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http://dx.doi.org/10.5012/bkcs.2010.31.8.2341

One Pot Synthesis of Substituted [1,2,4]-Triazolo [1',2':1,2]pyrimido [6,5-b]-quinoline and Its Antibacterial Activity  

Joshi, Ratnadeep S. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Mandhane, Priyanka G. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Chate, Asha V. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Khan, Wajid (Department of Microbiology, Maulana Azad College)
Gill, Charansingh H. (Department of Chemistry, Dr. Babasaheb Ambedkar Marathwada University)
Publication Information
Abstract
A convenient synthesis of substituted [1,2,4]-triazolo [1',2':1,2]pyrimido[6,5-b]-quinoline 4(a-i) from substituted 2-chloroquinoline-3-carbaldehyde 1(a-i) and 4H-1,2,4-triazol-3-amine 2 by using $SiO_2/K_2CO_3$ under microwave irradiation. This method affords the [1,2,4]-Triazolo [1',2':1,2]pyrimido[6,5-b]-quinoline 4(a-i) under the influence of microwave irradiation in solvent-free conditions within short span (12 - 20 min), & gaves excellent yields (89 - 95%). All the synthesized compounds were further screened for their antibacterial activities. Some of our compounds showed excellent antibacterial activities against control drugs.
Keywords
[1,2,4]-Triazolo [1',2':1,2]pyrimido[6,5-b]-quinoline; $SiO_2/K_2CO_3$; Microwave irradiation; Antibacterial activity;
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1 Jadhav, G. R.; Kale, R. P.; Shaikh, M. U.; Ghawalkar, A. R.; Nagargoje, D. R.; Shiradkar, M.; Gill. C. H. Bioorg. & Med. Chem. Letts. 2008, 16, 6244.
2 Jadhav, G. R.; Kale, R. P.; Shaikh, M. U.; Shiradkar, M.; Gill, C. H. Eur. J. Med. Chem. 2009, 44(9), 2930.   DOI
3 Joshi, R. S.; Mandhane, P. G.; Diwakar, S. D.; Gill, C. H. Ultrason. Sonochem. 2010, 17, 298.   DOI
4 Mandhane, P. G.; Joshi, R. S.; Nagargoje, D. R.; Gill, C. H. Tett. Letts. 2010, 51, 1490.   DOI
5 Kale, R. P.; Jadhav, G. R.; Shaikh, M. U.; Gill, C. H. Tett. Letts. 2009, 50, 1780.   DOI
6 Jadhav, G. R.; Kale, R. P.; Shaikh, M. U.; Gill, C. H. Chin. Chem. Letts. 2009, 20(5), 535.   DOI
7 Srivastava, A.; Singh, R. M. Ind. J. Chem. 2005, 44(B), 1868.   DOI
8 Yanborisova, O. A.; Kolla, V. I.; Vikhareva, S. A. Dep. VINTI 1990, 13, 3119.
9 Yanborisova, O, A.; Kolla, V. I.; Vikhareva, S. A. Kl him-Farm. Zh. 1991, 25(2), 24.
10 Yanborisova, O. A.; Kon'shina, T. M.; Zaks, A. S. Khim-Farm. Zh. 1996, 30(3), 52.
11 Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025.   DOI
12 Smith, K., Ed., Solid Supports and Catalysts in Organic Synthesis; Ellis Horwood and PTR Prentice Hall: New York, 1992.
13 Villemin, D.; Vlieghe, X. Sul. Letts. 1998, 21, 191.
14 Laszlo, P. Preparative Chemistry Using Supported Reagents; Academic Press: 1987.
15 Kirby, A. J.; Warren, S. G. The Organic Chemistry of Phosphorus; Elsevier: Amsterdam, 1967.
16 Dewan, S. K.; Varma, U.; Malik, S. D. J. Chem. Res. (S) 1995, 21.
17 Loupy, A.; Petit, A.; Hamelin, J.; Texier-Boulett, F.; JacKqualt, P.; Maine, D. D. Synthesis 1998, 1, 213.t: ks
18 Petrov, K. A.; Chauzov, V. A.; Erokhina. Usp. Khim. 1974, 43, 2045.
19 Atmani, A.; Combret, J. C.; Malhiac, C.; Kajima, M. J. Tett. Letts. 2000, 41, 6045.   DOI
20 Clark, J. H. Acc. Chem. Res. 2002, 35, 791.   DOI
21 Miyazaki, T.; Tokubuchi, N.; Inoue, M.; Arita, M.; Mochida, I. Energy & Fuels 1998, 12, 870.   DOI   ScienceOn
22 Diwakar, S. D.; Bhagwat, S. S.; Shingare, M. S.; Gill, C. H.; Bioorg. & Med. Chem. Letts. 2008, 18, 4678.   DOI
23 Jadhav, G. R.; Shaikh, M. U.; Shingare, M. S.; Gill, C. H. J. Het. Chem. 2008, 45(1), 1287.   DOI
24 Bringmann, G.; Reichert, Y.; Kane, V. Tetrahedron 2004, 60, 3539.   DOI
25 Ko, T. C.; Hour, M. J.; Lien, J. C.; Teng, C. M.; Lee, K. H.; Kuo, S. C.; Huang, L. J. Bioorg. & Med. Chem. Letts. 2001, 11, 279.   DOI
26 Ferrarini, P. L.; Mori, C.; Badwneh, M.; Manera, C.; Martinelli, A.; Miceli, M.; Ramagnoli, F.; Saccomanni, G. J. Hetero. Chem. 1997, 34, 1501.   DOI
27 Maguire, M. P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Zilberstein, A. J. Med. Chem. 1994, 37, 2129.   DOI
28 Bolognese, A.; Correale, G.; Manfra, M.; Sposito, A.; Novellino, E.; Lavecchi, A. J. Med. Chem. 2008, 51, 8148.   DOI
29 Gopal, M.; Shahabuddin, M. S.; Inamdar, S. R. Proc. Ind. Acad. Sci. (Chem. Sci.) 2002, 114(6), 687.   DOI
30 Baraldi, P. G.; Tabrizi, M. A.; Preti, D.; Bovero, A.; Fruttarolo, F.; Romagnoli, R.; Zaid, N. Al.; Moorman, A. R.; Varani, K.; Borea, P. A. J. Med. Chem. 2005, 48, 5001.   DOI
31 Dominguez, J.; Lobo, D. G. Eur. J. Med. Chem. 2001, 36, 555.   DOI
32 Dominguez, J.; Basante, W.; Charris, J.; Riggione, F. Farmaco 1996, 51, 407.
33 Patel, R.; Desai, K.; Chikhalia, K. J. Ind. Chem. Soc. 2003, 80, 38.
34 Birendra, N. G.; Jiban, C. S. K.; Jogendra, N. B. J. Hetero. Chem. 1984, 21, 1225.   DOI
35 Kothari, P. J.; Mehlhoff, M. A.; Singh, S. P.; Parmar, S. S.; Stenberg, V. I. J. Hetero. Chem. 17, 1369.   DOI
36 Kothari, P. J.; Singh, S. P.; Parmar S. S.; Stenberg, V. I. J. Hetero. Chem. 1980, 17, 1393.   DOI
37 Sengupta, A. K.; Misra, H. K. Ind. Chem. Soc. 1981, 8, 508.
38 Sarmah, S. C.; Bahel, S. C. J. Ind. Chem., Soc. 1982, 59, 877.
39 Roma, G.; Braccio, M. D.; Grossi, G.; Mattioli, F.; Ghia, M. Eur. J. Med. Chem. 2000, 35, 1021.   DOI
40 Chen, Y. L.; Fang, K. C.; SheuHsu, J. Y.; Tzeng, S. L. J. Med. Chem. 2001, 44, 2374.   DOI
41 Doube, D.; Blouin, M.; Brideau, M. C.; Chan, C.; Desmarais, S.; Eithier, D.; Agueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Tagari, P.; Young, R. N. Bio. & Med. Chem. Letts. 1998, 8, 1255.   DOI
42 Larsen, R. D.; Corley, E. G.; King, A. O.; Carrol, J. D.; Davis, P.; Verhoeven, T. R.; Reider, P. J.; Labelle, M.; Gauthier, J. Y.; Xiang, Y. B.; Zamboni, R. J. J. Org. Chem. 1996, 61, 3398.   DOI