Skip to main content
SpringerLink
Log in

Reactivity of oximes of 1-aryl(hetaryl)-2-(hydroxyamino)propan-1-ones with ethyl glyoxylate

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Alkyl(hetero)aromatic α-hydroxyamino oximes with the anti configuration of the oxime group reacted with ethyl glyoxylate to form 5-aryl(hetaryl)-1-hydroxy-1H-imidazole-2-carboxylic acid ethyl esters. In the case of 4-fluorophenyl-, 4-chlorophenyl-, and 4-methoxyphenyl-substituted α-hydroxyamino oximes, 3-aryl-5-hydroxy-5,6-dihydro-4H-1,2,5-oxadiazine-6-carboxylic acid ethyl esters were also formed. The positions of the substituents in the imidazole ring were established on the basis of a comparative analysis of the spectroscopic data of these products and the synthesized isomeric compound, 1-hydroxy-5-methyl-4-phenyl-1H-imidazole-2-carboxylic acid ethyl ester. 5-Aryl(hetaryl)-1H-imidazole-2-carboxylic acids were obtained in the reaction of 5-aryl(hetaryl)-1-hydroxy-1H-imidazole-2-carboxylic acids ethyl esters with chloroacetone.

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. Nikitina, P. A.; Perevalov, V. P. Chem. Heterocycl. Compd. 2017, 53, 123. [Khim. Geterotsikl. Soedin. 2017, 53, 123.]

  2. (а) Stensbøl, T. B.; Uhlmann, P.; Morel, S.; Eriksen, B. L.; Felding, J.; Kromann, H.; Hermit, M. B.; Greenwood, J. R.; Braüner-Osborne, H.; Madsen, U.; Junager, F.; Krogsgaard-Larsen, P.; Begtrup, M.; Vedsø, P. J. Med. Chem. 2002, 45, 19. (b) Eriksen, B. L.; Vedsø, P.; Morel, S.; Begtrup M. J. Org. Chem. 1998, 63, 12.

  3. Havez, S.; Begtrup, M.; Vedsø, P.; Andersen, K.; Ruhland, T. J. Org. Chem. 1998, 63, 7418.

    Article  CAS  PubMed  Google Scholar 

  4. (а) Amitina, S. A.; Tikhonov, A. Ya.; Grigor'ev, I. A.; Gatilov, Yu. V.; Selivanov, B. A. Chem. Heterocycl. Compd. 2009, 45, 691. [Khim. Geterotsikl. Soedin., 2009, 868.] (b) Nikolaenkova, E. B.; Tikhonov, A. Ya.; Amitina, S. A.; Gatilov, Yu. V. Chem. Heterocycl. Compd. 2014, 50, 699. [Khim. Geterotsikl. Soedin. 2014, 761.]

  5. (a) Wang, X.; Zhao, C.; Gao, L.; Zhou, Y.; Xu, L. J. Heterocycl. Chem. 2018, 55, 2619. (b) Song, Z.; DeMarco, A.; Zhao, M.; Corley, E. G.; Thompson, A. S.; McNamara, J.; Li, Y.; Rieger, D.; Sohar, P.; Mathre, D. J.; Tschaen, D. M.; Reamer, R. A.; Huntington, M. F.; Ho, G.-J.; Tsay, F.-R.; Emerson, K.; Shuman, R.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 1859. (c) Galeazzi, E.; Guzmán, A.; Nava, J. L.; Liu, Y.; Maddox, M. L.; Muchowski, J. M. J. Org. Chem. 1995, 60, 1090.

  6. Jarrad, A. M.; Debnath, A.; Miyamoto, Y.; Hansford, K. A.; Pelingon, R.; Butler, M. S.; Bains, T.; Karoli, T.; Blaskovich, M. A. T.; Eckmann, L.; Cooper, M. A. Eur. J. Med. Chem. 2016, 120, 353.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. (a) Shiga, N.; Takayanagi, S.; Muramoto, R.; Murakami, T.; Qin, R.; Suzuki, Y.; Shinohara, K.; Kaneda, A.; Nemoto, T. Bioorg. Med. Chem. Lett. 2017, 27, 2197. (b) Guo, C.; Kawamoto, Y.; Asamitsu, S.; Sawatani, Y.; Hashiya, K.; Bando, T.; Sugiyama, H. Bioorg. Med. Chem. 2015, 23, 855.

  8. Selivanov, B. A.; Tikhonov, A. Ya. Russ. Chem. Bull., Int. Ed. 2013, 62, 1232. [Izv. Akad. Nauk, Ser. Khim. 2013, 1232.]

  9. van Hirschheydt, T.; Voss, E. US Patent 20050085473; Chem. Abstr. 2005, 142, 411373.

  10. (a) Samsonov, V. A. Russ. J. Org. Chem. 2017, 53, 66. [Zh. Org. Khim. 2017, 53, 71.] (b) Nikolaenkova, E. B.; Os'kina, I. A.; Tikhonov, A. Ya. Russ. J. Org. Chem. 2017, 53, 1887. [Zh. Org. Khim. 2017, 53, 1851.]

  11. Amitina, S. A.; Grigor'ev, I. A.; Tikhonov, A. Ya. Russ. Chem. Bull., Int. Ed. 2006, 55, 1046. [Izv. Akad. Nauk, Ser. Khim. 2006, 1008.]

  12. Volodarskii, L. B.; Koptyug, V. A.; Lysak, А. N. Zh. Obshch. Khim. 1966, 2, 114; Chem. Abstr. 1966, 64, 75637.

Download references

The authors are grateful to the Chemical Service Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences for conducting spectral and analytical studies.

The authors are indebted to V. M. Mamatyuk (N. N. Vorozhtsov Institute of Organic Chemistry of the Siberian Branch of the Russian academy of Sciences) for his help in recording and discussing the 13C NMR spectra of imidazoles and Candidate of Chemical Sciences S. A. Amitina for participation in carrying out the synthetic experiments.

Author information

Authors and Affiliations

  1. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk, 630090, Russia

    Elena B. Nikolaenkova, Alexei Ya. Tikhonov & Stanislav Yu. Grishchenko

Authors
  1. Elena B. Nikolaenkova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alexei Ya. Tikhonov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Stanislav Yu. Grishchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alexei Ya. Tikhonov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(2), 142–146

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikolaenkova, E.B., Tikhonov, A.Y. & Grishchenko, S.Y. Reactivity of oximes of 1-aryl(hetaryl)-2-(hydroxyamino)propan-1-ones with ethyl glyoxylate. Chem Heterocycl Comp 55, 142–146 (2019). https://doi.org/10.1007/s10593-019-02430-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02430-8

Keywords

Search

Navigation