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Hydrotrope promoted in situ azidonation followed by copper catalyzed regioselective synthesis of β-hydroxytriazoles

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Abstract

The rapid method for the synthesis of organic azides was achieved by employing azide acceptors such as halides, epoxides and pseudohalides like diazonium salts and aryl boronic acids in hydrotropic media. In extension, the sequential multicomponent reaction of epoxides, azide and alkynes using copper catalysis has been discussed. The reaction proceeds via the in situ generation of azido-alcohol followed by synthesis of chiral β-hydroxytriazoles. This [3 + 2] cycloaddition reaction of azide and alkyne using copper catalysis serves as a green and efficient protocol in “Click Chemistry”. The nucleophilic addition of azide to epoxide and alkyne-azide cycloaddition is the two simultaneous regioselective click reactions observed in the proposed method.

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References

  1. P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice (Oxford University Press, Oxford, 1998)

    Google Scholar 

  2. P.R. Boruah, A.A. Ali, B. Saikia, D. Sarma, Green Chem. 17, 1442 (2015)

    Article  CAS  Google Scholar 

  3. A. Kumar, R.D. Shukla, Green Chem. 17, 848 (2015)

    Article  CAS  Google Scholar 

  4. G. Lu, C. Cai, B.H. Lipshutz, Green Chem. 15, 105 (2013)

    Article  CAS  Google Scholar 

  5. K. Szabo, P. Wang, B. Peles-Lemli, Y. Fang, L. Kollar, S. Kunsagi-Mate, Colloids Surf. A Physicochem. Eng. Asp. 422, 143 (2013)

    Article  CAS  Google Scholar 

  6. S. Kumar, N. Parveen, K. Din, J. Surfactants Deterg. 8, 109 (2005)

    Article  CAS  Google Scholar 

  7. S.E. Friberg, C. Brancewicz, Langmuir 10, 2945 (1994)

    Article  CAS  Google Scholar 

  8. S. Brase, C. Gil, K. Knepper, V. Zimmerman, Angew. Chem. Int. Ed. 44, 5188 (2005)

    Article  CAS  Google Scholar 

  9. E.F.V. Scriven, K. Turnbull, Chem. Rev. 88, 297 (1988)

    Article  CAS  Google Scholar 

  10. Y. Ju, D. Kumar, R.S. Varma, J. Org. Chem. 71, 6697 (2006)

    Article  CAS  Google Scholar 

  11. M. Zarchi, Z. Escandari, J. Appl. Polym. Sci. 121, 1916 (2011)

    Article  CAS  Google Scholar 

  12. W. Zhu, D. Ma, Chem. Commun. 7, 888–889 (2004)

    Article  Google Scholar 

  13. G. Sabitha, R. Satheesh Babu, S.M. Rajkumar, J.S. Yadav, Org. Lett. 4, 343 (2002)

    Article  CAS  Google Scholar 

  14. Q. Wu, L. Wang, Synthesis 13, 2007 (2008)

    Google Scholar 

  15. Q. Zhang, D. Wang, X. Wang, K. Ding, J. Org. Chem. 74, 7187 (2009)

    Article  CAS  Google Scholar 

  16. Y. Zhang, X. Yang, Q. Yao, D. Ma, Org. Lett. 14, 3056 (2012)

    Article  CAS  Google Scholar 

  17. A. Sujatha, A.M. Thomas, A.P. Thankachan, G. Anilkumar, ARKIVOC 1 (2015)

  18. G. Evano, C. Theunissen, A. Pradal, Nat. Prod. Rep. 30, 1467 (2013)

    Article  CAS  Google Scholar 

  19. M. Meldal, C.W. Tornoe, Chem. Rev. 108, 2952 (2008)

    Article  CAS  Google Scholar 

  20. J.E. Hein, V.V. Fokin, Chem. Soc. Rev. 39, 1302 (2010)

    Article  CAS  Google Scholar 

  21. J.E. Moses, A.D. Moorhouse, Chem. Soc. Rev. 36, 1249 (2007)

    Article  CAS  Google Scholar 

  22. H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004 (2001)

    Article  CAS  Google Scholar 

  23. S. Lober, P. Rodrigues-Loaiza, P. Gmeiner, Org. Lett. 5, 1753 (2003)

    Article  Google Scholar 

  24. N. Li, P. Zhao, N. Liu, M. Echeverria, S. Moya, L. Salmon, J. Ruiz, D. Astruc, Chem. Eur. J. 20, 8363 (2014)

    Article  CAS  Google Scholar 

  25. L. Zhang, X. Chen, P. Xue, H.H.Y. Sun, I.D. Williams, K.B. Sharpless, V.V. Fokin, G. Jia, J. Am. Chem. Soc. 127, 15998 (2005)

    Article  CAS  Google Scholar 

  26. F. Alonso, Y. Moglie, G. Radivoy, M. Yus, J. Org. Chem. 76, 8394 (2011)

    Article  CAS  Google Scholar 

  27. K. Kamata, Y. Nakagawa, K. Yamaguchi, N. Mizuno, J. Am. Chem. Soc. 130, 15304 (2008)

    Article  CAS  Google Scholar 

  28. L.S. Campbell-Verduyn, W. Szymański, C.P. Postema, R.A. Dierckx, P.H. Elsinga, D.B. Janssen, B.L. Feringa, Chem. Commun. 46, 898 (2010)

    Article  CAS  Google Scholar 

  29. A.N. Prasad, B. Thirupathi, G. Raju, R. Srinivas, B.M. Reddy, Catal. Sci. Technol. 2, 1264 (2012)

    CAS  Google Scholar 

  30. H. Naeimi, V. Nejadshafiee, New J. Chem. 38, 5429 (2014)

    Article  CAS  Google Scholar 

  31. P. Thirumurugan, D. Matosiuk, K. Jozwiak, Chem. Rev. 113, 4905 (2013)

    Article  CAS  Google Scholar 

  32. R. Alvarez, S. Velazques, A. San-Felix, S. Aquaro, E.D. Clercq, C. Perno, A. Karlsson, J. Balzarini, M.J. Camarasa, J. Med. Chem. 37, 4185 (1994)

    Article  CAS  Google Scholar 

  33. D.R. Buckle, C.J.M. Rockell, H. Smith, B.A. Spicer, J. Med. Chem. 29, 2262 (1986)

    Article  CAS  Google Scholar 

  34. F. Musumeci, S. Schenone, A. Desogus, E. Nieddu, D. Deodato, L. Botta, Curr. Med. Chem. 22, 2022 (2015)

    Article  CAS  Google Scholar 

  35. M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.A. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert, B.H. Yagi, J. Med. Chem. 43, 953 (2000)

    Article  CAS  Google Scholar 

  36. A. Brik, J. Alexandratos, Y.C. Lin, J.H. Elder, A.J. Olson, A. Wlodawer, D.S. Goodsell, C.H. Wong, ChemBioChem 6, 1167 (2005)

    Article  CAS  Google Scholar 

  37. A.J. Link, D.A. Tirrell, J. Am. Chem. Soc. 125, 11164 (2003)

    Article  CAS  Google Scholar 

  38. P.K. Avti, D. Maysinger, A. Kakkar, Molecules 18, 9531 (2013)

    Article  CAS  Google Scholar 

  39. D.P. Temelkoff, M. Zeller, P. Norris, Carbohydr. Res. 341, 1081 (2006)

    Article  CAS  Google Scholar 

  40. L. Marmuse, S.A. Nepogodiev, R.A. Field, Org. Biomol. Chem. 3, 2225 (2005)

    Article  CAS  Google Scholar 

  41. P. Wu, A.K. Feldman, A.K. Nugent, C.J. Hawker, A. Scheel, B. Voit, J. Pyun, J.M.J. Fréchet, K.B. Sharpless, V.V. Fokin, Angew. Chem. Int. Ed. 43, 3928 (2004)

    Article  CAS  Google Scholar 

  42. A. Patil, M. Barge, G. Rashinkar, R. Salunkhe, Mol Divers 19, 435 (2015)

    Article  CAS  Google Scholar 

  43. S.B. Kamble, A.S. Kumbhar, G.S. Rashinkar, M.S. Barge, R.S. Salunkhe, Ultrason. Sonochem. 19, 812 (2012)

    Article  CAS  Google Scholar 

  44. A.S. Kumbhar, S.B. Kamble, M.S. Barge, G.S. Rashinkar, R.S. Salunkhe, Tetrahedron Lett. 53, 2756 (2012)

    Article  CAS  Google Scholar 

  45. B. Furnis, A. Hannaford, P. Smith, A. Tatchell, Vogel’s Textbook of Practical Organic Chemistry (Prentice Hall, Upper Saddle River, 1996), p. 925

    Google Scholar 

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Acknowledgements

The authors thank UGC, New Delhi for financial assistance [F. No. 41-310/2012 (SR)].

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Authors and Affiliations

  1. Department of Chemistry, Shivaji University, Kolhapur, MS, 416004, India

    Amol Patil & Rajashri Salunkhe

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  1. Amol Patil
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  2. Rajashri Salunkhe
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Correspondence to Rajashri Salunkhe.

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Patil, A., Salunkhe, R. Hydrotrope promoted in situ azidonation followed by copper catalyzed regioselective synthesis of β-hydroxytriazoles. Res Chem Intermed 43, 4175–4187 (2017). https://doi.org/10.1007/s11164-017-2871-1

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