Skip to main content
SpringerLink
Log in

One-Pot Synthesis of 2,3,4,4a,10,10a-Hexahydro-1H-phenoxazines

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

Abstract

A procedure has been proposed for the synthesis of 2,3,4,4a,10,10a-hexahydro-1H-phenoxazines by reductive cyclization of 2-(2-nitrophenoxy)cyclohexan-1-ones over palladium catalysts under mild conditions (ethanol, 318 K, pH 2 = 0.1 MPa). The product structure and ratio were determined by 1H and 13C NMR spectra, X-ray analysis, and GC/MS data. The reductive cyclization of 2-(2-nitrophenoxy)cyclohexan-1-one and 2-(4-methyl-2-nitrophenoxy)cyclohexan-1-one has been shown to produce 2,3,4,4a,10,10a-hexahydro-1H-phenoxazine and its 8-methyl analog as mixtures of stereoisomers with trans and cis-junction of the cyclo-hexane and morpholine rings at ratios of 1:3 and 3:1, respectively.

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. Albanese, D., Landini, D., Lupi, V., and Penso, M., Ind. Eng. Chem. Res., 2003, vol. 42, p. 680. doi 10.1021/ ie020702

    Article  CAS  Google Scholar 

  2. Rao, R.K., Naidu, A.B., and Sekar, G., Org. Lett., 2009, vol. 11, p. 1923. doi 10.1021/ol9003299

    Article  CAS  Google Scholar 

  3. Liu, Z. and Chen, Y., Tetrahedron Lett., 2009, vol. 50, p. 3790. doi 10.1016/j.tetlet.2009.04.055

    Article  CAS  Google Scholar 

  4. Liu, T., Jia, W., Xi, Q., Chen, Y., Wang, X., and Yin, D., J. Org. Chem., 2018, vol. 83, p. 1387. doi 10.1021/ acs.joc.7b02894

    Article  CAS  Google Scholar 

  5. Brown, D.W., Ninan, A., and Sainsbury, M., Synthesis, 1997, p. 895. doi 10.1055/s-1997-1290

    Google Scholar 

  6. Wei, S., Feng, X., and Du, H., Org. Biomol. Chem., 2016, vol. 14, p. 8026. doi 10.1039/C6OB01556E

    Article  CAS  Google Scholar 

  7. Qin, J., Chen, F., He, Y.-M., and Fan, Q.-H., Org. Chem. Front., 2014, vol. 1, p. 952. doi 10.1039/c4qo00188e

    Article  CAS  Google Scholar 

  8. Gao, K., Yu, C.-B., Wang, D.-S., and Zhou, Y.-G., Adv. Synth. Catal., 2012, vol. 354, p. 483. doi 10.1002/ adsc.201100568

    Article  CAS  Google Scholar 

  9. Aillerie, A., Gosset, C., Dumont, C., Skrzypczak, V., Champetter, P., Pellegrini, S., Bousquet, T., and Pélinski, L., RSC Adv., 2016, vol. 6, p. 54185. doi 10.1039/C6RA04930C

    Article  CAS  Google Scholar 

  10. Zhang, Z., Ji, Y.R., Wojtas, L., Gao, W.-Y., Ma, S., Zaworotko, M.J., and Antilla, J.C., Chem. Commun., 2013, vol. 49, p. 7693. doi 10.1039/c3cc43801e

    Article  CAS  Google Scholar 

  11. Kundu, D.S., Schmidt, J., Bleschke, C., Thomas, A., and Blechert, S., Angew. Chem., Int. Ed., 2012, vol. 51, p. 5456. doi 10.1002/anie.201109072

    Article  CAS  Google Scholar 

  12. Baraldi, P.G., Saponaro, G., Moorman, A.R., Romagnoli, R., Preti, D., Baraldi, S., Ruggiero, E., Varani, K., Targa, M., Vincenzi, F., and Tabrizi, M.A., J. Med. Chem., 2012, vol. 55, p. 6608. doi 10.1021/ jm300763w

    Article  CAS  Google Scholar 

  13. Bunce, R.A., Herron, D.M., and Hale, L.Y., J. Heterocycl. Chem., 2003, vol. 40, p. 1031. doi 10.1002/jhet.5570400611

    Article  CAS  Google Scholar 

  14. Ye, F., Zhou, X.-L., Qu, H.-T., Yi, K.-H., and Fu, Y., J. Chem. Eng. Chin. Univ., 2015, vol. 29, p. 1525. doi 10.3969/j.issn.1003-9015.2015.06.035

    CAS  Google Scholar 

  15. Gao, S., Qu, H.-T., Ye, F., and Fu, Y., J. Chem., 2015, vol. 2015, article ID 268306. doi 10.1155/2015/268306

  16. Nishiwaki, N., Hisaki, M., Ono, M., and Ariga, M., Te trahedron, 2009, vol. 65, p. 7403. doi 10.1016/j.tet.2009.07.024

    Article  CAS  Google Scholar 

  17. Kalmykov, P.A., Magdalinova, N.A., and Klyuev, M.V., Pet. Chem., 2015, vol. 55, p. 63. doi 10.1134/S0965544115010065

    Article  CAS  Google Scholar 

  18. Kalmykov, P.A. and Klyuev, M.V., Pet. Chem., 2016, vol. 56, p. 27. doi 10.1134/S0965544115080095

    Article  CAS  Google Scholar 

  19. Kalmykov, P.A., Magdalinova, N.A., and Klyuev, M.V., Butlerov Commun., 2016, vol. 47, p. 1.

    Google Scholar 

  20. Krylov, O.V., Geterogennyi kataliz: Uchebnoe posobie dlya vuzov (Heterogeneous Catalysis. Textbook for Higher School), Moscow: Akademkniga, 2004.

    Google Scholar 

  21. Macrae, C.F., Bruno, I.J., Chisholm, J.A., Edging-ton, P.R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J., and Wood, P.A., J. Appl. Crystallogr., 2008, vol. 41, p. 466. doi 10.1107/ S0021889807067908

    Article  CAS  Google Scholar 

  22. Spek, A.L., Acta Crystallogr., Sect. D, 2009, vol. 65, p. 148. doi 10.1107/S090744490804362X

    Article  CAS  Google Scholar 

  23. Shapenova, D.S. and Belyatskii, M.K., Vestn. Tyumen. Gos. Univ., 2011, p. 119.

    Google Scholar 

  24. Liu, T., Jia, W., Xi, Q., Chen, Y., Wang, X., and Yin, D., J. Org. Chem., 2018, vol. 83, p. 1387. doi 10.1021/ acs.joc.7b02894

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Gas chromatographic-mass spectrometric analyses were performed at the “Rational Nature Management and Physicochemical Studies” joint center at the Institute of Chemistry, Tyumen State University.

Funding

This study was performed under financial support by the M. Prokhorov Foundation in the framework of the “Academic Mobility” program (agreement no. AM-51/17).

Author information

Authors and Affiliations

  1. Tumen State University, Tumen, Russia

    D. S. Shapenova

  2. Ivanovo State University, Ivanovo, Russia

    N. A. Magdalinova & M. V. Klyuev

Authors
  1. D. S. Shapenova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. A. Magdalinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. V. Klyuev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to D. S. Shapenova or M. V. Klyuev.

Ethics declarations

The authors declare the absence of conflict of interests.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 9, pp. 1388–1392.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shapenova, D.S., Magdalinova, N.A. & Klyuev, M.V. One-Pot Synthesis of 2,3,4,4a,10,10a-Hexahydro-1H-phenoxazines. Russ J Org Chem 55, 1305–1309 (2019). https://doi.org/10.1134/S1070428019090070

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019090070

Keywords

Search

Navigation