Copper (0) an Efficient Catalyst for the Synthesis of Biologically Active 1, 2- Amino Alcohols

Authors

  • Santosh S. Devkate  Department of Chemistry, S. M. Joshi college Hadapsar, Pune, Maharashtra, India
  • Arvind S. Burungale  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Ashok S. Pise  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Ramesh B. Gawade  Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Mohan B. Kale2   Department of Chemistry, S. M. Joshi College Hadapsar, Pune, Maharashtra, India
  • Sunil D. Jadhav  Department of Chemistry, M. P.A.C.S. College Panvel, Raigad, Maharashtra, India

Keywords:

Copper (0), Napthalenide, Epoxide, Eugenol, Amino Alcohol, Biological Activity, Spectroscopy.

Abstract

The regioselective epoxide ring opening with nucleophiles like amines gives well known 1, 2-difunctionalized amino alcohols. These are present in many natural and synthetic products. The ring opening of epoxide is achieved by cleavage with amine in presence of copper (0) as a catalyst. We have observed that lithium napthalenide reduction of copper (I) produces a highly reactive form of copper (0) that acts as a catalyst for ring opening of epoxides with an amine.

References

  1. Liebscher, J. et. Al. synthetic applications of chiral pool derived heterocycles. J. Heterocyclic Chem. 2000, 37, 509-518.
  2. Corey, E. J; Zhang, F; Org. Lett, 1999, 1, 1287-1290.
  3. V. T. Kamble; N. S. Joshi; Green Chemistry Letters and Reviews, 2010, 3-4, 275-281.
  4. Connolly, M. E; et. Al. Prog. Cardiovasc Dis. 1976, 19, 203-234.
  5. Michael J. P; Indolizidine and Quinolizidine alkaloids. Nat. Prod. Rep, 2001, 18, 520- 542.
  6. Anil K. Kinage, Pravin P. Upare, Anaandkumar B. Shivarkar, Sunil P. Gupte, Green and Sustainable Chemistry, 2011, 1, 7684.
  7. Shivani, B; Pujala, A. K; Chakraborti, J. Org Chem., 2007, 72, 3713-3722.
  8. N. Azizi; M. R. Saidi, Org. Lett. 2005, 7, 3649-3651.
  9. J. R. Lizza, G. Moura-Letts, Synthesis, 2017, 49, 1231-1242.
  10. S. Azoulay, K. Manabe, S. Kobayashi, Org. Lett., 2005, 7, 4593-4595.
  11. Bergmeier, S. C; Tetrahedron, 2000, 56, 2561-2576.
  12. A. Heydari, M. Mehrdad, A. Maleki, N. Ahmadi; Synthesis, 2004, 1557-1558.
  13. M. Kumar, R. I. Kureshy, S. Saravanan, S. Verma, A. Jakhar, N. H. Khan, S. H. R. Abdi, H. C. Bajaj, Org Lett. 2014, 16, 2798-2801.
  14. Ager, D.J; Prakash, I; Schaad D. R; Chem. Rev. 1996, 96, 835-875.
  15. A, k. Chakraborti, S. Rudrawar, A. Kondaskar, Org. Biomol. Chem. 2004, 2, 1277-1280.
  16. H. Y. Kim, A. Talukdar, M. Cushman; Org. Lett. 2006, 8, 1085-1087.
  17. A. B. Shivarkar, S. P. Gupte, R. V. Chaudhari, Synlett, 2006, 1374-1378.
  18. C. Wang, H. Yamamoto, J. Am. Chem. Soc., 2014, 136, 6888-6891.
  19. Mark Ruschgen Klaas; Siegfried Warwel, Org. Lett., 1999, 1, 1025-1026.
  20. Ahmed Kamal, R. Ramu, Mohd. Ameruddin Azhar, G. B. Ramesh Khanna, Tetrahedron Letters, 2005, 46, 2675-2677.
  21. Li, G; Chang, H. T; Sharpless, B. K; Angew; Chem. Int. Ed. 1996, 35, 451-454.
  22. Huirong Yao, David E. Richardson, J. Am. Chem. Soc. 2000, 122, 3220-3221.
  23. Murphy A, Pace A, Stack T. D. P., Org. Lett., 2004, 6, 3139.
  24. Lindstrom, U. M; Franckowiak, R; Pinault, N; Somfai, P; Tetrahedron Lett. 1997, 38, 2027-2030.
  25. Liu Y, Murata K, Inaba M., J. Chem. Soc. Chem. Commun. , 2004, 582.
  26. Kan J. T.W; Toy P. H; Tetrahedron Lett. , 2004, 45, 6357.
  27. Shi Y; Acc. Chem. Res., 2004, 37, 488.
  28. Deyrup, J. A; Moyer, C. L; J. Org. Chem. 1969, 34, 175-179.
  29. Behrevs, C. H; Ko, S. Y; Sharpless, K. B; Walker, F. J; J. Org. Chem. 1985, 50, 5687.
  30. Rieke R. D; Rhyne L. D; J. Org. Chem., 1984,49, 3445.

International Journal of Scientific Research in Science and Technology

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Published

2018-02-28

Issue

Volume 4, Issue 2, January-February-2018

Section

Research Articles

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How to Cite

[1]
Santosh S. Devkate, Arvind S. Burungale, Ashok S. Pise, Ramesh B. Gawade, Mohan B. Kale2 , Sunil D. Jadhav, " Copper (0) an Efficient Catalyst for the Synthesis of Biologically Active 1, 2- Amino Alcohols, International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011, Volume 4, Issue 2, pp.270-274, January-February-2018.