Skip to main content
SpringerLink
Log in

NaIO4-Mediated Oxidative Cleavage of C–N Bond of Aza-Bridged Pyridoazepines to γLactams

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

An efficient and convenient protocol for the synthesis of γlactams has been developed. The selective C–N bond cleavage of aza-bridged pyridoazepines in the presence of NaIO4 and acetic acid smoothly proceeded to give the desired γlactams in good yields. This strategy possesses several advantages such as operational simplicity, safety, and environmental friendliness and therefore constitutes a promising tool for the synthesis of biologically active compounds.

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

Fig. 1.
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Caruano, J., Muccioli, G.G., and Robiette, R., Org. Biomol. Chem., 2016, vol. 14, p. 10134. https://doi.org/10.1039/C6OB01349J

    Article  CAS  Google Scholar 

  2. Piotrowska, D.G., Glowacka, I.E., Schols, D., Snoeck, R., Andrei, G., and Gotkowska, J., Molecules, 2019, vol. 24, article no. 4014. https://doi.org/10.3390/molecules24224014

  3. Song, D., Cao, X., Wang, J., and Ke, S., Bioorg. Med. Chem. Lett., 2020, vol. 30, article ID 126826. https://doi.org/10.1016/j.bmcl.2019.126826

  4. Huang, D., Wang, S., Song, D., Cao, X., Huang, W., and Ke, S., J. Agric. Food. Chem., 2020, vol. 68, p. 14438. https://doi.org/10.1021/acs.jafc.0c05823

    Article  CAS  Google Scholar 

  5. Yin, X., Ma, K., Dong, Y., and Dai, M., Org. Lett., 2020, vol. 22, p. 5001. https://doi.org/10.1021/acs.orglett.0c01570

    Article  CAS  Google Scholar 

  6. Liang, Z., Lin, Y.C., and Pierce, J.G., Org. Lett., 2021, vol. 23, p. 9559. https://doi.org/10.1021/acs.orglett.1c03782

    Article  CAS  Google Scholar 

  7. Rodgers, G., Wilson, E.J., Robertson, C.C., Cox, D.J., and Partridge, B.M., Adv. Synth. Catal., 2021, vol. 363, p. 2392. https://doi.org/10.1002/adsc.202001339

    Article  CAS  Google Scholar 

  8. Tan, D.Q., Atherton, A.L., Smith, A.J., Soldi, C., Hurley, K.A., Fettinger, J.C., and Shaw, J.T., ACS Comb. Sci., 2012, vol. 14, p. 218. https://doi.org/10.1021/co2001873

    Article  CAS  Google Scholar 

  9. Panger, J.L. and Denmark, S.E., Org. Lett., 2020, vol. 22, p. 2501. https://doi.org/10.1021/acs.orglett.9b04347

    Article  CAS  Google Scholar 

  10. Lorenc, C., Vibbert, H.B., Yao, C., Norton, J.R., and Rauch, M., ACS Catal., 2019, vol. 9, p. 10294. https://doi.org/10.1021/acscatal.9b03678

    Article  CAS  Google Scholar 

  11. Popescu, M.V., Mekereeya, A., Alegre-Requena, J.V., Paton, R.S., and Smith, M.D., Angew. Chem., Int. Ed., 2020, vol. 59, p. 23020. https://doi.org/10.1002/anie.202009704

    Article  CAS  Google Scholar 

  12. Jung, H., Keum, H., Kweon, J., and Chang, S., J. Am. Chem. Soc., 2020, vol. 142, p. 5811. https://doi.org/10.1021/jacs.0c00868

    Article  CAS  Google Scholar 

  13. Tan, T.-D. and Ye, L.-W., Nat. Catal., 2019, vol. 2, p. 182. https://doi.org/10.1038/s41929-019-0236-4

    Article  CAS  Google Scholar 

  14. Ganesh Kumar, M., Veeresh, K., Nalawade, S.A., Nithun, R.V., and Gopi, H.N., J. Org. Chem., 2019, vol. 84, p. 15145. https://doi.org/10.1021/acs.joc.9b01936

    Article  CAS  Google Scholar 

  15. Ye, Z.P., Xia, P.J., Liu, F., Hu, Y.Z., Song, D., Xiao, J.A., Huang, P., Xiang, H.Y., Chen, X.Q., and Yang, H., J. Org. Chem., 2020, vol. 85, p. 5670. https://doi.org/10.1021/acs.joc.9b03490

    Article  CAS  Google Scholar 

  16. Del Corte, X., López-Francés, A., Maestro, A., Martinez de Marigorta, E., Palacios, F., and Vicario, J., J. Org. Chem., 2020, vol. 85, p. 14369. https://doi.org/10.1021/acs.joc.0c00280

    Article  CAS  Google Scholar 

  17. Brandão, P., López, Ó., Leitzbach, L., Stark, H., Fernández-Bolaños, J.G., Burke, A.J., and Pineiro, M., ACS Med. Chem. Lett., 2021, vol. 12, p. 1718. https://doi.org/10.1021/acsmedchemlett.1c00344

    Article  CAS  Google Scholar 

  18. Jung, H.Y., Chang, S., and Hong, S., Org. Lett., 2019, vol. 21, p. 7099. https://doi.org/10.1021/acs.orglett.9b02673

    Article  CAS  Google Scholar 

  19. Fujii, T., Thu, H.D.T., and Iwasa, S., Tetrahedron Lett., 2020, vol. 61, article ID 152276. https://doi.org/10.1016/j.tetlet.2020.152276

  20. Shao, N.Q., Chen, Y.H., Li, C., and Wang, D.H., Org. Lett., 2020, vol. 22, p. 7141. https://doi.org/10.1021/acs.orglett.0c00326

    Article  CAS  Google Scholar 

  21. Torelli, A., Whyte, A., Polishchuk, I., Bajohr, J., and Lautens, M., Org. Lett., 2020, vol. 22, p. 7915. https://doi.org/10.1021/acs.orglett.0c02837

    Article  CAS  Google Scholar 

  22. Wu, L.S., Ding, Y., Han, Y.Q., and Shi, B.F., Org. Lett., 2021, vol. 23, p. 2048. https://doi.org/10.1021/acs.orglett.1c00204

    Article  CAS  Google Scholar 

  23. Chen, J.Q., Chang, R., Lin, J.B., Luo, Y.C., and Xu, P.F., Org. Lett., 2018, vol. 20, p. 2395. https://doi.org/10.1021/acs.orglett.8b00731

    Article  CAS  Google Scholar 

  24. Zhang, Y., Zhu, Y., Zheng, L., Zhuo, L.G., Yang, F., Dang, Q., Yu, Z.X., and Bai, X., Eur. J. Org. Chem., 2014, vol. 2014, p. 660. https://doi.org/10.1002/ejoc.201301318

    Article  CAS  Google Scholar 

  25. Zhang, Y., Yang, F., Zheng, L., Dang, Q. and Bai, X., Org. Lett., 2014, vol. 16, p. 6041. https://doi.org/10.1021/ol502971e

    Article  CAS  Google Scholar 

  26. Zhang, Y., Zheng, L., Yang, F., Zhang, Z., Dang, Q., and Bai, X., Tetrahedron, 2015, vol. 71, p. 1930. https://doi.org/10.1016/j.tet.2015.02.025

    Article  CAS  Google Scholar 

  27. Zhang, Y., Bao, Q., Zhang, N., Wang, S., and Yu, X., RSC Adv., 2020, vol. 10, p. 41802. https://doi.org/10.1039/D0RA08758K

    Article  CAS  Google Scholar 

  28. Dairo, T.O., Nelson, N.C., Slowing, I.I., Angelici, R.J., and Woo, L.K., Catal. Lett., 2016, vol. 146, p. 2278. https://doi.org/10.1007/s10562-016-1834-2

    Article  CAS  Google Scholar 

  29. Khusnutdinova, J.R., Ben-David, Y., and Milstein, D., J. Am. Chem. Soc., 2014, vol. 136, p. 2998. https://doi.org/10.1021/ja500026m

    Article  CAS  Google Scholar 

  30. Jin, X., Kataoka, K., Yatabe, T., Yamaguchi, K., and Mizuno, N., Angew. Chem., Int. Ed., 2016, vol. 55, p. 7212. https://doi.org/10.1002/anie.201602695

    Article  CAS  Google Scholar 

  31. Dai, F., Yang, Y., Gu, J., Fang, Z., Yang, Z., Liu, C., He, W., Zhu, N., Lu, B., and Guo, K., ChemistrySelect, 2019, vol. 4, p. 3500. https://doi.org/10.1002/slct.201900090

    Article  CAS  Google Scholar 

  32. Yuan, D., Tian, L., Li, Z., Jiang, H., Yan, C., Dong, J., Wu, H., and Wang, B., Sci. Rep., 2018, vol. 8, p. 3103. https://doi.org/10.1038/s41598-018-21473-z

    Article  CAS  Google Scholar 

  33. Ravi, K., Bankar, B.D., Jindani, S., and Biradar, A.V., ACS Omega, 2019, vol. 4, p. 9453. https://doi.org/10.1021/acsomega.9b00543

    Article  CAS  Google Scholar 

  34. Ali Shaikh, T.M., Emmanuvel, L., and Sudalai, A., J. Org. Chem., 2006, vol. 71, p. 5043. https://doi.org/10.1021/jo0606305

    Article  CAS  Google Scholar 

  35. Richers, M.T., Zhao, C., and Seidel, D., Beilstein J. Org. Chem., 2013, vol. 9, p. 1194. https://doi.org/10.3762/bjoc.9.135

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors acknowledge the assistance of JLICT Center of Characterization and Analysis.

Funding

This study was performed under financial support by the Science and Technology Project of Jilin Provincial Department of Education (JJKH20200242KJ), Science and Technology Innovation and Development Plan Project in Jilin City (20190104196), and Research projects in Jilin Institute of Chemical Technology (2016004, 2018030).

Author information

Authors and Affiliations

  1. School of Chemistry and Pharmaceutical Engineering, Jilin Institute of Chemical Technology, 132022, Jilin, China

    Y. W. Zhang, Y. L. Jia, D. Wang, L. Q. Cheng & X. Yu

  2. Forensic Center of Changchun Public Security Bureau, 130000, Changchun, China

    J. Chen

  3. Organic Synthesis Plant of PetroChina, Jilin Petrochemical Company, 132022, Jilin, China

    F. L. Liu

Authors
  1. Y. W. Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Y. L. Jia
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. J. Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. F. L. Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. L. Q. Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. X. Yu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to X. Yu.

Ethics declarations

The authors declare no conflict of interest.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, Y.W., Jia, Y.L., Wang, D. et al. NaIO4-Mediated Oxidative Cleavage of C–N Bond of Aza-Bridged Pyridoazepines to γLactams. Russ J Org Chem 58, 1474–1480 (2022). https://doi.org/10.1134/S107042802210013X

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042802210013X

Keywords:

Search

Navigation