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Nanocrystalline magnesium oxide as a solid base catalyst promoted one pot synthesis of gem-dichloroaziridine derivatives under thermal conditions

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Abstract

In this study, efficient and mild synthesis of gem-dichloroaziridines from Schiff bases in the presence of nanocrystalline magnesium oxide/chloroform as a novel source of dichlorocarbene intermediate under thermal conditions have been described. The reaction is dramatically enhanced in the presence of nanocrystalline magnesium oxide, and any byproducts were detected during or after the reaction. The corresponding products have been obtained in excellent yields, high purity and short reaction times.

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References

  1. D. Gulkova, O. Solcova, M. Zdrazil, Microporous Mesoporous Mater. 76, 137 (2004)

    Article  CAS  Google Scholar 

  2. M.J. Climent, A. Corma, S. Iborra, M. Mifsud, J. Catal. 247, 223 (2007)

    Article  CAS  Google Scholar 

  3. A. Ganguly, P. Trinh, K.V. Ramanujachary, T. Ahmad, A.M.A.K. Ganguli, J. Colloid Interface Sci 353, 137 (2011)

    Article  CAS  Google Scholar 

  4. M.A. Faghihi-Sani, A. Yamaguchi, Ceram. Int. 28, 835 (2002)

    Article  CAS  Google Scholar 

  5. R. Chaim, Z.J. Shen, M.J. Nygren, Mater. Res. 19, 2527 (2004)

    Article  CAS  Google Scholar 

  6. D. Chen, E.H. Jordan, M. Gell, Scr Mater 59, 757 (2008)

    Article  CAS  Google Scholar 

  7. H. Hattori, Chem. Rev. 95, 537 (1995)

    Article  CAS  Google Scholar 

  8. B.M. Choudary, K.V.S. Ranganath, U. Pal, M.L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 127, 13167 (2005)

    Article  CAS  Google Scholar 

  9. M.L. Kantam, U. Pal, B. Sreedhar, B.M. Choudary, Adv. Synth. Catal. 349, 1671 (2007)

    Article  CAS  Google Scholar 

  10. B.M. Choudary, L.T. Chakrapani, K.V.R. Kumar, M.L. Kantum, Tetrahedron 62, 9571 (2006)

    Article  CAS  Google Scholar 

  11. D. Jain, A. Rani, Am. Chem. Sci. J. 1, 37 (2011)

    Google Scholar 

  12. M. Reddy, S. Ashoka, G. Chandrappa, M. Pasha, Catal. Lett. 138, 82 (2010)

    Article  CAS  Google Scholar 

  13. M. Seno, S. Shiraishi, Y. Suzuki, T. Asahara, Bull. Chem. Soc. Jpn. 51, 1413 (1978)

    Article  CAS  Google Scholar 

  14. O.S. Petrov, V.I. Ognyanov, N.M. Mollov, Synthesis 637 (1987)

  15. A.F. Khlebnikov, T.Yu. Nikiforova, M.S. Novikov, R.R. Kostikov, Synthesis 677 (1997)

  16. M.K. Meilahn, L.L. Augenstein, J.L. McManaman, J. Org. Chem. 36, 3627 (1971)

    Article  CAS  Google Scholar 

  17. Y. Ohshiro, H. Ohnishi, M. Komatsu, J. Jpn. Oil Chem. Soc. 36, 884 (1987)

    Article  CAS  Google Scholar 

  18. E.K. Fields, J.M. Sandri, Chem. Ind. (London). 1216 (1959)

  19. P.K. Kadaba, J.O. Edwards, J. Org. Chem. 25, 1431 (1960)

    Article  CAS  Google Scholar 

  20. A.G. Cook, E.K. Fields, J. Org. Chem. 27, 3686 (1962)

    Article  CAS  Google Scholar 

  21. M. Makosza, A. Kacprowicz, Rocz. Chem. 48, 2129 (1974)

    CAS  Google Scholar 

  22. A.F. Khlebnikov, M.S. Novikov, T.Yu. Nikiforova, R.R. Kostikov, Russ J. Org. Chem. 35, 91 (1999)

    CAS  Google Scholar 

  23. M.K. Meilahn, D.K. Olsen, W.J. Brittain, R.T. Anders, J. Org. Chem. 43, 1346 (1978)

    Article  CAS  Google Scholar 

  24. J. Graefe, Zeitsschrift Fuer Chemie 14, 469 (1974)

    CAS  Google Scholar 

  25. G.S. Singh, M. D’hooghe, N. De Kimpe, Chem. Rev. 107, 2080 (2007)

    Article  CAS  Google Scholar 

  26. E.Y. Shinkevich, K. Abbaspour Tehrani, A.F. Khlebnikov, M.S. Novikov, Tetrahedron 64, 7524 (2008)

    Article  CAS  Google Scholar 

  27. M. Mihara, Y. Ishino, S. Minakata, M. Komatsu, J. Org. Chem. 70, 5320 (2005)

    Article  CAS  Google Scholar 

  28. H. Naeimi, F. Salimi, Kh. Rabiei, J. Mol. Catal. A Chem 260, 100 (2006)

    Article  CAS  Google Scholar 

  29. H. Naeimi, H. Sharghi, F. Salimi, Kh. Rabiei, Heteroatom Chem. 19, 43 (2008)

    Article  CAS  Google Scholar 

  30. F. Meshkani, M. Rezaei, Powder Technol. 196, 85 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to University of Kashan for supporting this work by Grant No. 159148/3.

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Correspondence to H. Naeimi.

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Naeimi, H., Rabiei, K., Rezaei, M. et al. Nanocrystalline magnesium oxide as a solid base catalyst promoted one pot synthesis of gem-dichloroaziridine derivatives under thermal conditions. J IRAN CHEM SOC 10, 161–167 (2013). https://doi.org/10.1007/s13738-012-0137-9

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  • DOI: https://doi.org/10.1007/s13738-012-0137-9

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