, 2200, 1681, 1650, 1591, 1517, 1421,
1398, 1340, 1269, 1218, 1168, 1108, 920, 895, 859, 811, 748,
700 cmꢁ1 1H NMR (DMSO-d6): d 8.24–8.19 (m, 4H, ArH),
.
7.51–7.48 (m, 4H, ArH), 7.15 (s, 1H, ¼¼CH), 7.14–7.13 (m,
2H, ArH), 7.08–7.06 (m, 3H, ArH), 7.05 (brs 2H, NH2), 4.31
(s, 1H, CH), 3.69 (d, 1H, J ¼ 14.8 Hz, CH2), 3.53 (d, 1H, J ¼
14.8 Hz, CH2), 3.48 (s, 2H, CH2), 3.13 (d, 1H, J ¼ 16.4 Hz,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet