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Complexation of Chiral Di (N-Protected a-Amino)-b-Diketones with Some Transition Metals
Corresponding Author(s) : Ibrahim A.M. Saraireh
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
Chiral Di (N-protected a-amino)-b-diketones and its transition metal complexes have been synthesized. Di(N-protected a-amino)-b-diketones were prepared by reaction of activation of N-protected-a-amino acids (imidazolide) with a-diazoketones derived from natural amino acids in presence of lithium diisopropyl amid in tetrahydrofuran as a solvent at -78 ºC and treatment the product with rhodium acetate to remove diazo group. The synthesized compounds were characterized by analytical techniques viz: IR, NMR and elemental analysis. The thermal stability of the newly synthesized metal complexes have been studied.
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- T. Schroeder, V. Ugrinova, B. Noll and S. Brown, Dalton Trans., 1030 (2006).
- R.C. Malhotra, Pure Appl. Chem., 60, 1349 (1988).
- A. Garnovskii, B. Kharixov, L. Blanco, D. Garnovskii, A. Burlov, I. Vasilchenko and G. Bondarenko, J. Coord. Chem., 46, 365 (1999).
- B. Furniss, A. Hannaford, P. Smith and A. Tatchell, Vogel's Textbook of Practical Organic Chemistry, edn. 5 (1989).
- M.A.V.R. da Silva and L.M.N.B.F. Santos. J. Chem. Thermodyn., 38, 817 (2006).
- I. Bennett, N.J.P. Broom, R. Cassels, J.S. Elder, N.D. Masson and P.J. O'Hanlon, Bioorg. Med. Chem. Lett., 9, 1847 (1999).
- A. Dunbar, D.M. Omiatek, S.D. Thai, C.E. Kendrex, L.L. Grotzinger, W.J. Boyko, R.D. Weinstein, D.W. Skaf, C.A. Besssel, G. Denison and J.M. DeSimone, J. Ind. Eng. Chem. Res., 45, 8779 (2006).
- K. Binnemans, Chem. Rev., 107, 2592 (2007).
- (a) A.G. Myers, J.L. Gleason, T. Yoon and D.W. Kung, J. Am. Chem. Soc., 119, 656 (1997); (b) V. Pace, G. Verniest, J.V. Sinisterra, A.R. Alcántara and N. De Kimpe, J. Org. Chem., 75, 5760 (2010).
- M.Z. Ozel, M.D. Burford, A.A. Clifford, K.D. Bartle, A. Shadrin, N.G. Smart and N.D. Tinker, Anal. Chim. Acta, 346, 73 (1997).
- A. Leggio, A. Liguori, A. Procopio and G. Sindona, J. Chem. Soc. Perkin Trans. I, 1969 (1997).
- (a) V.S. Babu, H. Gopi and K. Ananda, J. Peptide Res., 53, 308, (1999); (b) B.V. Suresh and H.N. Gopi, Lett. Peptide Sci., 6, 173 (1999).
- (a) J. Podlech and D. Seebach, Angew. Chem. Int. Ed., 34, 471 (1995); (b) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstroem and U. Langel, Tetrahedron: Asymm., 6, 2245 (1995); (c) E.P. Ellmerer-Muller, D. Brossner, N. Maslouch and A. Tako, Helv. Chim. Acta, 81, 59 (1998).
- T. Ye and M.A. McKervey, Tetrahedron, 48, 8007 (1992).
- J.C. Anderson, J. Gair Ford and M. Whiting, Org. Biomol. Chem., 3, 3734 (2005).
- B.D. Harris, K.L. Bhat and M.M. Joullie, Tetrahedron, 28, 2837 (1987).
- U. Schmidt, B. Riedl, G. Haas, H. Griesser, A. Vetter and S. Weinbrenner, Synthesis, 216 (1993).
- B.F. Bonini, M. Comes-Franchini, M. Fochi, F. Laboroi, G. Mazzanti, A. Ricci and G. Varchi, J. Org. Chem., 64, 8008 (1999).
- B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, A. Ricci and G. Varchi, Polyhedron, 19, 529 (2000).
- P. Roberto, F. Renata, S. Ettore and C. Massimo, J. Chem. Soc., Perkin Trans. I, 2566 (1981).
- A.I. Vogel, A Textbook of Practical Organic Chemistry, Longmans, edn. 5, p. 432 (1996).
References
T. Schroeder, V. Ugrinova, B. Noll and S. Brown, Dalton Trans., 1030 (2006).
R.C. Malhotra, Pure Appl. Chem., 60, 1349 (1988).
A. Garnovskii, B. Kharixov, L. Blanco, D. Garnovskii, A. Burlov, I. Vasilchenko and G. Bondarenko, J. Coord. Chem., 46, 365 (1999).
B. Furniss, A. Hannaford, P. Smith and A. Tatchell, Vogel's Textbook of Practical Organic Chemistry, edn. 5 (1989).
M.A.V.R. da Silva and L.M.N.B.F. Santos. J. Chem. Thermodyn., 38, 817 (2006).
I. Bennett, N.J.P. Broom, R. Cassels, J.S. Elder, N.D. Masson and P.J. O'Hanlon, Bioorg. Med. Chem. Lett., 9, 1847 (1999).
A. Dunbar, D.M. Omiatek, S.D. Thai, C.E. Kendrex, L.L. Grotzinger, W.J. Boyko, R.D. Weinstein, D.W. Skaf, C.A. Besssel, G. Denison and J.M. DeSimone, J. Ind. Eng. Chem. Res., 45, 8779 (2006).
K. Binnemans, Chem. Rev., 107, 2592 (2007).
(a) A.G. Myers, J.L. Gleason, T. Yoon and D.W. Kung, J. Am. Chem. Soc., 119, 656 (1997); (b) V. Pace, G. Verniest, J.V. Sinisterra, A.R. Alcántara and N. De Kimpe, J. Org. Chem., 75, 5760 (2010).
M.Z. Ozel, M.D. Burford, A.A. Clifford, K.D. Bartle, A. Shadrin, N.G. Smart and N.D. Tinker, Anal. Chim. Acta, 346, 73 (1997).
A. Leggio, A. Liguori, A. Procopio and G. Sindona, J. Chem. Soc. Perkin Trans. I, 1969 (1997).
(a) V.S. Babu, H. Gopi and K. Ananda, J. Peptide Res., 53, 308, (1999); (b) B.V. Suresh and H.N. Gopi, Lett. Peptide Sci., 6, 173 (1999).
(a) J. Podlech and D. Seebach, Angew. Chem. Int. Ed., 34, 471 (1995); (b) A. Heinsoo, G. Raidaru, K. Linask, J. Jarv, M. Zetterstroem and U. Langel, Tetrahedron: Asymm., 6, 2245 (1995); (c) E.P. Ellmerer-Muller, D. Brossner, N. Maslouch and A. Tako, Helv. Chim. Acta, 81, 59 (1998).
T. Ye and M.A. McKervey, Tetrahedron, 48, 8007 (1992).
J.C. Anderson, J. Gair Ford and M. Whiting, Org. Biomol. Chem., 3, 3734 (2005).
B.D. Harris, K.L. Bhat and M.M. Joullie, Tetrahedron, 28, 2837 (1987).
U. Schmidt, B. Riedl, G. Haas, H. Griesser, A. Vetter and S. Weinbrenner, Synthesis, 216 (1993).
B.F. Bonini, M. Comes-Franchini, M. Fochi, F. Laboroi, G. Mazzanti, A. Ricci and G. Varchi, J. Org. Chem., 64, 8008 (1999).
B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, A. Ricci and G. Varchi, Polyhedron, 19, 529 (2000).
P. Roberto, F. Renata, S. Ettore and C. Massimo, J. Chem. Soc., Perkin Trans. I, 2566 (1981).
A.I. Vogel, A Textbook of Practical Organic Chemistry, Longmans, edn. 5, p. 432 (1996).