Solid Supported Peptide Catalyst for the Synthesis of Flavanone and Azaflavanones
DOI:
https://doi.org/10.12723/mjs.49.3Keywords:
Chalcones, Solid Support Peptide Catalyst, Reusable Catalyst, Cyclisation, FlavanonesAbstract
A variety of flavanones and azaflavanones have been synthesised from chalcones, catalysed by 30 mol% solid support proline terminal peptide, which is mildly efficient with high conversions yields and could be recycled up to three times without significant loss in its activity.
Keywords: , Solid Support Peptide Catalyst, Reusable Catalyst, Cyclisation, Flavanones
References
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[2] M.R.M.Andreae and A.P. Davis, Heterogeneous catalysis of the asymmetric aldol reaction by solid-supported proline-terminated peptides, Tetrahedron Asymmetry, 2005, 16(14), 2487-2492.
[3] V. Lejeune, J. Martinez and F. Cavelier, Towards a selective Bocdeprotection on acid cleavable Wang resin, Tetrahedron Letters, 2003, 44(25), 4757-4759.
[4] M. Gude, J. Ryf and P.D. White, An accurate method for the quantitation of Fmoc-derivatized solid phase supports, International Journal of Peptide Research and Therapeutics, 2002, 9(4-5), 203-206.
[5] B. A. Schutz, A. D. Wright, T. Rali and O. Sticher, Phytochemistry, 1995, 40, 12733
[6] H. Y. Chen, K. D. Dykstra, E. T. Birzin, K. Frisch, W. Chan, Y. T. Yang, R. T. Mosley, F. DiNinno, S. P. Rohrer, J. M. Schaeffer and M. L. Hammond, Bioorg Med. Chem. Lett., 2004, 14, 1417.
[7] E.S.C. Wu, I.I.I.J. Loch, B. H. Toder, A. R. Borrelli, D. Gawlak, L. A. Radow and N. P. Gensmantel, J. Med. Chem., 1992, 35, 3519.
[8] K. Higuchi, E. Umegaki, T. Watanabe, Y. Yoda, E. Morita, M. Murano and S. A. Tokioka, Journal of Gastroenterology, 2009, 44, 879.
[9] M. H. Holshouser, L. J. Loeffler and I. H. Hall, J. Med. Chem., 1981, 24, 853.
[10] P. L. Cheng, P. Fournari and J. Tirouflet, Bull. Soc. Chim. Fr., 1963, 2248.
[11] N. K. Sangawan, B. S. Varma and K. S. Dhindsa, Chem. Ind. 1984, 271.
[12] D. D. Keane, K. G. Marathe, W. I. O’Sullivan, E. M. Philbin, R. M. Simons and P. C. Teague, J. Org. Chem., 1970, 35, 2286.
[13] S. Chandrasekhar, K. Vijeender and K. V. Reddy, Tetrahedron Lett., 2005, 46, 6991.
[14] F.R. Stermitz, J.A. Adamovics and J. Geigert, Tetrahedron, 1975, 31, 1593.
[15] T. M. Harris and R. L. Carney, J. Am. Chem.Soc., 1967, 89, 6734.
[16] Z. Sanicanin and I. Tabakovic, Tetrahedron Lett., 1986, 27, 407.
[17] S.M. Ali, J. Iqbal and M. J. Ilyas, Chem. Res., 1984, (S), 236.
[18] M.R.M.Andreae and A.P. Davis, Tetrahedron Asymmetry, 2005, 16(14), 2487.
[19] J.I Lee and H.J Hung. J. Korean. Chem. Soc., 2007, (51), 106.
[20] M.J Climent, Heterocycles, 1989, 29, 115.
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2021-08-28
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