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One-pot three-component reaction for efficient and facile synthesis of γ-nitrocarbonyl compounds under solvent-free conditions

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Chemical Research in Chinese Universities Aims and scope

Abstract

A simple and efficient protocol was established to synthesize γ-nitrocarbonyl compounds via three-component one-pot tandem condensation reaction of aldehydes, Meldrum’s acid and nitroalkanes under solvent-free conditions. The present method shows fascinating features such as using readily available starting materials, promoting the yields by inexpensive and mild organic base triethylamine, omiting the synthesis of Michael acceptor and avoiding the use of organic solvent. This strategy provides an easy alternative synthetic approach to the useful intermediate, γ-nitrocarbonyl compounds, with moderate to good yields.

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References

  1. Mitchell C. E. T., Brenner S. E., Ley S. V., Chem. Commun., 2005, 41(42), 5346

    Article  Google Scholar 

  2. Mei K., Jin M., Zhang S., Li P., Liu W., Chen X., Xue F., Duan W., Wang W., Org. Lett., 2009, 11(13), 2864

    Article  CAS  Google Scholar 

  3. Roca-Lopez D., Sadaba D., Delso I., Herrera R. P., Tejero T., Merino P., Tetrahedron: Asymmetry, 2010, 21(21/22), 2561

    Article  CAS  Google Scholar 

  4. Ballini R., Bosica G., Fiorini D., Palmieri A., Petrini M., Chem. Rev., 2005, 105(3), 933

    Article  CAS  Google Scholar 

  5. Krishna P. R., Sreeshailam A., Srinivas R., Tetrahedron, 2009, 65(47), 9657

    Article  CAS  Google Scholar 

  6. Lia J. H., Li Z. G., Chen Q. G., J. Chem. Res., 2004, 758

    Google Scholar 

  7. Bassas O., Huuskonen J., Rissanen K., KosKinen A. M. P., Eur. J. Org. Chem., 2009, 1340

    Google Scholar 

  8. Didiera D., Sergeyev S., Arkivoc, 2009, (xiv), 124

    Google Scholar 

  9. Kataja A. O., Koskinen A. M. P., Arkivoc, 2010, (ii), 205

    Google Scholar 

  10. Lou H. W., Zhang T., Li K., Zhang M., Li J. H., Chin. J. Org. Chem., 2011, 31(8), 1258

    CAS  Google Scholar 

  11. Leyva-Pérez A., García-García P., Corma A., Angew. Chem. Int. Ed., 2014, 53(33), 8687

    Article  Google Scholar 

  12. Schreiber S. L., Science, 2000, 287(5460), 1964

    Article  CAS  Google Scholar 

  13. Wen L. R., Li Z. R., Li M., Cao H., Green Chem., 2012, 14(3), 707

    Article  CAS  Google Scholar 

  14. Jiang B., Rajale T., Wever W., Tu S. J., Li G. G., Chem. Asian J., 2010, 5(11), 2318

    Article  CAS  Google Scholar 

  15. Lin X. F., Mao Z. J., Dai X. X., Lu P., Wang Y. G., Chem. Commun., 2011, 47(23), 6620

    Article  CAS  Google Scholar 

  16. Hong D., Zhu Y. X., Li Y., Lin X. F., Lu P., Wang Y. G., Org. Lett., 2011, 13(17), 4668

    Article  CAS  Google Scholar 

  17. Ghahremanzadeh R., Rashid Z., Zarnani A. H., Naeimi H., Ultrason. Sonochem., 2014, 21(4), 1451

    Article  CAS  Google Scholar 

  18. Toure B. B., Hall D. G., Chem. Rev., 2009, 109(9), 4439

    Article  CAS  Google Scholar 

  19. Candeias N. R., Montalbano F., Cal P. M., Gois P. M. P., Chem. Rev., 2010, 110(10), 6169

    Article  CAS  Google Scholar 

  20. Ramachary D. B., Jain S., Org. Biomol. Chem., 2011, 9(5), 1277

    Article  CAS  Google Scholar 

  21. Bonfield E. R., Li C. J., Adv. Synth. Catal., 2008, 350(3), 370

    Article  CAS  Google Scholar 

  22. Elders N., vander Born D., Hendrickx L. J. D., Timmer B. J. J., Krause A., Janssen E., de Kanter F. J. J., Ruijter E., Orru R. V. A., Angew. Chem. Int. Ed., 2009, 48(32), 5856

    Article  CAS  Google Scholar 

  23. Brahmachari G., Das S., Tetrahedron Lett., 2012, 53(12), 1479

    Article  CAS  Google Scholar 

  24. Deng H., Li Z., Ke F., Zhou X., Chem. Eur. J., 2012, 18(16), 4840

    Article  CAS  Google Scholar 

  25. Sunderhaus J. D., Dockendorff C., Martin S. F., Tetrahedron, 2009, 65(33), 6454

    Article  CAS  Google Scholar 

  26. Tu X. C., Feng H., Tu M. S., Jiang B., Wang S. L., Tu S. J., Tetrahedron Lett., 2012, 53(25), 3169

    Article  CAS  Google Scholar 

  27. Yu J., Shi F., Gong L. Z., Acc. Chem. Res., 2011, 44(11), 1156

    Article  CAS  Google Scholar 

  28. Dömling A., Wang W., Wang K., Chem. Rev., 2012, 112(6), 3083

    Article  Google Scholar 

  29. Hajipour A. R., Ghayeb Y., Sheikhan N., Tetrahedron Lett., 2009, 50(40), 5649

    Article  CAS  Google Scholar 

  30. Jiang B., Xue L. Y., Wang X. H., Tu M. S., Liu Y. P., Tu S. J., Tetrahedron Lett., 2012, 53(10), 1261

    Article  CAS  Google Scholar 

  31. Aditya K., Béla T., Green Chem., 2010, 12(5), 875

    Article  Google Scholar 

  32. Ma N., Jiang B., Zhang G., Tu S. J., Wever W., Li G. G., Green Chem., 2010, 12(8), 1357

    Article  CAS  Google Scholar 

  33. Cheng C., Jiang B., Tu S. J., Li G. G., Green Chem., 2011, 13(8), 2107

    Article  CAS  Google Scholar 

  34. Martins M. A. P., Frizzo C. P., Moreira D. N., Buriol L., Machado P., Chem. Rev., 2009, 109(9), 4140

    Article  CAS  Google Scholar 

  35. Kumar R., Raghuvanshi K., Verma R. K., Singh M. S., Tetrahedron Lett., 2010, 51(45), 5933

    Article  CAS  Google Scholar 

  36. Kidwai M., Jahan A., Chauhan R., Mishra N. K., Tetrahedron Lett., 2012, 53(14), 1728

    Article  CAS  Google Scholar 

  37. Wen L. R., Li Z. R., Li M., Cao H., Green Chem., 2012, 14(3), 707

    Article  CAS  Google Scholar 

  38. Zong C. L., Zeng R. S., Zou J. P., Chem. Res. Chinese Universities, 2014, 30(4), 632

    Article  CAS  Google Scholar 

  39. Poe S. L., Kobašlija M., McQuade D. T., J. Am. Chem. Soc., 2006, 128(49), 15586

    Article  CAS  Google Scholar 

  40. Poe S. L., Kobašlija M., McQuade D. T., J. Am. Chem. Soc., 2007, 129(29), 9216

    Article  CAS  Google Scholar 

  41. Li Y. L., Zhao B., Du B. X., Jiang Q. S., Wang X. S., Cao C. S., Tetrahedron Lett., 2013, 54(3), 227

    Article  CAS  Google Scholar 

  42. Gusarova N. K., Volkov P. A., Ivanova N. I., Sukhov B. G., Larina L. I., Kazheva O. N., Alexandrov G. G., D’yachenko O. A., Trofimov B. A., Tetrahedron Lett., 2013, 54(49), 6772

    Article  CAS  Google Scholar 

  43. Yavari I., Beheshti S., Hossaini Z., Souri S., Synth. Commun., 2011, 41(6), 907

    Article  CAS  Google Scholar 

  44. Wassima G., Raouf B., Abdelmadjid D., Chin. J. Chem., 2012, 30(3), 733

    Article  Google Scholar 

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Authors and Affiliations

  1. Shcool of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian, 116029, P. R. China

    Chengwei Lü, Yanhang Liu, Xiaoxia Zhou & Jiajing Wang

Authors
  1. Chengwei Lü
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  2. Yanhang Liu
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  3. Xiaoxia Zhou
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  4. Jiajing Wang
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Corresponding author

Correspondence to Chengwei Lü.

Additional information

Supported by the National Natural Science Foundation of China(No.21403100) and the Doctoral Scientific Research Foundation of Liaoning Province, China(No.20141100).

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Lü, C., Liu, Y., Zhou, X. et al. One-pot three-component reaction for efficient and facile synthesis of γ-nitrocarbonyl compounds under solvent-free conditions. Chem. Res. Chin. Univ. 31, 208–211 (2015). https://doi.org/10.1007/s40242-015-4410-1

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  • DOI: https://doi.org/10.1007/s40242-015-4410-1

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