Issue

Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018

Copyright (c) 2018 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Highly Effective Opening of Epoxides with Aromatic Amines in Presence of β-Cyclodextrin in Water

https://doi.org/10.14233/ajchem.2018.21260
Siping Tang
Department of Chemistry and Material Science, Hengyang Normal University, Hengyang 421008, Hunan Province, P.R. China; Key Laboratory of Functional Organometallic Materials of Hunan Province, Hengyang 421008, Hunan Province, P.R. China
Zhifeng Xu
Department of Chemistry and Material Science, Hengyang Normal University, Hengyang 421008, Hunan Province, P.R. China; Key Laboratory of Functional Organometallic Materials of Hunan Province, Hengyang 421008, Hunan Province, P.R. China
Junhua Li
Department of Chemistry and Material Science, Hengyang Normal University, Hengyang 421008, Hunan Province, P.R. China; Key Laboratory of Functional Organometallic Materials of Hunan Province, Hengyang 421008, Hunan Province, P.R. China
Peihong Deng
Department of Chemistry and Material Science, Hengyang Normal University, Hengyang 421008, Hunan Province, P.R. China; Key Laboratory of Functional Organometallic Materials of Hunan Province, Hengyang 421008, Hunan Province, P.R. China
Lanyong Feng
Department of Chemistry and Material Science, Hengyang Normal University, Hengyang 421008, Hunan Province, P.R. China; Key Laboratory of Functional Organometallic Materials of Hunan Province, Hengyang 421008, Hunan Province, P.R. China

Corresponding Author(s) : Siping Tang

tsp00@163.com

Asian Journal of Chemistry, Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018

Abstract

This paper reports a simple, mild, and convenient method to synthesize β-amino alcohols. These β-amino alcohols were achieved in excellent yields (80-96 %) by ring-opening reaction of oxiranes with aromatic amines catalyzed by β-cyclodextrin at 30 ºC in water. β-cyclodextrin as the catalyst greatly accelerated the reactions and can be recovered and reused.

Keywords

Oxiranes β-Cyclodextrin β-Amino alcohols Ring-opening
Tang, S., Xu, Z., Li, J., Deng, P., & Feng, L. (2018). Highly Effective Opening of Epoxides with Aromatic Amines in Presence of β-Cyclodextrin in Water. Asian Journal of Chemistry, 30(5), 1165–1170. https://doi.org/10.14233/ajchem.2018.21260
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. P. O’Brien, Angew. Chem. Int. Ed., 38, 326 (1999); https://doi.org/10.1002/(SICI)1521-3773(19990201)38:3<326::AIDANIE326>3.0.CO;2-T.
  2. G. Li, H.T. Chang and K.B. Sharpless, Angew. Chem. Int. Ed. Engl., 35, 451 (1996); https://doi.org/10.1002/anie.199604511.
  3. D.J. Ager, I. Prakash and D.R. Schaad, Chem. Rev., 96, 835 (1996); https://doi.org/10.1021/cr9500038.
  4. J.A. Deyrup and C.L. Moyer, J. Org. Chem., 34, 175 (1969); https://doi.org/10.1021/jo00838a038.
  5. C.L. Kissel and B. Rickborn, J. Org. Chem., 37, 2060 (1972); https://doi.org/10.1021/jo00978a002.
  6. M.C. Carre, J.P. Houmounou and P. Caubere, Tetrahedron Lett., 26, 3107 (1985); https://doi.org/10.1016/S0040-4039(00)98630-1.
  7. J. Yamada, M. Yumoto and Y. Yamamoto, Tetrahedron Lett., 30, 4255 (1989); https://doi.org/10.1016/S0040-4039(01)80704-8.
  8. J. Auge and F. Leroy, Tetrahedron Lett., 37, 7715 (1996); https://doi.org/10.1016/0040-4039(96)01731-5.
  9. M. Chini, P. Crotti, L. Favero, F. Macchia and M. Pineschi, Tetrahedron Lett., 35, 433 (1994); https://doi.org/10.1016/0040-4039(94)85073-9.
  10. A.T. Placzek, J.L. Donelson, R. Trivedi, R.A. Gibbs and S.K. De, Tetrahedron Lett., 46, 9029 (2005); https://doi.org/10.1016/j.tetlet.2005.10.106.
  11. G. Sundararajan, K. Vijayakrishna and B. Varghese, Tetrahedron Lett., 45, 8253 (2004); https://doi.org/10.1016/j.tetlet.2004.09.023.
  12. A.K. Chakraborti and A. Kondaskar, Tetrahedron Lett., 44, 8315 (2003); https://doi.org/10.1016/j.tetlet.2003.09.046.
  13. N.R. Swamy, T.V. Goud, S.M. Reddy, Y. Venkateswarlu and P. Krishnaiah, Synth. Commun., 34, 727 (2004); https://doi.org/10.1081/SCC-120027721.
  14. L.D. Pachón, P. Gamez, J.J.M. van Brussel and J. Reedijk, Tetrahedron Lett., 44, 6025 (2003); https://doi.org/10.1016/S0040-4039(03)01480-1.
  15. N. Tan, S. Yin, Y. Li, R. Qiu, Z. Meng, X. Song, S. Luo, C.-T. Au and W.-Y. Wong, J. Organomet. Chem., 696, 1579 (2011); https://doi.org/10.1016/j.jorganchem.2010.12.035.
  16. A. Kamal, R. Ramu, M.A. Azhar and G.B.R. Khanna, Tetrahedron Lett., 46, 2675 (2005); https://doi.org/10.1016/j.tetlet.2005.02.073.
  17. J.S. Yadav, B.V.S. Reddy, A.K. Basak and A.V. Narsaiah, Tetrahedron Lett., 44, 1047 (2003); https://doi.org/10.1016/S0040-4039(02)02735-1.
  18. S.R. Kumar and P. Leelavathi, J. Mol. Catal. Chem., 266, 65 (2007); https://doi.org/10.1016/j.molcata.2006.10.045.
  19. S.S. Chimni, N. Bala, V.A. Dixit and P.V. Bharatam, Tetrahedron, 66, 3042 (2010); https://doi.org/10.1016/j.tet.2010.02.053.
  20. R.I. Kureshy, S. Agrawal, M. Kumar, N.H. Khan, S.H.R. Abdi and H.C. Bajaj, Catal. Lett., 134, 318 (2010); https://doi.org/10.1007/s10562-009-0237-z.
  21. S.P. Tang, P. Hu, H.Y. Chen, S. Chen, Z.W. Mao and L.N. Ji, J. Mol. Catal. Chem., 335, 222 (2011); https://doi.org/10.1016/j.molcata.2010.11.037.
  22. S.-P. Tang, S. Chen, G.-F. Wu, H.-Y. Chen, Z.-W. Mao and L.-N. Ji, Inorg. Chem. Commun., 14, 184 (2011); https://doi.org/10.1016/j.inoche.2010.10.018.
  23. S.-P. Tang, Y.-H. Zhou, H.-Y. Chen, C.-Y. Zhao, Z.-W. Mao and L.-N. Ji, Chem. Asian J., 4, 1354 (2009); https://doi.org/10.1002/asia.200900108.
  24. M. Moghadam, S. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S. Gorjipoor and P. Yazdani, Synth. Commun., 39, 552 (2009); https://doi.org/10.1080/00397910802406729.
  25. M. Maheswara, K.S.V.K. Rao and J.Y. Do, Tetrahedron Lett., 49, 1795 (2008); https://doi.org/10.1016/j.tetlet.2008.01.044.
  26. M. Vijender, P. Kishore, P. Narender and B. Satyanarayana, J. Mol. Catal. Chem., 266, 290 (2007); https://doi.org/10.1016/j.molcata.2006.09.006.
  27. G.R. Krishnan, K.S. Kajal and K. Sreekumar, Monatsh. Chem., 143, 637 (2012); https://doi.org/10.1007/s00706-011-0628-x.
  28. L.R. Reddy, M.A. Reddy, N. Bhanumathi and K.R. Rao, New J. Chem., 25, 221 (2001); https://doi.org/10.1039/b007729l.
  29. A. Kamal, B.R. Prasad, A.M. Reddy and M.N.A. Khan, Catal. Commun., 8, 1876 (2007); https://doi.org/10.1016/j.catcom.2007.02.029.
  30. R. Sridhar, B. Srinivas, K. Surendra, N.S. Krishnaveni and K.R. Rao, Tetrahedron Lett., 46, 8837 (2005); https://doi.org/10.1016/j.tetlet.2005.10.094.
Read More
Author biographies is not available.
Download
PDF
Statistic
Read Counter : 0 Download : 0