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Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

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Organocatalyzed Biomimetic Selective Reduction of C=C Double Bonds of Chalcones

https://doi.org/10.14233/ajchem.2018.21480
Vishwa Deepak Tripathi
Department of Chemistry, M.K. College, Darbhanga-846 003, India
Anand Mohan Jha
Department of Chemistry, K.S.R. College, Sarairanjan, Samastipur-848 127, India

Corresponding Author(s) : Vishwa Deepak Tripathi

vishwadeepak66@gmail.com

Asian Journal of Chemistry, Vol. 30 No. 10 (2018): Vol 30 Issue 10, 2018

Abstract

In this article, we reported a biomimetic approach for chemoselective reduction of C=C double bonds in chalcones under metal and acid free conditions, that relies on olefin activation by hydrogen bond formation. The process requires only catalytic amount of ephedrine as hydrogen bond donor and utilizes Hantzsch esters for transfer hydrogenation.

Keywords

Biomimetic Reduction Hydrogenation Hantzsch ester Chalcones
Tripathi, V. D., & Jha, A. M. (2018). Organocatalyzed Biomimetic Selective Reduction of C=C Double Bonds of Chalcones. Asian Journal of Chemistry, 30(10), 2322–2324. https://doi.org/10.14233/ajchem.2018.21480
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References
  1. M.A. Esteruelas and L.A. Oro, Chem. Rev., 98, 577 (1998); https://doi.org/10.1021/cr970322u.
  2. G. Zassinovich, G. Mestroni and S. Gladiali, Chem. Rev., 92, 1051 (1992); https://doi.org/10.1021/cr00013a015.
  3. B.C. Ranu and S. Samanta, Tetrahedron, 59, 7901 (2003); https://doi.org/10.1016/j.tet.2003.08.022.
  4. T. Suwa, E. Sugiyama, I. Shibata and A. Baba, Synlett, 556 (2000); https://doi.org/10.1055/s-2000-6585.
  5. D.B. Ramachary, M. Kishor and K. Ramakumar, Tetrahedron Lett., 47, 651 (2006); https://doi.org/10.1016/j.tetlet.2005.11.128.
  6. H. Adolfsson, Angew. Chem. Int. Ed., 44, 3340 (2005); https://doi.org/10.1002/anie.200500827.
  7. J.W. Yang, M.T. Hechavarria Fonseca, N. Vignola and B. List, Angew. Chem. Int. Ed., 44, 108 (2005); https://doi.org/10.1002/anie.200462432.
  8. S.G. Ouellet, J.B. Tuttle and D.W.C. MacMillan, J. Am. Chem. Soc., 127, 32 (2005); https://doi.org/10.1021/ja043834g.
  9. S.J. Garden, C.R.W. Guimarães, M.B. Corréa, C.A.F. Oliveira, A.C. Pinto and R. Bicca de Alencastro, J. Org. Chem., 68, 8815 (2003); https://doi.org/10.1021/jo034921e.
  10. M. Liu, P. Wilairat and M.-L. Go, J. Med. Chem., 44, 4443 (2001); https://doi.org/10.1021/jm0101747.
  11. M.L. Edwards, D.M. Stemerick and P.S. Sunkara, J. Med. Chem., 33, 1948 (1990); https://doi.org/10.1021/jm00169a021.
  12. F. Bois, C. Beney, A. Boumendjel, A.M. Mariotte, G. Conseil and A. Di Pietro, J. Med. Chem., 41, 4161 (1998); https://doi.org/10.1021/jm9810194.
  13. Y.-M. Lin, Y. Zhou, M.T. Flavin, L.-M. Zhou, W. Nie and F.-C. Chen, Bioorg. Med. Chem., 10, 2795 (2002); https://doi.org/10.1016/S0968-0896(02)00094-9.
  14. C. Furman, J. Lebeau, J.-C. Fruchart, J.-L. Bernier, P. Duriez, N. Cotelle and E. Teissier, Biochem. Mol. Toxicol., 15, 270 (2001); https://doi.org/10.1002/jbt.10003.
  15. S.F. Nielsen, S.B. Christensen, G. Cruciani, A. Kharazmi and T. Liljefors, J. Med. Chem., 41, 4819 (1998); https://doi.org/10.1021/jm980410m.
  16. S. Ducki, R. Forrest, J.A. Hadfield, A. Kendall, N.J. Lawrence, A.T. McGown and D. Rennison, Bioorg. Med. Chem. Lett., 8, 1051 (1998); https://doi.org/10.1016/S0960-894X(98)00162-0.
  17. M. Satyanarayana, P. Tiwari, B.K. Tripathi, A.K. Srivastava and R. Pratap, Bioorg. Med. Chem., 12, 883 (2004); https://doi.org/10.1016/j.bmc.2003.12.026.
  18. F. Herencia, M.L. Ferrandiz, A. Ubeda, I. Guillen, J.N. Dominguez, J.E. Charris, G.M. Lobo and M.J. Alcaraz, Free Radic. Biol. Med., 30, 43 (2001); https://doi.org/10.1016/S0891-5849(00)00443-3.
  19. J. Rojas, M. Paya, J.N. Dominguez and M. Luisa Ferrandiz, Bioorg. Med. Chem. Lett., 12, 1951 (2002); https://doi.org/10.1016/S0960-894X(02)00317-7.
  20. F. Herencia, M.L. Ferrándiz, A. Ubeda, J.N. Domínguez, J.E. Charris, G.M. Lobo and M.J. Alcaraz, Bioorg. Med. Chem. Lett., 8, 1169 (1998); https://doi.org/10.1016/S0960-894X(98)00179-6.
  21. E.B. Yang, Y.J. Guo, K. Zhang, Y.Z. Chen and P. Mack, Biochim. Biophys. Acta, 1550, 144 (2001); https://doi.org/10.1016/S0167-4838(01)00276-X.
  22. O. Prakash, A. Kumar, A. Sadana, R. Prakash, S.P. Singh, R.M. Claramunt, D. Sanz, I. Alkorta and J. Elguero, Tetrahedron, 61, 6642 (2005); https://doi.org/10.1016/j.tet.2005.03.035.
  23. Y. Rajendra Prasad, A. Lakshmana Rao, L. Prasoona, K. Murali and P. Ravi Kumar, Bioorg. Med. Chem. Lett., 15, 5030 (2005); https://doi.org/10.1016/j.bmcl.2005.08.040.
  24. S. Raghavan and K. Anuradha, Tetrahedron Lett., 43, 5181 (2002); https://doi.org/10.1016/S0040-4039(02)00972-3.
  25. B.A. Bohm, Introduction to Flavonoids, Harwood Academic: Amsterdam (1998).
  26. S. Ranganathan and J.E. Gready, J. Phys. Chem. B, 101, 5614 (1997); https://doi.org/10.1021/jp971051u.
  27. D. Ross, D. Siegel, H. Beall, A.S. Prakash, R.T. Mulcahy and N.W. Gibson, Cancer Metastasis Rev., 12, 83 (1993); https://doi.org/10.1007/BF00689803.
  28. T. Wymore, H.B. Nicholas and J. Hempel, J. Chem. Biol. Interact., 130-132, 201 (2001); https://doi.org/10.1016/S0009-2797(00)00278-7.
  29. M.A. Cunningham, L.L. Ho, D.T. Nguyen, R.E. Gillilan and P.A. Bash, Biochemistry, 36, 4800 (1997); https://doi.org/10.1021/bi962734n.
  30. Y. Murakami, J.-I. Kikuchi, Y. Hisaeda and O. Hayashida, Chem. Rev., 96, 721 (1996); https://doi.org/10.1021/cr9403704.
  31. N.J.A. Martin and B.J. List, J. Am. Chem. Soc., 128, 13368 (2006); https://doi.org/10.1021/ja065708d.
  32. J.W. Yang and B. List, Org. Lett., 8, 5653 (2006); https://doi.org/10.1021/ol0624373.
  33. S.-L. You, Chem. Asian J., 2, 820 (2007); https://doi.org/10.1002/asia.200700081.
  34. J.W. Yang, M.T. Hechavarria Fonseca and B. List, Angew. Chem. Int. Ed., 43, 6660 (2004); https://doi.org/10.1002/anie.200461816.
  35. J.B. Tuttle, S.G. Ouellet and D.W.C. MacMillan, J. Am. Chem. Soc., 128, 12662 (2006); https://doi.org/10.1021/ja0653066.
  36. D. Menche and F. Arikan, Synlett, 2006, 841 (2006); https://doi.org/10.1055/s-2006-939052.
  37. D. Menche, J. Hassfeld, J. Li, G. Menche, A. Ritter and S. Rudolph, Org. Lett., 8, 741 (2006); https://doi.org/10.1021/ol053001a.
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