Skip to main content
SpringerLink
Log in

One-pot synthesis of 1,5-benzodiazepine-2,3-dicarboxylates via three-component domino reactions in the presence of γ-Fe2O3@SiO2/Ce(OTf)3

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Novel, efficient and environmentally friendly approaches have been developed for the synthesis of 1,5-benzodiazepine-2,3-dicarboxylates by one-pot three-component domino reactions in the presence of a catalytic amount of γ-Fe2O3@SiO2/Ce(OTf)3 in EtOH at ambient temperature. A total of 32 2,5-dihydro-1H-1,5-benzodiazepine-2,3-dicarboxylates and 2-methyl-2,3-dihydro-1H-1,5-benzodiazepine-2,3-dicarboxylates with enamine or imine structure of the heterocycle, respectively, were obtained in good yields by reacting substituted 1,2-phenylenediamine, β-carbonyl esters, and ethyl glyoxylate or ethyl pyruvate. One-pot reactions were successfully realized to form one new cycle and four new bonds (one C–C, two C–N, one C=C or two C–C, one C–N, one C=N). Furthermore, plausible mechanisms for the formation of 1,5-benzodiazepine-2,3-dicarboxylates have been proposed. The salient features of this reaction include short reaction time, mild reaction conditions, moderate to excellent yields, recyclability of the catalyst, and wide substrate scope.

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

Figure 1.
Scheme 1.
Scheme 2.
Scheme 3.
Figure 2.
Figure 3.
Figure 4.
Scheme 4.
Figure 5.

Similar content being viewed by others

References

  1. Ye, P.; Shao, Y.; Ye, X.; Zhang, F.; Li, R.; Sun, J.; Xu, B.; Chen, J. Org. Lett. 2020, 22, 1306.

    Article  CAS  Google Scholar 

  2. Yao, X.; Shao, Y.; Hu, M.; Xia, Y.; Cheng, T.; Chen, J. Org. Lett. 2019, 21, 7697.

    Article  CAS  Google Scholar 

  3. Yao, X.; Shao, Y.; Hu, M.; Zhang, M.; Li, S.; Xia, Y.; Cheng, T.; Chen, J. Adv. Synth. Catal. 2019, 361, 4707.

    Article  CAS  Google Scholar 

  4. Das, B. G.; Shah, S.; Singh, V. K. Org. Lett. 2019, 21, 4981.

    Article  CAS  Google Scholar 

  5. Xiong, W.; Hu, K.; Lei, Y.; Zhen, Q.; Zhao, Z.; Shao, Y.; Li, R.; Zhang, Y.; Chen, J. Org. Lett. 2020, 22, 1239.

    Article  CAS  Google Scholar 

  6. Hu, K.; Zhen, Q.; Gong, J.; Cheng, T.; Qi, L.; Shao, Y.; Chen, J. Org. Lett. 2018, 20, 3083.

    Article  CAS  Google Scholar 

  7. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfeld, J. J. Med. Chem. 1988, 31, 2235.

    Article  CAS  Google Scholar 

  8. Hada, E. M.; Dawson, E. S.; Darrow, J. W.; Sugg, E. E.; Lybrand, T. P.; Miller, L. J. J. Med. Chem. 2006, 49, 850.

    Article  Google Scholar 

  9. Prevot, T. D.; Li, G.; Vidojevic, A.; Misquitta, K. A.; Fee, C.; Santrac, A.; Knutson, D. E.; Stephen, M. R.; Kodali, R.; Zahn, N. M.; Arnold, L. A.; Scholze, P.; Fisher, J. L.; Marković, B. D.; Banasr, M.; Cook, J. M.; Savic, M.; Sibille, E. Mol. Neuropsychiatry 2019, 5, 84.

    Article  CAS  Google Scholar 

  10. Romal, G.; Grossi, G. C.; Braccio, M. D.; Ghia, M.; Mattioli, F. Eur. J. Med. Chem. 1991, 26, 489.

    Article  Google Scholar 

  11. Eleftheriadis, N.; Neochoritis, C. G.; Tsoleridis, C. A.; Stephanidou-Stephanatou, J.; Iakovidou-Kritsi, Z. Eur. J. Med. Chem. 2013, 67, 302.

    Article  CAS  Google Scholar 

  12. Ochoa, J. G.; Kilgo, W. A. Curr. Treat. Options Neurol. 2016, 18, 18.

    Article  Google Scholar 

  13. Misra, A.; Jain, S.; Kishore, D.; Dave, V.; Reddy, K. R.; Sadhu, V.; Dwivedi, J.; Sharma, S. J. Microbiol. Methods 2019, 163, 105648.

    Article  Google Scholar 

  14. Grossi, G.; Braccio, M. D.; Roma, G.; Ballabeni, V.; Tognolini, M.; Calcina, F.; Barocelli, E. Eur. J. Med. Chem. 2002, 37, 933.

    Article  CAS  Google Scholar 

  15. Leyva-Pérez, A.; Cabrero-Antonino, J. R.; Corma, A. Tetrahedron 2010, 66, 8203.

    Article  Google Scholar 

  16. Misra, A.; Kishore, D.; Verma, V. P.; Dubey, S.; Chander, S.; Gupta, N.; Bhagyawant, S.; Dwivedi, J.; Alothman, Z. A.; Wabaidur, S. M.; Sharma, S. J. King Saud Univ., Sci. 2020, 32, 1486.

  17. Carter, M. C.; Alber, D. G.; Baxter, R. C.; Bithell, S. K.; Budworth, J.; Chubb, A.; Cockerill, G. S.; Dowdell, V. C. L.; Henderson, E. A.; Keegan, S. J.; Kelsey, R. D.; Lockyer, M. J.; Stables, J. N.; Wilson, L. J.; Powell, K. L. J. Med. Chem. 2006, 49, 2311.

    Article  CAS  Google Scholar 

  18. Balon, R.; Rafanelli, C.; Sonino, N. Psychother. Psychosom. 2018, 87, 327.

    Article  Google Scholar 

  19. Wang, L. Z.; Li, X. Q.; An, Y. S. Org. Biomol. Chem. 2015, 13, 5497.

    Article  CAS  Google Scholar 

  20. Ghorbani-Vaghei, R.; Veisi, H. Mol. Diversity 2010, 14, 249.

    Article  CAS  Google Scholar 

  21. Wu, Y. Y.; Tian, K. Q.; Yang, T.; Du, X. Q.; Zhang, P. Chin. J. Org. Chem. 2013, 33, 1465.

    Article  CAS  Google Scholar 

  22. An, Y. S.; Hao, Z. F.; Zhang, X. J.; Wang, L. Z. Chem. Biol. Drug Des. 2016, 88, 110.

    Article  CAS  Google Scholar 

  23. Sun, Y. W.; Wang, L. Z. New J. Chem. 2018, 42, 20032.

    CAS  Google Scholar 

  24. Sun, Y. W.; Bei, Y. M.; Wang, L. Z. Org. Biomol. Chem. 2019, 17, 930.

    Article  CAS  Google Scholar 

  25. Zhou, L. Y.; Wang, M. L.; Wang, K. X.; Wen, T. T.; Wang, L. Z. Appl. Organomet. Chem. 2020, 34, e5707.

  26. Barrett, E. P.; Joyner, L. G.; Halenda, P. P. J. Am. Chem. Soc. 1951, 73, 373.

    Article  CAS  Google Scholar 

  27. Chen, D. B.; Bao, W. L. Adv. Synth. Catal. 2010, 352, 955.

    Article  CAS  Google Scholar 

  28. Sheldrick, G. M.; Schneider, T. R. Methods Enzymol. 1997, 277, 319.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Hebei Key Laboratory of Organic Functional Molecules, College of Chemistry and Materials Science, Hebei Normal University, Shijiazhuang, 050024, China

    Xiaoying An, Lei Gao, Mingliang Wang, Haitao Wu & Lanzhi Wang

Authors
  1. Xiaoying An
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lei Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mingliang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Haitao Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Lanzhi Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lanzhi Wang.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 806–816

Supplementary Information

ESM 1

(PDF 5470 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

An, X., Gao, L., Wang, M. et al. One-pot synthesis of 1,5-benzodiazepine-2,3-dicarboxylates via three-component domino reactions in the presence of γ-Fe2O3@SiO2/Ce(OTf)3. Chem Heterocycl Comp 57, 806–816 (2021). https://doi.org/10.1007/s10593-021-02984-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02984-6

Keywords

Search

Navigation