Browse > Article
http://dx.doi.org/10.5012/jkcs.2013.57.5.606

Oxidative Cyclisation Based One-Pot Synthesis of 3-Substituted[1,2,4]triazolo[4,3-b]pyridazines Using Me4NBr/Oxone  

Ruso, Jayaraman Sembian (Department of Polymer Science, Maramalai Campus, University of Madras)
Nagappan, Rajendiran (Department of Polymer Science, Maramalai Campus, University of Madras)
Kumaran, Rajendran Senthil (Syngene International Ltd.)
Publication Information
Journal of the Korean Chemical Society / v.57, no.5, 2013 , pp. 606-611 More about this Journal
Abstract
A facile one-pot syhthesis of 3-substituted triazolopyridazine and thieno-triazolopyridazine derivatives is described. This protocol involves the preparation of heteroaryl hydrazone from the aldehyde and pyridazinohydrazine derivative followed by subjecting the intermediate directly to oxidative cyclization to assemble the desired 1,2,4-triazloe moiety by employing the mixture of Me4NBr and oxone. This condition is efficient and is able to tolerate wide range of functional groups.
Keywords
1,2,4-Triazolopyridazine; Tetramethylammonium bromide; Oxone; Aromatic aldehyde;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Kucukguzel, I. I.; Kucukguzel, S. G.; Rollas, S.; Kiraz, M. Bioorg. Med. Chem. Lett. 2001, 11, 1703-1707   DOI   ScienceOn
2 Ulusoy, N.; Gursoy, A.; Otuk, G. II Farmaco 2001, 56, 947-952   DOI   ScienceOn
3 Papakostantinou, S.; Garoufalias, N.; Pouli, P.; Marakos, A.; Ladas, A.C. II Farmaco 2002, 57, 973-977   DOI   ScienceOn
4 Patel, N. B.; Khan, I. H.; Rajani, S. D. Eur. J. Med. Chem. 2010, 45, 4293-4299   DOI   ScienceOn
5 Shiradkar, M.; Kumar, G. V. S.; Dasari, V.; Tatikonda, S.; Akula, K.C.; Shah, R. Eur. J. Med. Chem. 2007, 42, 807-816   DOI   ScienceOn
6 Parmar, S. S.; Gupta, G. A. K.; Singh, H. H.; Gupta, T. K. J. Med. Chem. 1972, 15, 999-1000   DOI
7 Wang, L. C.; Tu, C. H.; Wang, J. H.; Lee, G. H. Molecules 2006, 11, 169-176   DOI
8 Zitouni, G. T.; Kaplanciki, Z. A.; Ozdemir, A.; Chevallet, P.; Kandilci, H. B.; Gumusel, B. Arch. Pharm. Chem. Life. Sci. 2007, 11, 586-590
9 Sarva, M. C.; Romeo, G.; Guerrera, F.; Siracusa, M.; Alerno, L.; Russo, F.; Cagnotto, A.; Goegan, M.; Mennin, T. Cheminform. 2010, 33, 2002-2004
10 Holla, B. S.; Veerendra, B.; Poojary, M. K. Eur. J. Med. Chem. 2003, 38, 759-767   DOI   ScienceOn
11 Parmar, S. S.; Chaudhary, M.; Chaudhary, S. K.; Kumar, S.; Spiro, H. R. J. Pharm. Sci. 1977, 66, 971-975.   DOI
12 Shimizu, S.; Endo, T.; Izumi, K.; Mikamiyama, H. Org. Process Res. Dev. 2007, 11, 1055-1058   DOI   ScienceOn
13 Marino, J. P. Jr.; et al. J. Med. Chem. 2007, 50, 3777-3785.   DOI   ScienceOn
14 Bower, J. D.; Doyle, F. P. J. Chem. Soc. 1957, 727-732   DOI
15 Gibson, M. S. Tetrahedron 1963, 19, 1587-1589   DOI   ScienceOn
16 Pollak, A.; Ti-sler, M. Tetrahedron 1966, 22, 2073-2079   DOI   ScienceOn
17 El-Gazzar, A. B.; Hassan, N. A. Molecules 2000, 5, 835-850   DOI
18 Abdel-Fattah, B.; Kandeel, M. M.; Abdel-Hakeem, M.; Fahmy, Z. M. J. Chin. Chem. Soc. 2006, 53, 403-412   DOI
19 Shawali, A. S.; Hassaneen, H. M.; Shurrab, N. K. Tetrahedron 2008, 64, 10339-10558   DOI   ScienceOn
20 Shawali, A. S.; Hassaneen, H. M.; Shurrab, N. K. Heterocycles 2008, 75, 1479-1488   DOI
21 Shawali, A. S.; Gomha, S. M. Tetrahedron 2002, 58, 8559-8564   DOI   ScienceOn
22 Son. Y. H.; Son. H. Y. Bull. Korean Chem. Soc. 2010, 31, 2242-2246   DOI   ScienceOn
23 Unqureanu, M.; Mangalagiu, I.; Grosu, G.; Petrovanu, M. Ann. Pharm. Fr. 1997, 55, 69-72
24 Mogilaiah, K.; Chandra, A. V.; Srivani, N. Indian J. Chem. 2011, 50B, 1187-1191
25 Thiel, O. R.; Achmatowicz, M. M.; Reichelt, A.; Larsen, R. D. Angew. Chem. Int. Ed. 2010, 49, 8395-8398   DOI   ScienceOn
26 Staben, S.; Blaquiere, N. Angew. Chem. Int. Ed. 2010, 49, 325-328.   DOI   ScienceOn
27 Galtie, C.; Mavel, S.; Snoeck, R.; Andre, G.; Pannecouque, C.; Witvrouw, M.; Balzarini, J.; Clercq, E. D.; Gueiffier, A. Antivir. Chem. & Chemother. 2003, 14, 177-182   DOI
28 Islam, M.; Siddiqui, A. A.; Rajesh, R. Acta Pol Pharm. 2008, 65, 441-447
29 Yas sin, F. A. Chem. Heterocycl. Comp. 2009, 45, 997-1003   DOI
30 Zhou, J.; Fan, H. T.; Song, B. A.; Jin, L. H.; Bhadury, P. S.; Hu, D. Y.; Yang, S. Phosphorus. Sulfur. Silicon Relat. Elem. 2010, 186, 81-87   DOI   ScienceOn
31 Bloomer, L.C.; Wotring, L. L.; Townsend, L. B. Cancer Res. 1982, 42, 100-106
32 Katz, D. J.; Wise, D. S.; Townsend, L. B. J. Med. Chem. 1982, 25, 813-321.   DOI
33 Corina, M.; Casiraghi, G.; Zetta, L.C. J. Org. Chem. 1991, 56, 5466-5468   DOI
34 Abubshait, S. A. Molecules 2007, 12, 25-42   DOI
35 Yokoyama, M.; Tanabe, T.; Toyoshima, A.; Togo, H. Chem Lett. 1994, 517, 265-268
36 Mantu, D.; Luca, M. C.; Moldoveanu, C.; Zbancioc, G.; Mangalagiu, I. Eur. J. Med. Chem. 2010, 45, 5164-5168   DOI   ScienceOn
37 Malinka, W.; Redizicka, A.; Lozach, O. II Farmaco 2004, 59, 457-462.   DOI   ScienceOn
38 Albright, J. D.; Moran, D. P.; Wright, W. B.; Collins, J. P.; Beer, B.; Lipa, A. S.; Greenblatt, E. N. J. Med. Chem. 1981, 24, 592-600   DOI
39 Atack, J. R. et al. J. Pharmacol Exp Ther. 2010, 332, 17-25   DOI   ScienceOn
40 Biagi, G.; Giorgi, I.; Livi, O.; Manera, C.; Scartoni, V.; Lucacchini, A.; Senatore, G. II Farmaco 1996, 51, 601-608
41 Licata, S. C.; Platt, D. M.; Ruedi-Bettschen, D. R.; Atack, J. R.; Dawson, G. R.; Van Linn, M. L.; Cook, J. M.; Rowlett, J. K. Neuropharmacology 2010, 58, 357-364.   DOI   ScienceOn
42 El-Dean, A. M. K.; Gaber, A. E. M.; El-Gaby, M. S. A.; Eyada, H. A. Cheminform. 2004, 35, 321-344
43 Singh, A. K.; Hedge, G. L.; Khanum, S. A.; Shashikanth, S. Indian J. Pharm. Sci. 2005, 67, 210-215
44 Pieretti, S.; Ominici, L. D.; Di Giannuario, A.; Cesari, N.; Dal Piaz, V. Life Sci. 2006, 79, 791-800   DOI   ScienceOn
45 Zaher, A. F. A.; Refaat, H. M.; Fawzy, O. M. Bull. Fac. Pharm. Cairo. Univ. 2009, 47, 69-75.
46 Street, L. J. et al. J. Med. Chem. 2004, 47, 3642-3657   DOI   ScienceOn
47 Shamroukh, A. H.; Ali, M. A. Arch. Pharm. 2008, 341, 223-230   DOI   ScienceOn
48 Albrecht, B. K. et al. J. Med. Chem. 2008, 51, 2879-2882.   DOI   ScienceOn