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Synthesis and Heterocyclization of 5-Amino-4-cyano-1, 3-oxazoles
Corresponding Author(s) : Mehdi Bakavoli
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
A convenient one-pot method for synthesis of some new oxazolo[5,4-d]pyrimidines via base catalyzed heterocyclization of 2-substituted 5-amino-4-cyano-1,3-oxazoles with various isothiocyanates is described.
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- a) F.A. Hassner, Heterocycles, 35, 26 (1993); b) C. Kashima, T. Maruyama and H. Arao, Rev. Heteroat. Chem., 16, 197 (1997).
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- a) M.H. Holschbach, D. Bier, S. Stüsgen, W. Wutz, W. Sihver, H.H. Coenen and R.A. Olsson, Eur. J. Med. Chem., 41, 7 (2006); b) M. Bauser, G. Delapierre, M. Hauswald, T. Flessner, D. D'Urso, A. Hermann, B. Beyreuther, J. De Vry, P. Spreyer, E. Reissmüller and H. Meier, Bioorg. Med. Chem. Lett., 14, 1997 (2004).
- a) M. Bakavoli, M. Nikpour and M. Rahimizadeh, J. Heterocycl. Chem., 43, 1327 (2006); b) M. Bakavoli, M. Rahimizadeh,A. Shiri, M. Akbarzadeh, S.H. Mousavi, H. Atapour-Mashhad and Z. Tayarani-Najaran, J. Chem. Res., 7, 403 (2010); c) M. Bakavoli, M.M. Heravi, H. Germaninajad, M. Rahimizadeh and M. Ghassemzadeh, Phosphorus Sulfur Silicon Rel. Elem., 181, 381 (2006).
- a) M.C. Carreiras,A. Eleuterio, C. Dias, M.A. Brito, D. Brites, J. MarcoContelles and E. Gomez-Sanchez, Heterocycles, 71, 2249 (2007); b) F. Freeman and D.S.H.L. Kim, Tetrahedron Lett., 30, 2631 (1989).
- a) E.J. Barreiro, C.A. Camara, H. Verli, L. Brazil-Más, N.G. Castro, W.M. Cintra, Y. Aracava, C.R. Rodrigues and C.A.M. Fraga, J. Med. Chem., 46, 1144 (2003); b) C.A. Maryanoff, Chemistry of Heterocyclic Compound: Oxazoles, (Ed. I.J. Turchi), Johan Wiley & Sons, New York, vol. 45 pp. 343-360 (1986); c) P. Camps, E. Gómez, D. Muñoz-Torrero, A. Badia, N.M. Vivas, X. Barril, M. Orozco and F.J. Luque, J. Med. Chem., 44, 4733 (2001); d) M.T. McKenna, G.R. Proctor, L.C. Young and A.L. Harvey, J. Med. Chem., 40, 3516 (1997).
References
a) F.A. Hassner, Heterocycles, 35, 26 (1993); b) C. Kashima, T. Maruyama and H. Arao, Rev. Heteroat. Chem., 16, 197 (1997).
a) G.R. Newkome and W.W. Paudler, Contemporary Heterocyclic Chemistry, Wiley, New York, vol. 1, pp. 199-231 (1982); b) M. Ogura, H. Nakayama, K. Forihata, A. Shimazu, H. Seto and N. Otake, Agric. Biol. Chem., 49, 1909 (1995).
a) Y. Tanaka, T. Kanaya, Y. Takahashi, M. Shincse, H. Tanaka and S. Omura, J. Antibiot., 46, 1208 (1993); b) M. Nakamura, H. Honma, M. Kainada, T. Ohno, S. Kunimoto and Y. Ikeda, J. Antibiot., 47, 616 (1994); c) R. Jansen, B. Kunze, H. Richenbach, B. Jurkienicz, G. Humann and G. Hofle, Liebigs Ann. Chem., 357 (1992); d) H. Takeuchi, S. Yanagida, T. Ozaki, S. Hgiwara and S. Eguchi, J. Org. Chem., 54, 431 (1989); e) R. Lakhan and R.L. Singh, J. Heterocycl. Chem., 25, 1413 (1988).
F. Freeman, T. Chen and J.B. Van Der Linden, Synthesis, 861 (1997).
a) A. Martin-Kohler, J. Widmer, G. Bold, T. Meyer, U. Séquin and P. Traxler, Helv. Chim. Acta, 87, 956 (2004); b) H.P. Dijkstra, C. Gaulon, D. Niculescu-Duvaz and C.J. Springer, Synlett., 1519 (2006).
a) M.H. Holschbach, D. Bier, S. Stüsgen, W. Wutz, W. Sihver, H.H. Coenen and R.A. Olsson, Eur. J. Med. Chem., 41, 7 (2006); b) M. Bauser, G. Delapierre, M. Hauswald, T. Flessner, D. D'Urso, A. Hermann, B. Beyreuther, J. De Vry, P. Spreyer, E. Reissmüller and H. Meier, Bioorg. Med. Chem. Lett., 14, 1997 (2004).
a) M. Bakavoli, M. Nikpour and M. Rahimizadeh, J. Heterocycl. Chem., 43, 1327 (2006); b) M. Bakavoli, M. Rahimizadeh,A. Shiri, M. Akbarzadeh, S.H. Mousavi, H. Atapour-Mashhad and Z. Tayarani-Najaran, J. Chem. Res., 7, 403 (2010); c) M. Bakavoli, M.M. Heravi, H. Germaninajad, M. Rahimizadeh and M. Ghassemzadeh, Phosphorus Sulfur Silicon Rel. Elem., 181, 381 (2006).
a) M.C. Carreiras,A. Eleuterio, C. Dias, M.A. Brito, D. Brites, J. MarcoContelles and E. Gomez-Sanchez, Heterocycles, 71, 2249 (2007); b) F. Freeman and D.S.H.L. Kim, Tetrahedron Lett., 30, 2631 (1989).
a) E.J. Barreiro, C.A. Camara, H. Verli, L. Brazil-Más, N.G. Castro, W.M. Cintra, Y. Aracava, C.R. Rodrigues and C.A.M. Fraga, J. Med. Chem., 46, 1144 (2003); b) C.A. Maryanoff, Chemistry of Heterocyclic Compound: Oxazoles, (Ed. I.J. Turchi), Johan Wiley & Sons, New York, vol. 45 pp. 343-360 (1986); c) P. Camps, E. Gómez, D. Muñoz-Torrero, A. Badia, N.M. Vivas, X. Barril, M. Orozco and F.J. Luque, J. Med. Chem., 44, 4733 (2001); d) M.T. McKenna, G.R. Proctor, L.C. Young and A.L. Harvey, J. Med. Chem., 40, 3516 (1997).