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Rapid, green, and catalyst-free one-pot three-component syntheses of 5-substituted 1H-tetrazoles in magnetized water

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Abstract

The catalyst-free multi-component reactions of aldehydes, malononitrile, and sodium azide at a relatively low temperature in magnetized water provided 5-substituted 1H-tetrazoles in high-to-excellent yields. This method offers the advantages of short reaction times, low costs, quantitative reaction yields, simple work-up, green, and no need for any organic solvent.

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References

  1. R.J. Herr, Bioorg. Med. Chem. 10, 379 (2002)

    Article  Google Scholar 

  2. F. Ek, L.-G. Wistrand, T. Frejd, Tetrahedron 59, 6759 (2003)

    Article  CAS  Google Scholar 

  3. P. Rhonnstad, D. Wensbo, Tetrahedron Lett. 43, 3137 (2002)

    Article  CAS  Google Scholar 

  4. J.R. Maxwell, D.A. Wasdahl, A.C. Wolfson, V.I. Stenberg, J. Med. Chem. 27, 1565 (1984)

    Article  CAS  Google Scholar 

  5. D. Kundu, A. Majee, A. Hajra, Tetrahedron Lett. 50, 2668 (2009)

    Article  CAS  Google Scholar 

  6. W.K. Su, Z. Hong, W.G. Shan, X.X. Zhang, Eur. J. Org. Chem. 2006, 2723 (2006)

    Article  Google Scholar 

  7. S.N. Dighe, K.S. Jain, K.V. Srinivasan, Tetrahedron Lett. 50, 6139 (2009)

    Article  CAS  Google Scholar 

  8. S. Wu, A. Fluxe, J. Sheffer, J.M. Janusz, B.E. Blass, R. White, C. Jackson, R. Hedges, M. Murawsky, B. Fang, Bioorg. Med. Chem. Lett. 16, 6213 (2006)

    Article  CAS  Google Scholar 

  9. Y. Gu, R. De Sousa, G. Frapper, C. Bachmann, J. Barrault, F. Jerome, Green Chem. 11, 1968 (2009)

    Article  CAS  Google Scholar 

  10. B. Jiang, C. Li, F. Shi, S.-J. Tu, P. Kaur, W. Wever, G. Li, J. Org. Chem. 75, 2962 (2010)

    Article  CAS  Google Scholar 

  11. B. Jiang, S.-J. Tu, P. Kaur, W. Wever, G. Li, J. Am. Chem. Soc. 131, 11660 (2009)

    Article  CAS  Google Scholar 

  12. D. Enders, M.R. Huettl, C. Grondal, G. Raabe, Nature 441, 861 (2006)

    Article  CAS  Google Scholar 

  13. H. Torii, M. Nakadai, K. Ishihara, S. Saito, H. Yamamoto, Angew. Chem. 43, 1983 (2004)

    Article  CAS  Google Scholar 

  14. R. Breslow, Acc. Chem. Res. 37, 471 (2004)

    Article  CAS  Google Scholar 

  15. C.-J. Li, Chem. Rev. 105, 3095 (2005)

    Article  CAS  Google Scholar 

  16. L. Holysz, A. Szczes, E. Chibowski, J Colloid Interface Sci. 316, 996 (2007)

    Article  CAS  Google Scholar 

  17. M. Amiri, A.A. Dadkhah, Colloid Surf. A 278, 252 (2006)

    Article  CAS  Google Scholar 

  18. H.S. Grewal, B.L. Maheshwari, Bioelectromagnetics 32, 58 (2011)

    Article  Google Scholar 

  19. X.-F. Pang, B. Deng, B. Tang, Mod. Phys. Lett. 26, 1250069 (2012)

    Article  Google Scholar 

  20. S. Ozeki, J. Miyamoto, S. Ono, C. Wakai, T. Watanabe, J. Phys. Chem. 100, 4205 (1996)

    Article  CAS  Google Scholar 

  21. K.T. Chang, C.-I. Weng, J. Appl. Phys. 100, 043917 (2006)

    Article  Google Scholar 

  22. K. Zhou, G. Lu, Q. Zhou, J. Song, S. Jiang, H. Xia, J. Appl. Phys. 88, 1802 (2000)

    Article  CAS  Google Scholar 

  23. E. Chibowski, L. Hołysz, A. Szcześ, M. Chibowski, Colloid Surf. A 225, 63 (2003)

    Article  CAS  Google Scholar 

  24. J. Li, S. Luo, W. Yao, Z. Tang, Z. Zhang, M. Alim, J. Eur. Ceram. Soc. 24, 2605 (2004)

    Article  CAS  Google Scholar 

  25. T.R. Bastami, M.H. Entezari, Ultrason. Sonochem. 19, 830 (2012)

    Article  CAS  Google Scholar 

  26. M. Bakherad, A. Keivanloo, M. Gholizadeh, R. Doosti, M. Javanmardi, Res. Chem. Intermed. 43, 10113 (2017)

    Article  Google Scholar 

  27. S. Khaghaninejad, M.M. Heravi, T. Hosseinnejad, H.A. Oskooie, M. Bakavoli, Res. Chem. Intermed. 42, 1593 (2016)

    Article  CAS  Google Scholar 

  28. N. Ahmed, Z.N. Siddiqui, RSC Adv. 5, 16707 (2015)

    Article  CAS  Google Scholar 

  29. S. Maddila, K. Naicker, M.I.K. Momin, S. Rana, S. Gorle, S. Maddila, K. Yalagala, M. Singh, N.A. Koorbanally, S.B. Jonnalagadda, Med. Chem. Res. 25, 283 (2016)

    Article  CAS  Google Scholar 

  30. J. Safaei-Ghomi, S. Paymard-Samani, S. Zahedi, H. Shahbazi-Alavi, Z. Naturforsch. 70, 819 (2015)

    Article  CAS  Google Scholar 

  31. J. Safaei-Ghomi, S. Paymard-Samani, Chem. Heterocycl. Comp. 50, 1567 (2015)

    Article  CAS  Google Scholar 

  32. Z.N. Tisseh, M. Dabiri, M. Nobahar, H.R. Khavasi, Tetrahedron 68, 1769 (2012)

    Article  CAS  Google Scholar 

  33. J.K. Beattie, C.S. McErlean, C.B. Phippen, Chem. Eur. J. 16, 8972 (2010)

    Article  CAS  Google Scholar 

  34. A.C. Cefalas, E. Sarantopoulou, Z. Kollia, C. Riziotis, G. Dražic, S. Kobe, J. Stražišar, A. Meden, J. Comput. Theor. Nanosci. 7, 1800 (2010)

    Article  CAS  Google Scholar 

  35. K.X. Zhou, G.W. Lu, Q.C. Zhou, J.H. Song, S.T. Jiang, H.R. Xia, J. Appl. Phys. 88, 1802 (2000)

    Article  CAS  Google Scholar 

  36. S.V. Chen, Physics (China) 2, 109 (1992)

    Google Scholar 

  37. X.-F. Pang, Eur. Phys. J. B 49, 5 (2006)

    Article  CAS  Google Scholar 

  38. R.H. Cai, J. Yang, W. Zhu, J. Mol. Struct. 938, 15 (2009)

    Article  CAS  Google Scholar 

  39. Y.-Z. Guo, D.-C. Yin, H.-L. Cao, J.-Y. Shi, C.-Y. Zhang, Y.-M. Liu, H.H. Huang, Y. Liu, Y. Wang, W.-H. Guo, A.-R. Qian, P. Shang, Int. J. Mol. Sci. 13, 16916 (2012)

    Article  CAS  Google Scholar 

  40. J. Nakagawa, N. Hirota, K. Kitazawa, M. Shoda, J. Appl. Phys. 86, 2923 (1999)

    Article  CAS  Google Scholar 

  41. E.J.L. Toledo, T.C. Ramalho, Z.M. Magriotis, J. Mol. Struct. 888, 409 (2008)

    Article  CAS  Google Scholar 

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Acknowledgement

We gratefully acknowledge the financial support of the Research Council of the Shahrood University of Technology.

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Correspondence to Mohammad Bakherad.

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13738_2017_1193_MOESM1_ESM.docx

The supporting information for this work is available, as follows: copies of 1H and 13C spectra of all the new 5-substituted 1H-tetrazoles. (DOCX 3003 kb)

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Bakherad, M., Doosti, R., Keivanloo, A. et al. Rapid, green, and catalyst-free one-pot three-component syntheses of 5-substituted 1H-tetrazoles in magnetized water. J IRAN CHEM SOC 14, 2591–2597 (2017). https://doi.org/10.1007/s13738-017-1193-y

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