Skip to main content
SpringerLink
Log in

Imidazol-5-one-based donor–acceptor cyclopropanes in reaction with C=S dipolarophiles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Interaction of imidazol-5-one-based donor–acceptor cyclopropanes with thiourea and thioacetamide was studied. Previously undescribed spirocyclic 2-amino- and 2-iminotetrahydrothiophenes are formed in the reaction.

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

Figure 1.

Similar content being viewed by others

References

  1. (a) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151. (b) Schneider, T. F.; Kaschel, J.; Werz, D. B. Angew. Chem., Int. Ed. 2014, 53, 5504.

  2. (a) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704. (b) de Nanteuil, F.; Waser, J. Angew. Chem., Int. Ed. 2011, 50, 12075. (c) Trost, B. M.; Morris, P. J. Angew. Chem., Int. Ed. 2011, 50, 6167. (d) Racine, S.; de Nanteuil, F.; Serrano, E.; Waser, J. Angew. Chem., Int. Ed. 2014, 53, 8484.

  3. (a) Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014. (b) Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642. (c) Parsons, A. T.; Johnson, J. S. J. Am. Chem. Soc. 2009, 131, 3122.

  4. (a) Carson, C. A.; Kerr, M. A. J. Org. Chem. 2005, 70, 8242. (b) Jackson, S. K.; Karadeolian, A.; Driega, A. B.; Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196. (c) Parsons, A. T.; Smith, A. G.; Neel, A. J.; Johnson, J. S. J. Am. Chem. Soc. 2010, 132, 9688. (d) Preindl, J.; Chakrabarty, S.; Waser, J. Chem. Sci. 2017, 8, 7112. (e) Zhang, M.-C.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M.; You, S.-L. Chem 2019, 5, 156.

  5. Chakrabarty, S.; Chatterjee, I.; Wibbeling, B.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2014, 53, 5964.

  6. (a) Korotkov, V. S.; Larionov, O. V.; Hofmeister, A.; Magull, J.; de Meijere, A. J. Org. Chem. 2007, 72, 7504. (b) Tomilov, Y. V.; Novikov, R. A.; Nefedov, O. M. Tetrahedron 2010, 66, 9151.

  7. (a) Yadav, V. K.; Sriramurthy, V. Angew. Chem., Int. Ed. 2004, 43, 2669. (b) Racine, S.; Hegedüs, B.; Scopelliti, R.; Waser, J. Chem.–Eur. J. 2016, 22, 11997. (c) Pagenkopf, B. L.; Yu, M. Org. Lett. 2003, 5, 5099. (d) Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122. (e) Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023. (f) Sibi, M. P.; Ma, Z.; Jasperse, C. P. J. Am. Chem. Soc. 2005, 127, 5764. (g) Kang, Y.-B.; Sun, X.-L.; Tang, Y. Angew. Chem., Int. Ed. 2007, 46, 3918. (h) Xu, P.-W.; Liu, J.-K.; Shen, L.; Cao, Z.-Y.; Zhao, X.-L.; Yan, J.; Zhou, J. Nat. Commun. 2017, 8, 1619.

  8. (a) Augustin, A. U.; Sensse, M.; Jones, P. G.; Werz, D. B. Angew. Chem., Int. Ed. 2017, 56, 14293. (b) Augustin, A. U.; Busse, M.; Jones, P. G.; Werz, D. B. Org. Lett. 2018, 20, 820. (c) Kreft, A.; Jones, P. G.; Werz, D. B. Org. Lett. 2018, 20, 2059.

  9. Matsumoto, Y.; Nakatake, D.; Yazaki, R.; Ohshima, T. Chem.–Eur. J. 2018, 24, 6062.

  10. Xie, M.-S.; Zhao, G.-F.; Qin, T.; Suo, Y.-B.; Qua, G.-R.; Guo, H.-M. Chem. Commun. 2019, 55, 1580.

  11. (a) Mikhaylov, A. A.; Kuleshov, A. V.; Solyev, P. N.; Korlyukov, A. A.; Dorovatovskii, P. V.; Mineev, K. S.; Baranov, M. S. Org. Lett. 2020, 22, 2740. (b) Mikhaylov, A. A.; Solyev, P. N.; Kuleshov, A. V.; Kublitskii, V. S.; Korlyukov, A. A.; Lushpa, V. A.; Baranov, M. S. Chem. Heterocycl. Compd. 2020, 56, 1092.

  12. Huang, Y.; Dömling, A. Mol. Diversity 2011, 15, 3.

  13. (a) Gewald, K.; Schinke, E.; Böttcher, H. Chem. Ber. 1966, 99, 94. (b) Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 333. (c) Özbek, H.; Veljkovic, I. S.; Reissig, H.-U. Synlett 2008, 3145.

  14. Ikonnikova, V. A.; Zhigileva, E. A.; Kuleshov, A. V.; Shirokova, V. V.; Baranov, M. S.; Mikhaylov A. A. Mendeleev Commun. 2021, 31, 657.

  15. Baldridge, A.; Kowalik, J.; Tolbert, L. M. Synthesis 2010, 2424.

  16. Chen, K.-Y.; Cheng, Y.-M.; Lai, C.-H.; Hsu, C.-C.; Ho, M.-L.; Lee, G.-H.; Chou, P.-T. J. Am. Chem. Soc. 2007, 129, 4534.

  17. Zaitseva, S. O.; Golodukhina, S. V.; Baleeva, N. S.; Levina, E. A.; Smirnov, A. Yu.; Zagudaylova, M. B.; Baranov, M. S. ChemistrySelect 2018, 3, 8593.

  18. Chen, Y.-H.; Lo, W.-J.; Sung, K. J. Org. Chem. 2013, 78, 301.

  19. APEX3, RLATT, CELL_NOW, TWINABS, SAINT-Plus, SADABS; Bruker AXS Inc.: Madison, 2016.

  20. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2015, A71, 3.

  21. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

  22. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J, Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

Download references

The authors gratefully acknowledge support from the Russian Science Foundation, grant No. 20-73-10195.

A. A. Korlyukov acknowledges the Ministry of Science and Higher Education of the Russian Federation (Contract/agreement No. 075-00697-22-00) for support of employment of the equipment of Center for Molecular Composition Studies of A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russia

    Semen E. Nikolaev, Anatolii I. Sokolov, Andrey A. Mikhaylov, Nadezhda S. Baleeva, Mikhail S. Baranov & Ivan N. Myasnyanko

  2. Pirogov Russian National Research Medical University, 1 Ostrovitianov St., Moscow, 117997, Russia

    Anatolii I. Sokolov, Alexander A. Korlyukov, Nadezhda S. Baleeva, Mikhail S. Baranov & Ivan N. Myasnyanko

  3. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28/1 Vavilova St., Moscow, 119334, Russia

    Alexander A. Korlyukov

Authors
  1. Semen E. Nikolaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anatolii I. Sokolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Andrey A. Mikhaylov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alexander A. Korlyukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Nadezhda S. Baleeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Mikhail S. Baranov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ivan N. Myasnyanko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ivan N. Myasnyanko.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2022, 58(12), 756–763

Supplementary Information

ESM 1

(PDF 5318 kb)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikolaev, S.E., Sokolov, A.I., Mikhaylov, A.A. et al. Imidazol-5-one-based donor–acceptor cyclopropanes in reaction with C=S dipolarophiles. Chem Heterocycl Comp 58, 756–763 (2022). https://doi.org/10.1007/s10593-023-03153-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03153-7

Keywords

Search

Navigation