Skip to main content
SpringerLink
Log in

Reversible condensation of 4-arylidene-1,2-dimethyl-1H-imidazol-5(4H)-ones with aromatic acyl chlorides

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

(Z)-1,2-Dimethyl-4-(4-methoxybenzylidene)-1H-imidazol-5(4H)-one underwent a condensation reaction with aromatic acyl chlorides, forming keto derivatives that were structurally similar to chromophores of red fluorescent proteins, as well as to the products of their maturation and/or degradation. The reverse reaction of the obtained products was observed upon treatment with aqueous alkali.

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

Notes

  1. Here and further for compounds 4a-e the total yield of two steps based on the starting imidazolone 1 is shown.

References

  1. Ivashkin, P. E.; Yampolsky, I. V.; Lukyanov, K. A. Bioorg. Khim. 2009, 35, 726.

    CAS  Google Scholar 

  2. Song, W.; Strack, R. L.; Jaffrey, S. R. Nat. Methods 2013, 10, 873.

    Article  CAS  Google Scholar 

  3. Yuan, L.; Lin, W.; Chen, H.; Zhu, S.; He, L. Angew. Chem. 2013, 125, 10202.

    Article  Google Scholar 

  4. Fery-Forgues, S.; Veesler, S.; Brett Fellows, W.; Tolbert, L. M.; Solntsev, K. M. Langmuir 2013, 29, 14718.

    Article  CAS  Google Scholar 

  5. Deng, H.; Zhu, Q.; Wang, D.; Tu, C.; Zhu, B.; Zhu, X. Polym. Chem. 2012, 3, 1975.

    Article  CAS  Google Scholar 

  6. Baranov, M. S.; Lukyanov, K. A.; Borissova, A. O.; Shamir, J.; Kosenkov, D.; Slipchenko, L. V.; Tolbert, L. M.; Yampolsky, I. V.; Solntsev, K. M. J. Am. Chem. Soc. 2012, 134, 6025.

    Article  CAS  Google Scholar 

  7. Da Silva, R. B.; Loback, V. B.; Salomão, K.; de Castro, S. L.; Wardell, J. L.; Wardell, S. M. S. V.; Costa, T. E. M. M.; Penido, C.; de Henriques, M. G. M. O.; Carvalho, S. A.; da Silva, E. F.; Fraga, C. A. M. Molecules 2013, 18, 3445.

    Article  Google Scholar 

  8. Dzvinchuk, I. B.; Gutov, O. V.; Chernega, A. N.; Lozinskii, M. O. Chem. Heterocycl. Compd. 2010, 46, 684. [Khim. Geterotsikl. Soedin. 2010, 852.]

  9. (a) Cozzi, P.; Pillan, A. J. Heterocycl. Chem. 1986, 23, 1693. (b) Macco, A. A.; Godefroi, E. F.; Drouen, J. J. M. J. Org. Chem. 1975, 40, 252.

  10. Chuang, W.-T.; Chen, B.-S.; Chen, K.-Y.; Hsieh, C.-C.; Chou, P.-T. Chem. Comm. 2009, 6982.

  11. Baleeva, N. S.; Myannik, K. A.; Yampolsky, I. V.; Baranov, M. S. Eur. J. Org. Chem. 2015, 26, 5716.

    Article  Google Scholar 

  12. Dong, J.; Solntsev, K. M.; Tolbert, L. M. J. Am. Chem. Soc. 2006, 128, 12038.

    Article  CAS  Google Scholar 

Download references

The study was performed with financial support from the Russian Foundation for Basic Research in the framework of the project No. 14-50-00131. The equipment of Collective Use Center of the Institute of Bioorganic Chemistry was used for part of this research.

Author information

Authors and Affiliations

  1. Institute of Bioorganic Chemistry named after Academicians M. M. Shemyakin and Yu. A. Ovchinnikov, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow, 117997, Russia

    Svetlana V. Golodukhina, Nadezhda S. Baleeva, Konstantin S. Mineyev & Mikhail S. Baranov

  2. Russian National Research Medical University named after N. I. Pirogov, 1 Ostrovityanova St., Moscow, 117997, Russia

    Nadezhda S. Baleeva & Mikhail S. Baranov

Authors
  1. Svetlana V. Golodukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nadezhda S. Baleeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Konstantin S. Mineyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mikhail S. Baranov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mikhail S. Baranov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(10), 944–947

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Golodukhina, S.V., Baleeva, N.S., Mineyev, K.S. et al. Reversible condensation of 4-arylidene-1,2-dimethyl-1H-imidazol-5(4H)-ones with aromatic acyl chlorides. Chem Heterocycl Comp 51, 944–947 (2015). https://doi.org/10.1007/s10593-015-1802-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1802-6

Keywords

Search

Navigation