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This work is licensed under a Creative Commons Attribution 4.0 International License.
One-Pot Synthesis of Novel 3,5-Disubstituted-1,2,4-oxadiazoles from Indazole Carboxylic Acid Esters and Amidoximes
Corresponding Author(s) : Udutha Kumara Swamy
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
An efficient and high-yielding one-pot synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from indazole carboxylic acid methyl esters and amidoximes is described. In this study a series of novel 3,5-disubstituted-1,2,4-oxadiazoles (3a-d), (4a-d), (5a-d), (6a-d), (7a-d) were synthesized using amidoximes 2a-d and indazole carboxylic acid esters (3-6).
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- (a) G.D. Diana, D.L. Volkots, T.J. Nitz, T.R. Bailey, M.A. Long, N. Vescio, S. Aldous, D.C. Pevear and F.J. Dutko, J. Med. Chem., 37, 2421 (1994); doi:10.1021/jm00041a022.; (b) S. Borg, R.C. Vollinga, M. Labarre, K. Payza, L. Terenius and K. Luthman, J. Med. Chem., 42, 4331 (1999); doi:10.1021/jm990197+.
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References
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H.Z. Zhang, S. Kasibhatla, J. Kuemmerle, W. Kemnitzer, K. Ollis-Mason, L. Qiu, C. Crogan-Grundy, B. Tseng, J. Drewe and S.X. Cai, J. Med. Chem., 48, 5215 (2005); doi:10.1021/jm050292k.
Z. Li, W. Chen, J.J. Hale, C.L. Lynch, S.G. Mills, R. Hajdu, C.A. Keohane, M.J. Rosenbach, J.A. Milligan, G.J. Shei, G. Chrebet, S.A. Parent, J. Bergstrom, D. Card, M. Forrest, E.J. Quackenbush, L.A. Wickham, H. Vargas, R.M. Evans, H. Rosen and S. Mandala, J. Med. Chem., 48, 6169 (2005); doi:10.1021/jm0503244.
J. Roppe, N.D. Smith, D. Huang, L. Tehrani, B. Wang, J. Anderson, J. Brodkin, J. Chung, X. Jiang, C. King, B. Munoz, M.A. Varney, P. Prasit and N.D.P. Cosford, J. Med. Chem., 47, 4645 (2004); doi:10.1021/jm049828c.
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C.J. Swain, R. Baker, C. Kneen, J. Moseley, J. Saunders, E.M. Seward, G. Stevenson, M. Beer, J. Stanton and K. Watling, J. Med. Chem., 34, 140 (1991); doi:10.1021/jm00105a021.
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F.I. Carroll, J.L. Gray, P. Abraham, M.A. Kuzemko, A.H. Lewin, J.W. Boja and M.J. Kuhar, J. Med. Chem., 36, 2886 (1993); doi:10.1021/jm00072a007.
S. Borg, G. Estenne-Bouhtou, K. Luthman, I. Csoeregh, W. Hesselink and U. Hacksell, J. Org. Chem., 60, 3112 (1995); doi:10.1021/jo00115a029.
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P.L. Durette, W.K. Hagmann, I.E. Kopka and M. MacCoss, WO 00/71572 A1 (2000).
D.M. Cottrell, J. Capers, M.M. Salem, K. DeLuca-Fradley, S.L. Croft and K.A. Werbovetz, Bioorg. Med. Chem., 12, 2815 (2004); doi:10.1016/j.bmc.2004.03.054.
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D.N. Nicolaides, K.C. Fylaktakidou, K.E. Litinas and D. Hadjipavlou-Litina, Eur. J. Med. Chem., 33, 715 (1998); doi:10.1016/S0223-5234(98)80030-5.
S. Cesarini, N. Colombo, M. Pulici, E.R. Felder and W. Brill, Tetrahedron, 62, 10223 (2006); doi:10.1016/j.tet.2006.08.016.
C.O. Kangani, D.E. Kelley and B. Day, Tetrahedron Lett., 47, 6497 (2006); doi:10.1016/j.tetlet.2006.07.032.
V. Polshettiwar and R.S. Varma, Tetrahedron Lett., 49, 879 (2008); doi:10.1016/j.tetlet.2007.11.165.
H.A. Rajapakse, H. Zhu, M.B. Young and B.T. Mott, Tetrahedron Lett., 47, 4827 (2006); doi:10.1016/j.tetlet.2006.05.051.
G. Navarrete-Vázquez, G.M´. Molina-Salinas, Z.V. Duarte-Fajardo, J. Vargas-Villarreal, S. Estrada-Soto, F. González-Salazar, E. Hernández-Núñez and S. Said-Fernández, Bioorg. Med. Chem., 15, 5502 (2007); doi:10.1016/j.bmc.2007.05.053.
M. Ankersen, B. Peschke, B.S. Hansen and T.K. Hansen, Bioorg. Med. Chem. Lett., 7, 1293 (1997); doi:10.1016/S0960-894X(97)00216-3.
C.B. Vu, E.G. Corpuz, T.J. Merry, S.G. Pradeepan, C. Bartlett, R.S. Bohacek, M.C. Botfield, C.J. Eyermann, B.A. Lynch, I.A. MacNeil, M.K. Ram, M.R. van Schravendijk, S. Violette and T.K. Sawyer, J. Med. Chem., 42, 4088 (1999); doi:10.1021/jm990229t.
J. Matsumoto, T. Takahashi, M. Agata, H. Toyofuku and N. Sasada, Jpn. J. Pharmacol., 65, 51 (1994); doi:10.1254/jjp.65.51.
K. Ohmoto, T. Yamamoto, T. Horiuchi, H. Imanishi, Y. Odagaki, K. Kawabata, T. Sekioka, Y. Hirota, S. Matsuoka, H. Nakai, M. Toda, J.C. Cheronis, L.W. Spruce, A. Gyorkos and M. Wieczorek, J. Med. Chem., 43, 4927 (2000); doi:10.1021/jm0004087.
J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen and F.-U. Geschke, J. Med. Chem., 44, 619 (2001); doi:10.1021/jm0010623.
S. Chiou and H.J. Shine, J. Heterocycl. Chem., 26, 125 (1989); doi:10.1002/jhet.5570260122.
A.R. Gangloff, J. Litvak, E.J. Shelton, D. Sperandio, V.R. Wang and K.D. Rice, Tetrahedron Lett., 42, 1441 (2001); doi:10.1016/S0040-4039(00)02288-7.
(a) T.L. Deegan, T.J. Nitz, D. Cebzanov, D.E. Pufko and J.A. Porco Jr., Bioorg. Med. Chem. Lett., 9, 209 (1999); doi:10.1016/S0960-894X(98)00712-4.; (b) R.F. Poulain, A.L. Tartar and B.P. Deprez, Tetrahedron Lett., 42, 1495 (2001); doi:10.1016/S0040-4039(00)02293-0.
C.D. Bedford, R.A. Howd, O.D. Dailey, A. Miller, H.W. Nolen, R.A. Kenley, J.R. Kern and J.S. Winterle, J. Med. Chem., 29, 2174 (1986); doi:10.1021/jm00161a008.
(a) K. Rice and J.M. Nuss, Bioorg. Med. Chem. Lett., 11, 753 (2001); doi:10.1016/S0960-894X(01)00028-2.; (b) A.R. Gangloff, J. Litvak, E.J. Shelton, D. Sperandio, V.R. Wang and K.D. Rice, Tetrahedron Lett., 42, 1441 (2001); doi:10.1016/S0040-4039(00)02288-7.
(a) Y. Wang, R.L. Miller, D.R. Sauer and S.W. Djuric, Org. Lett., 7, 925 (2005); doi:10.1021/ol050007r.; (b) M. Adib, A.H. Jahromi, N. Tavoosi, M. Mahdavi and H.R. Bijanzadeh, Tetrahedron Lett., 47, 2965 (2006); doi:10.1016/j.tetlet.2006.02.102.