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Triazolopyrimidines: Synthesis of Aryl-1,2,4-triazolo[1,5-a]pyrimidines by Doebner-Miller Reaction and their Antibacterial Activity
Corresponding Author(s) : Mahrzadi Noureen Shahi
Asian Journal of Chemistry,
Vol. 28 No. 12 (2016): Vol 28 Issue 12
Abstract
Novel aryl-1,2,4-triazolo[1,5-a]pyrimidines (3-23) were prepared in good yields from corresponding 3-amino-1,2,4-triazoles by employing Doebner-Miller reaction. In some reactions intermediate dihydro products (3, 7, 17, 19, 23) were also isolated and identified. These compounds showed only mild antibacterial activity.
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- A.R. Katritzky, C.W. Rees and E.F.C. Scriven, Comprehensive Heterocyclic Chemistry, vol. 7, Elsevier, New York (1996).
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References
A.R. Katritzky, C.W. Rees and E.F.C. Scriven, Comprehensive Heterocyclic Chemistry, vol. 7, Elsevier, New York (1996).
G. Fischer, Adv. Heterocycl. Chem., 57, 81 (1993); doi:10.1016/S0065-2725(08)60887-9; M.A.E. Shaban and A.E.A. Morgaan, Adv. Heterocycl. Chem., 77, 345 (2000); doi:10.1016/S0065-2725(00)77009-7.
S.P. Gami, K.V. Vilapara, H.R. Khunt, J.S. Babariya and Y.T. Naliapara, Int. Lett. Chem. Phys. Astron., 30, 127 (2014); doi:10.18052/www.scipress.com/ILCPA.30.127.
B. Yu, X.-J. Shi, Y.-F. Zheng, Y. Fang, E. Zhang, D.-Q. Yu and H.-M. Liu, Eur. J. Med. Chem., 69, 323 (2013); doi:10.1016/j.ejmech.2013.08.029.
N. Zhang, S. Ayral-Kaloustian, T. Nguyen, J. Afragola, R. Hernandez, J. Lucas, J. Gibbons and C. Beyer, J. Med. Chem., 50, 319 (2007); doi:10.1021/jm060717i.
X.-L. Zhao, Y.-F. Zhao, S.-C. Guo, H.-S. Song, D. Wang and P. Gong, Molecules, 12, 1136 (2007); doi:10.3390/12051136.
H. Wang, M. Lee, Z. Peng, B. Blázquez, E. Lastochkin, M. Kumarasiri, R. Bouley, M. Chang and S. Mobashery, J. Med. Chem., 58, 4194 (2015); doi:10.1021/jm501831g.
C.M. Richardson, D.S. Williamson, M.J. Parratt, J. Borgognoni, A.D. Cansfield, P. Dokurno, G.L. Francis, R. Howes, J.D. Moore, J.B. Murray, A. Robertson, A.E. Surgenor and C.J. Torrance, Bioorg. Med. Chem. Lett., 16, 1353 (2006); doi:10.1016/j.bmcl.2005.11.048.
B.C. Gerwick, M.V. Subramanian, V.I. Loney-Gallant and D.P. Chandler, Pestic. Sci., 29, 357 (1990); doi:10.1002/ps.2780290310.
N. Parveen, S. Aslam, T. Maqbool, A.M.R. Bernadino, M.A. Munawar and M.A. Khan, Affinidad, 71, 566 (2014).
N. Perveen, M.A. Khan, M. Moazzam and M. Sarwar, J. Pure Appl. Sci. (Bahawalpur, Pakistan), 17, 39 (1998).
A. Nazeer, N. Perveen, M.A. Khan, M.N. Khan, M.A. Munawar and W. Lin, Asian J. Chem., 25, 7705 (2013); doi:10.14233/ajchem.2013.14573; A. Nazeer, N. Perveen, S. Aslam, M.A. Khan and M.A. Munawar, Affinidad, 70, 563 (2013).
W.W. Paudler and L.S. Helmick, J. Heterocycl. Chem., 3, 269 (1966); doi:10.1002/jhet.5570030306; L.M. Werbel, A. Curry, E.F. Elslager, C.A. Hess, M.P. Hutt and C. Youngstrom, J. Heterocycl. Chem., 6, 787 (1969); doi:10.1002/jhet.5570060603.
A.W. Bauer, W.M.M. Kirby, J.S. Serris and M. Turck, J. Clin. Pathol., 45, 493 (1966).