Skip to main content
SpringerLink
Log in

Mannich Reaction in the Synthesis of Azaperoxides

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

Abstract

New tetraoxaazadispiroalkanes have been synthesized by the three-component Mannich reaction of primary aromatic amines with geminal bis-hydroperoxides and cyclohexanone using Sm(NO3)3·6H2O as catalyst.

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

Scheme

Similar content being viewed by others

REFERENCES

  1. Amewu, R.K., Chadwick, J., Hussain, A., Panda, S., Rinki, R., Janneh, O., Ward, S.A., Miguel, C., Burrell-Saward, H., Vivas, L., and O’Neill, P.M., Bioorg. Med. Chem., 2013, vol. 21, p. 7392. https://doi.org/10.1016/j.bmc.2013.09.047

    Article  CAS  Google Scholar 

  2. Tang, Y., Dong, Y., Karle, J.M., DiTusa, C.A., and Vennerstrom, J.L., J. Org. Chem., 2004, vol. 69, p. 6470. https://doi.org/10.1021/jo040171c

    Article  CAS  Google Scholar 

  3. Dong, Y., Chollet, J., Matile, H., Charman, S.A., Chiu, F.C.K., Charman, W.N., Scorneaux, B., Urwyler, H., Tomas, J.S., Scheurer, C., Snyder, C., Dorn, A., Wang, X., Karle, J.M., Tang, Y., Wittlin, S., Brun, R., and Vennerstrom, J.L., J. Med. Chem., 2005, vol. 48, p. 4953. https://doi.org/10.1021/jm049040u

    Article  CAS  Google Scholar 

  4. Dong, Y., Tang, Y., Chollet, J., Matile, H., Wittlin, S., Charman, S.A., Charman, W.N., Tomas, J.S., Scheurer, C., Snyder, C., Scorneaux, B., Bajpai, S., Alexander, S.A., Wang, X., Padmanilayam, M., Cheruku, S.R., Brun, R., and Vennerstrom, J.L., Bioorg. Med. Chem., 2006, vol. 14, p. 6368. https://doi.org/10.1016/j.bmc.2006.05.041

    Article  CAS  Google Scholar 

  5. Tang, Y., Dong, Y., Wittlin, S., Charman, S.A., Chollet, J., Chiu, F.C.K., Charman, W.N., Matile, H., Urwyler, H., Dorn, A., Bajpai, S., Wang, X., Padmanilayam, M., Karle, J.M., Brun, R., and Venner­strom, J.L., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 1260. https://doi.org/10.1016/j.bmcl.2006.12.007

    Article  CAS  Google Scholar 

  6. Slack, R., Jacobine, A., and Posner, G., MedChemComm, 2012, vol. 3, p. 281. https://doi.org/10.1039/C2MD00277A

    Article  CAS  Google Scholar 

  7. Vil’, V., Yaremenko, I., Ilovaisky, A., and Terent’ev, A., Molecules, 2017, vol. 22, article no. 1881. https://doi.org/10.3390/molecules22111881

  8. Liu, D.-Z. and Liu, J.-K., Nat. Prod. Bioprospect., 2013, vol. 3, p. 161. https://doi.org/10.1007/s13659-013-0042-7

    Article  CAS  Google Scholar 

  9. Kawamura, Y., Takayama, R., Nishiuchi, M., and Tsuka­yama, M., Tetrahedron Lett., 2000, vol. 41, p. 8101. https://doi.org/10.1016/S0040-4039(00)01412-X

    Article  CAS  Google Scholar 

  10. White, E.H., Li, M., and Roswell, D.F., Photochem. Photobiol., 1991, vol. 53, p. 125. https://doi.org/10.1111/j.1751-1097.1991.tb08477.x

    Article  CAS  Google Scholar 

  11. Kraljic, I. and El Mohsni, S., Photochem. Photobiol., 1978, vol. 28, p. 577. https://doi.org/10.1111/j.1751-1097.1978.tb06972.x

    Article  CAS  Google Scholar 

  12. Vennerstrom, J.L., J. Med. Chem., 1989, vol. 32, no. 1, p. 64. https://doi.org/10.1021/jm00121a013

    Article  CAS  Google Scholar 

  13. Sundar, N., Jacob, V.T., Bhat, S.V., Valecha, N., and Biswas, S., Bioorg. Med. Chem. Lett., 2001, vol. 11, p. 2269. https://doi.org/10.1016/S0960-894X(01)00396-1

    Article  CAS  Google Scholar 

  14. Makhmudiyarova, N.N., Rakhimov, R.Sh., Tyumki­na, T.V., Meshcheryakova, E.S., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2019, vol. 55, no. 5, p. 713. https://doi.org/10.1134/s1070428019050075

    Article  CAS  Google Scholar 

  15. Makhmudiyarova, N.N., Ishmukhametova, I.R., Dzhemileva, L.U., Tyumkina, T.V., D’yakonov, V.A., Ibragimov, A.G., and Dzhemilev, U.M., RSC Adv., 2019, vol. 9, p. 18923. https://doi.org/10.1039/c9ra02950h

    Article  CAS  Google Scholar 

  16. Makhmudiyarova, N.N., Ishmukhametova, I.R., Dzhemileva, L.U., D’yakonov, V.A., Ibragimov, A.G., and Dzhemilev, U.M., Molecules, 2020, vol. 25, article no. 1874. https://doi.org/10.3390/molecules25081874

  17. Makhmudiyarova, N.N., Ishmukhametova, I.R., Dzhe­mi­leva, L.U., D’yakonov, V.A., Ibragimov, A.G., and Dzhemilev, U.M., Russ. J. Org. Chem., 2020, vol. 56, p. 746. https://doi.org/10.1134/s1070428020050115

    Article  CAS  Google Scholar 

  18. Makhmudiyarova, N.N., Ishmukhametova, I.R., Shan­garaev, K.R., Dzhemileva, L.U., D’yakonov, V.A., Ibragimov, A.G., and Dzhemilev, U.M., New J. Chem., 2021, vol. 45, p. 2069. https://doi.org/10.1039/d0nj05511e

    Article  CAS  Google Scholar 

  19. Terent’ev, A.O., Platonov, M.M., Ogibin, Y.N., and Nikishin, G.I., Synth. Commun., 2007, vol. 37, p. 1281. https://doi.org/10.1080/00397910701226384

    Article  CAS  Google Scholar 

Download references

Funding

This study was financially supported in the framework of state assignment to the Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences (project no. FMRS-2022-0079).

Author information

Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences, 450075, Ufa, Russia

    N. N. Makhmudiyarova & I. R. Ishmukhametova

Authors
  1. N. N. Makhmudiyarova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. R. Ishmukhametova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. N. Makhmudiyarova.

Ethics declarations

The authors declare the absence of conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Makhmudiyarova, N.N., Ishmukhametova, I.R. Mannich Reaction in the Synthesis of Azaperoxides. Russ J Org Chem 58, 1950–1953 (2022). https://doi.org/10.1134/S1070428022120247

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022120247

Keywords:

Search

Navigation