Skip to main content

Advertisement

SpringerLink
Log in

Protonated Mesoporous Aluminosilica Nanospheres Boosting Aza-Michael Cyclization and Diels-Alder Reaction

  • Article
  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

Mesoporous aluminosilica hollow nanospheres were prepared easily, which possess very strong acid site. The heterogeneous catalyst can be utilized in both intramolecular aza-Michael addition cyclization and intermolecular Diels-Alder reaction. The catalyst could be easily recovered and reused. Furthermore, the catalyst could be used in continuous flow chemistry for the uninterrupted synthesis of 2,3-dihydroquinolin-4(1H)-ones, which disclosed the potential application of the present solid catalyst in both academic and industrial syntheses. In addition, the catalyst could be recovered and reused at least 7 times without obvious loss of activity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Katritzky A. R., Rachwal S., Rachwal B., Tetrahedron, 1996, 52, 15031.

    Article  CAS  Google Scholar 

  2. Nicolaou K. C., Edmonds D. J., Bulger P. G., Angew. Chem. Int. Ed., 2006, 45, 7134.

    Article  CAS  Google Scholar 

  3. Tkes A. L., Szilágyi L., Synthetic. Commun., 1987, 17, 1235.

    Article  Google Scholar 

  4. Donnelly J. A., Farrell D. F., J. Org. Chem., 1990, 55, 1757.

    Article  CAS  Google Scholar 

  5. Liu X., Lu Y., Org. Lett., 2010, 12, 5592.

    Article  CAS  PubMed  Google Scholar 

  6. Bunce R. A., Nammalwar B., J. Heterocyclic. Chem., 2011, 48, 613.

    Article  CAS  Google Scholar 

  7. Pisaneschi F., Sejberg J. J. P., Blain C., Ng W. H., Aboagye E. O., Spivey A. C., Synlett, 2011, 2011, 241.

    Article  Google Scholar 

  8. Nammalwar B., Bunce R., Molecules, 2014, 19, 204.

    Article  Google Scholar 

  9. Saito K., Moriya Y., Akiyama T., Org. Lett., 2015, 17, 3202.

    Article  CAS  PubMed  Google Scholar 

  10. Pan G., Su L., Zhang Y., Guo S., Wang Y., RSC Adv., 2016, 6, 25375.

    Article  CAS  Google Scholar 

  11. Kundu N. G., Mahanty J. S., Das P., Das B., Tetrahedron Lett., 1993, 34, 1625.

    Article  CAS  Google Scholar 

  12. Paquette L. A., Poupart M. A., J. Org. Chem., 1993, 58, 4245.

    Article  CAS  Google Scholar 

  13. Sarvary I., Almqvist F., Frejd T., Chem. Eur. J., 2001, 7, 2158.

    Article  CAS  PubMed  Google Scholar 

  14. Kobayashi J. i., Kubota T., Nat. Prod. Rep., 2009, 26, 936.

    Article  CAS  PubMed  Google Scholar 

  15. Spangler J. E., Sorensen E. J., Tetrahedron, 2009, 65, 6739.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Weiss M. E., Carreira E. M., Angew. Chem. Int. Ed., 2011, 50, 11501.

    Article  CAS  Google Scholar 

  17. Liu M., Lin S., Gan M., Chen M., Li L., Wang S., Zi J., Fan X., Liu Y., Si Y., Yang Y., Chen X., Shi J., Org. Lett., 2012, 14, 1004.

    Article  CAS  PubMed  Google Scholar 

  18. Li Y., Wang J., Sun W., Shan Y., Sun B., Lin G., Zou J., Org. Chem. Frontiers, 2015, 2, 274.

    Article  Google Scholar 

  19. Cossu S., Battaggia S., De Lucchi O., J. Org. Chem., 1997, 62, 4162.

    Article  CAS  Google Scholar 

  20. Wagaman M. W., Bellmann E., Cucullu M., Grubbs R. H., J.Org. Chem., 1997, 62, 9076.

    Article  CAS  Google Scholar 

  21. Nicolaou K. C., Snyder S. A., Montagnon T., Vassilikogiannakis G., Angew. Chem. Int. Ed., 2002, 41, 1668.

    Article  CAS  Google Scholar 

  22. Thornqvist V., Manner S., Wingstrand M., Frejd T., J. Org. Chem., 2005, 70, 8609.

    Article  CAS  PubMed  Google Scholar 

  23. Wessig P., Müller G., Chem. Rev., 2008, 108, 2051.

    Article  CAS  PubMed  Google Scholar 

  24. Gregoritza M., Brandl F. P., Eur. J. Pharm. Biopharm, 2015, 97, 438.

    Article  CAS  PubMed  Google Scholar 

  25. Heravi M. M., Ahmadi T., Ghavidel M., Heidari B., Hamidi H., RSC Adv., 2015, 5, 101999.

    Article  CAS  Google Scholar 

  26. Xu M. M., Cai Q., Chin. J. Org. Chem., 2022, 42, 698.

    Article  CAS  Google Scholar 

  27. Ali S., Israr M., Chem. Commun., 2022, 58, 9851.

    Article  CAS  Google Scholar 

  28. Ahmed N., van Lier J. E., Tetrahedron Lett., 2006, 47, 2725.

    Article  CAS  Google Scholar 

  29. Kumar K. H., Perumal P. T., Canadian J. Chem., 2006, 84, 1079.

    Article  CAS  Google Scholar 

  30. Ahmed N., van Lier J. E., Tetrahedron Lett., 2007, 48, 13.

    Article  CAS  Google Scholar 

  31. Climent M. J., Corma A., Iborra S., Martí L., ChemCatChem, 2016, 8, 1335.

    Article  CAS  Google Scholar 

  32. Weinstein R. D., Renslo A. R., Danheiser R. L., Tester J. W., J. Phys. Chem. B, 1999, 103, 2878.

    Article  CAS  Google Scholar 

  33. Gómez M. V., Cantín Á., Corma A., de la Hoz A., J. Mol. Catal. A: Chem., 2005, 240, 16.

    Article  Google Scholar 

  34. Chen H., Trewyn B. G., Wiench J. W., Pruski M., Lin V. S., Top. Catal., 2010, 53, 187.

    Article  CAS  Google Scholar 

  35. Minakata S., Nagamachi T., Nakayama K., Suzuki T., Tanaka T., Chem. Commun., 2011, 47, 6338.

    Article  CAS  Google Scholar 

  36. Engel T., Kickelbick G., Chem. Mater., 2013, 25, 149.

    Article  CAS  Google Scholar 

  37. Shaykhutdinova P., Oestreich M., Organometallics, 2016, 35, 2768.

    Article  CAS  Google Scholar 

  38. Xia D., Cheng T., Xiao W., Liu K., Wang Z., Liu G., Li H., Wang W., ChemCatChem, 2013, 5, 1784.

    Article  CAS  Google Scholar 

  39. Deng B., Xiao W., Li C., Zhou F., Xia X., Cheng T., Liu G., J. Catal., 2014, 320, 70.

    Article  CAS  Google Scholar 

  40. Xu X., Cheng T., Liu X., Xu J., Jin R., Liu G., ACS Catal., 2014, 4, 2137.

    Article  CAS  Google Scholar 

  41. Zhang D., Cheng T., Liu G., Appl. Catal. B, 2015, 174/175, 344.

    Article  Google Scholar 

  42. Zhou F., Hu X., Gao M., Cheng T., Liu G., Green Chem., 2016, 18, 5651.

    Article  CAS  Google Scholar 

  43. Armarego W. L. F., Chai C., In Purification of Laboratory Chemicals (Seventh Edition), Butterworth-Heinemann, Boston, 2013, 103.

    Book  Google Scholar 

  44. Fang X., Liu Z., Hsieh M.-F., Chen M., Liu P., Chen C., Zheng N., ACS Nano, 2012, 6, 4434.

    Article  CAS  PubMed  Google Scholar 

  45. Zhou X., Chen H., Zhu Y., Song Y., Chen Y., Wang Y., Gong Y., Zhang G., Shu Z., Cui X., Zhao J., Shi J., Chem. Eur. J., 2013, 19, 10017.

    Article  CAS  PubMed  Google Scholar 

  46. Lok B. M., Marcus B. K., Angell C. L., Zeolites, 1986, 6, 185.

    Article  CAS  Google Scholar 

  47. De K., Legros J., Crousse B., Bonnet-Delpon D., J. Org. Chem., 2009, 74, 6260.

    Article  CAS  PubMed  Google Scholar 

  48. Boncel S., Saletra K., Hefczyc B., Walczak K. Z., Beilstein J. Org. Chem., 2011, 7, 173.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. Desmet G. B., D’hooge D. R., Omurtag P. S., Espeel P., Marin G. B., Du Prez F. E., Reyniers M.-F., J. Org. Chem., 2016, 81, 12291.

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 21872095), the “111” Innovation and Talent Recruitment Base on Photochemical and Energy Materials, China (No. D18020), and the Project of Shanghai Engineering Research Center of Green Energy Chemical Engineering, China (No. 18DZ2254200).

Author information

Authors and Affiliations

  1. The Education Ministry Key Lab of Resource Chemistry, Joint International Research Laboratory of Resource Chemistry, Ministry of Education, Shanghai Key Laboratory of Rare Earth Functional Materials, College of Chemistry and Materials Science, Shanghai Normal University, Shanghai, 200234, P. R. China

    Baoyan Li, Jingjing Meng, Yingding Li, Tanyu Cheng & Guohua Liu

  2. Lianhe Chemical Technology Co., Ltd., Yancheng, 224631, P. R. China

    Lingxia Jiang

Authors
  1. Baoyan Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jingjing Meng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yingding Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lingxia Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tanyu Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Guohua Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Tanyu Cheng or Guohua Liu.

Ethics declarations

The authors declare no conflicts of interest.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Li, B., Meng, J., Li, Y. et al. Protonated Mesoporous Aluminosilica Nanospheres Boosting Aza-Michael Cyclization and Diels-Alder Reaction. Chem. Res. Chin. Univ. (2024). https://doi.org/10.1007/s40242-024-4033-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s40242-024-4033-5

Keywords

Search

Navigation