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An Efficient Two-Step Synthesis of 2,5-Disubstituted Oxazole Derivatives Involving Cu-Promoted Carbon-Carbon Single Bond Formation
Corresponding Author(s) : Suman Biswas
Asian Journal of Chemistry,
Vol. 28 No. 7 (2016): Vol 28 Issue 7
Abstract
Environment sensitive fluorescence probe to detect various organelles is emerging as an excellent tool to attract the attention of a large number of researchers around the globe. The recent developments have shown that oxazole dyes are very competent and can exhibit a useful fluorescence property in this direction. An efficient synthetic procedure towards 2,5-diaryl substituted oxazole derivatives have been reported. It is a two-step technique involving classical van Leusen protocol followed by copper-mediated coupling with aryl halides to introduce the required carbon-carbon single bond. The aryl groups are chosen in such a way so that the aryl functionalities at 2- and 5-positions of oxazole can act as acceptor and donor moiety respectively. Thus, in turn, the extended conjugation from donor moiety to acceptor moiety via the oxazole ring is set up therein. The oxazole derivatives were characterized by various spectroscopic measurements like NMR, IR and MS.
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References
P. Wipf, Chem. Rev., 95, 2115 (1995); doi:10.1021/cr00038a013.
S.C.V. Yeh, Tetrahedron, 60, 11995 (2004); doi:10.1016/j.tet.2004.10.001.
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(a) S.K. Chattopadhyay and G. Pattenden, J. Chem. Soc., Perkin Trans. 1, 15, 2429 (2000); doi:10.1039/b000751j; (b) K.C. Nicolaou, S.A. Snyder, K.B. Simonsen and A.E. Kounbis, Angew. Chem. Int. Ed. Engl., 39, 3437 (2000); (c) T. Shioiri, P. Chittari and Y. Hamada, Heterocycles, 59, 465 (2003); doi:10.3987/COM-02-S56; (d) J. Sperry and C.J. Moody, Chem. Commun., 2397 (2006); doi:10.1039/b604294e.
A.P. de Silva, H.Q.N. Gunaratne, Y. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J. Rademacher and T.E. Rice, Chem. Rev., 97, 1515 (1997); doi:10.1021/cr960386p.
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(a) J. Min, J.W. Lee, Y.H. Ahn and Y.T. Chang, J. Comb. Chem., 9, 1079 (2007); doi:10.1021/cc0700546; (b) Z. Diwu, Y. Lu, C. Zhang, D.H. Klaubert and R.P. Haugland, Photochem. Photobiol., 66, 424 (1997); doi:10.1111/j.1751-1097.1997.tb03168.x; (c) Z. Diwu, C.S. Chem, C. Zhang, D.H. Klaubert and R.P. Haugland, J. Photochem. Photobiol. A, 95, 131 (2000); doi:10.1016/S1010-6030(99)00240-3.
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R. Robinson, J. Chem. Soc., 95, 2167 (1909); doi:10.1039/ct9099502167.
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A.M. van Leusen, B.E. Hoogenboom and H. Siderius, Tetrahedron Lett., 13, 2369 (1972); doi:10.1016/S0040-4039(01)85305-3.
(a) S. Pivsa-Art, T. Satoh, Y. Kawamura, M. Miura and M. Nomura, Bull. Chem. Soc. Jpn., 71, 467 (1998); doi:10.1246/bcsj.71.467; (b) F. Bellina, C. Calandri, S. Cauteruccio and R. Rossi, Tetrahedron, 63, 1970 (2007); doi:10.1016/j.tet.2006.12.068; (c) F. Besselie‘vre, M.-B. Florence, D.S. Grierson and S. Piguel, J. Org. Chem., 73, 3279 (2008); (d) E.F. Flegeau, M.E. Popkin and M.F. Greaney, Org. Lett., 10, 2717 (2008); doi:10.1021/ol800869g; (e) S.A. Ohnmacht, P. Mamone, A.J. Culshaw and M.F. Greaney, Chem. Commun., 1241 (2008); doi:10.1039/b719466h.
(a) H.-Q. Do and O.J. Daugulis, J. Am. Chem. Soc., 129, 12404 (2007); doi:10.1021/ja075802+; (b) H.-Q. Do, R.M.K. Khan and O. Daugulis, J. Am. Chem. Soc., 130, 15185 (2008); doi:10.1021/ja805688p; (c) T. Yoshizumi, H. Tsurugi, T. Satoh and M. Miura, Tetrahedron Lett., 49, 1598 (2008); doi:10.1016/j.tetlet.2008.01.042; (d) L. Ackermann, H.K. Potukuchi, D. Landsberg and R. Vicente, Org. Lett., 10, 3081 (2008); doi:10.1021/ol801078r; (e) R.J. Phipps, M.P. Grimster and M.J. Gaunt, J. Am. Chem. Soc., 130, 8172 (2008); doi:10.1021/ja801767s; (f) I. Ban, T. Sudo, T. Taniguchi and K. Itami, Org. Lett., 10, 3607 (2008); doi:10.1021/ol8013717.
(a) F. Besselièvre, F. Mahuteau-Betzer, D.S. Grierson and S. Piguel, J. Org. Chem., 73, 3278 (2008); doi:10.1021/jo7027135; (b) C.A. Zificsak and D.J. Hlasta, Tetrahedron, 60, 8991 (2004); doi:10.1016/j.tet.2004.07.016; (c) I.V. Seregin and V. Gevorgyan, Chem. Soc. Rev., 36, 1173 (2007); doi:10.1039/b606984n; (d) D. Alberico, M.E. Scott and M. Lautens, Chem. Rev., 107, 174 (2007); doi:10.1021/cr0509760.