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

Authors(6) :-Santosh S. Devkate, Arvind S. Burungale, Ashok S. Pise, Ramesh B. Gawade, Mohan B. Kale2 , Sunil D. Jadhav

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.

Authors and Affiliations

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

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

  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.

Publication Details

Published in : Volume 4 | Issue 2 | January-February 2018
Date of Publication : 2018-02-28
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 270-274
Manuscript Number : IJSRST184157
Publisher : Technoscience Academy

Print ISSN : 2395-6011, Online ISSN : 2395-602X

Cite This Article :

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), Print ISSN : 2395-6011, Online ISSN : 2395-602X, Volume 4, Issue 2, pp.270-274, January-February-2018. Available at doi : 10.32628/IJSRST184157
Journal URL : http://ijsrst.com/IJSRST184157

Article Preview

Contact Us