Skip to main content
SpringerLink
Log in

Three-Step Synthesis of 2-Acetyl-4-methyl-3,4-dihydropyran Oximes from Acetylbenzenes and Acetylene

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

Abstract

2-Acetyl-4-methyl-3,4-dihydropyrans reacted with hydroxylamine in pyridine to give (E)-1-(4-methyl-3,4-dihydro-2H-pyran-2-yl)ethan-1-one oximes in up to 85% yield with high stereoselectivity.

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. Mikhaleva, A.I., Zaitsev, A.B., and Trofimov, B.A., Russ. Chem. Rev., 2006, vol. 75, no. 9, p. 797.

    Article  CAS  Google Scholar 

  2. Rubina, K., Abele, E., Belyakov, S., Shestakova, I., and Popelis, Yu., Russ. J. Org. Chem., 2006, vol. 42, no. 5, p. 735.

    Article  CAS  Google Scholar 

  3. Kukharev, B.F., Stankevich, V.K., Klimenko, G.R., and Shaposhnikova, A.N., Russ. J. Org. Chem., 2007, vol. 43, no. 2, p. 181.

    Article  CAS  Google Scholar 

  4. Zhukovskaya, N.A. and Dikusar, E.A., Russ. J. Org. Chem., 2010, vol. 46, no. 2, p. 180.

    Article  CAS  Google Scholar 

  5. Trofimov, B.A. and Mikhaleva, A.I., Russ. J. Org. Chem., 1996, vol. 32, no. 8, p. 1083.

    Google Scholar 

  6. Korostova, S.E., Mikhaleva, A.I., Vasil’tsov, A.M., and Trofimov, B.A., Russ. J. Org. Chem., 1998, vol. 34, no. 12, p. 1691.

    CAS  Google Scholar 

  7. Zaitsev, A.B., Vasil’tsov, A.M., Shmidt, E.Yu., Mikhaleva, A.I., Afonin, A.V., and Il’icheva, L.N., Russ. J. Org. Chem., 2003, vol. 39, no. 10, p. 1406.

    Article  CAS  Google Scholar 

  8. Mikhaleva, A.I., Shmidt, E.Yu., Ivanov, A.V., Vasil’-tsov, A.M., Senotrusova, E.Yu., and Protsuk, N.I., Russ. J. Org. Chem., 2007, vol. 43, no. 2, p. 228.

    Article  CAS  Google Scholar 

  9. Ngwerume, S. and Camp, J.E., Chem. Commun., 2011, vol. 47, p. 1857.

    Article  CAS  Google Scholar 

  10. Trofimov, B.A., Mikhaleva, A.I., Shmidt, E.Yu., and Sobenina, L.N., Chemistry of Pyrroles, Boca Raton: CRC, 2015.

    Google Scholar 

  11. Schmidt, E.Yu., Trofimov, B.A., Mikhaleva, A.I., Zorina, N.V., Protzuk, N.I., Petrushenko, K.B., Ushakov, I.A., Dvorko, M.Yu., Méallet-Renault, R., Clavier, G., Vu, T.T., Tran, H.T., and Pansu, R.B., Chem. Eur. J., 2009, vol. 15, no. 23, p. 5823.

    Article  CAS  PubMed  Google Scholar 

  12. Trofimov, B.A. and Schmidt, E.Yu., Russ. Chem. Rev., 2014, vol. 83, no. 7, p. 600.

    Article  CAS  Google Scholar 

  13. Domino Reactions, Tietze, L.F., Ed., Weinheim: Wiley-VCH, 2014.

    Google Scholar 

  14. Pirnot, M.T., Wang, Y.-M., and Buchwald, S.L., Angew. Chem., Int. Ed., 2016, vol. 55, no. 1, p. 48.

    Article  CAS  Google Scholar 

  15. Galkin, K.I. and Ananikov, V.P., Russ. Chem. Rev., 2016, vol. 85, no. 3, p. 226.

    Article  CAS  Google Scholar 

  16. Alyabyev, S.B. and Beletskaya, I.P., Russ. Chem. Rev., 2017, vol. 86, no. 8, p. 689.

    Article  CAS  Google Scholar 

  17. Clarke, P.A., Santos, S., and Martin, W.H.C., Green Chem., 2007, vol. 9, p. 438.

    Article  CAS  Google Scholar 

  18. Xiang, H., Chen, Y., He, Q., Xie, Y., and Yang, C., RSC Adv., 2013, vol. 3, p. 5807.

    Article  CAS  Google Scholar 

  19. Vereshchagin, A.N., Elinson, M.N., Anisina, Yu.E., Ryzhkov, F.V., Goloveshkin, A.S., Bushmarinov, I.S., Zlotin, S.G., and Egorov, M.P., Mendeleev Commun., 2015, vol. 25, p. 424.

    Article  CAS  Google Scholar 

  20. Trofimov, B.A., Schmidt, E.Yu., Ushakov, I.A., Mikhaleva, A.I., Zorina, N.V., Protsuk, N.I., Senotrusova, E.Yu., Skital’tseva, E.V., Kazheva, O.N., Alexandrov, G.G., and Dyachenko, O.A., Eur. J. Org. Chem., 2009, p. 5142.

    Google Scholar 

  21. Schmidt, E.Yu., Trofimov, B.A., Zorina, N.V., Mikhaleva, A.I., Ushakov, I.A., Skital’tseva, E.V., Kazheva, O.N., Alexandrov, G.G., and Dyachenko, O.A., Eur. J. Org. Chem., 2010, p. 6727.

    Google Scholar 

  22. Dabbagh, H.A. and Teimouri, A., Russ. J. Org. Chem., 2008, vol. 44, no. 10, p. 1464.

    Article  CAS  Google Scholar 

  23. Gevorkyan, A.A., Arakelyan, A.S., Barsegyan, S.V., Petrosyan, K.A., and Panosyan, G.A., Russ. J. Org. Chem., 2003, vol. 39, no. 8, p. 1204.

    Article  CAS  Google Scholar 

  24. Kocak, A., Malkondu, S., and Kurbanli, S., Russ. J. Org. Chem., 2009, vol. 45, no. 4, p. 591.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    I. V. Tatarinova, N. I. Protsuk, I. A. Ushakov, E. Yu. Schmidt & B. A. Trofimov

Authors
  1. I. V. Tatarinova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. I. Protsuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. A. Ushakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. Yu. Schmidt
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. B. A. Trofimov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to B. A. Trofimov.

Additional information

Original Russian Text © I.V. Tatarinova, N.I. Protsuk, I.A. Ushakov, E.Yu. Schmidt, B.A. Trofimov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 4, pp. 654–656.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tatarinova, I.V., Protsuk, N.I., Ushakov, I.A. et al. Three-Step Synthesis of 2-Acetyl-4-methyl-3,4-dihydropyran Oximes from Acetylbenzenes and Acetylene. Russ J Org Chem 54, 659–661 (2018). https://doi.org/10.1134/S1070428018040255

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018040255

Search

Navigation