Skip to main content
Log in

The synthesis of novel heterocyclic 3-acetamide derivatives of benzanthrone

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Novel luminescent derivatives of benzanthrone were obtained in nucleophilic substitution reactions of 3-(2-chloroacetamido)-benzanthrone with a number of heterocyclic amines. The structures of the obtained compounds were confirmed by spectral data. Target products, due to pronounced luminescent properties, can be used to visualize biological objects.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5

Similar content being viewed by others

References

  1. (a) Bugaenko, D. I.; Karchava, A. V.; Yunusova, Z. A.; Yurovskaya, M. A. Chem. Heterocycl. Compd. 2019, 55, 483. [Khim. Geterotsikl. Soedin.2019, 55, 483.] (b) Gao, H.; Wu, X. Chem. Heterocycl. Compd.2018, 54, 125. [Khim. Geterotsikl. Soedin.2018, 54, 125.] (c) Pugachov, D. E.; Kostryukova, T. S.; Zatonsky, G. V.; Vatsadze, S. Z.; Vasil’ev, N. V. Chem. Heterocycl. Compd. 2018, 54, 528. [Khim. Geterotsikl. Soedin.2018, 54, 528.]

  2. (a) Kirilova, E. M; Meirovics, I. A; Belyakov, S. V. Chem. Heterocycl. Compd. 2002, 38, 789. [Khim. Geterotsikl. Soedin.2002, 896.] (b) Kirilova, E. M.; Kalnina, I.; Kirilov, G. K.; Meirovics, I. J. Fluoresc.2008, 18, 645. (c) Gonta, S.; Utinans, M.; Kirilov, G.; Belyakov, S.; Ivanova, I.; Fleisher, M.; Savenkov, V.; Kirilova, E. Spectrochim. Acta, Part A2013, 101, 325. (d) Kirilova, E. M.; Puckins, A. I.; Romanovska, E.; Fleisher, M.; Belyakov, S. V. Spectrochim. Acta, Part A2018, 202, 41.

  3. (a) Trusova, V. M.; Kirilova, E.; Kalnina, I.; Kirilov, G.; Zhytniakivska, O. A.; Fedorov, P. V.; Gorbenko, G. P. J. Fluoresc.2012, 22, 953. (b) Vus, K.; Trusova, V.; Gorbenko, G.; Kirilova, E.; Kirilov, G.; Kalnina, I.; Kinnunen, P. Chem. Phys. Lett. 2012, 532, 110. (c) Ryzhova, O.; Vus, K.; Trusova, V.; Kirilova, E.; Kirilov, G.; Gorbenko, G.; Kinnunen, P. Methods Appl. Fluoresc.2016, 4(3), 034007.

  4. Staneva, D.; Betcheva, R. Dyes Pigm.2007, 74, 148.

    Article  CAS  Google Scholar 

  5. Luttringhaus, A.; Neresheimer, H. Justus Liebigs Ann. Chem.1929, 473, 259.

    Article  Google Scholar 

  6. (a) Rama Rao, A. V.; Vaidyanathan, A. Spectrochim. Acta, Part A1981, 37, 145. (b) Ueda, T.; Abliz, Z.; Sato, M.; Nishimura, M.; Iwashima, S.; Aoki, J.; Kan, T.; Matsunaga, S.; Tanaka, R. J. Mol. Struct.1990, 224, 313. (c) Takekawa, M.; Aoki, J.; Iwashima, S.; Ueda, T. Magn. Reson. Chem. 1994, 32, 87.

  7. (a) Abliz, Z.; Ueda, T.; Kubogata, K.; Iwashima, S.; Takekawa, M.; Aoki, J.; Kan, T. Org. Mass Spectrom. 1990, 25, 345. (b) Holčapek, M.; Volná, K.; Vaněrková, D. Dyes Pigm. 2007, 75, 156.

  8. Lukevics, E.; Ignatovich, L.; Belyakov, S. V. Chem. Heterocycl. Compd. 2007, 43, 243. [Khim. Geterotsikl. Soedin.2007, 299.]

  9. Kapusta, P.; Machalický, O.; Hrdina, R.; Nepraš, M.; Zimmt, M. B.; Fidler, V. J. Phys. Chem. А2003, 107, 9740.

    Article  CAS  Google Scholar 

  10. (a) Grabowski, Z. R.; Rotkiewicz, K.; Rubaszewska, W.; Kirkor-Kaminsk, E. Acta Phys. Pol., A1978, 54, 767. (b) Grabowski, Z. R.; Rotkiewicz, K.; Rettig, W. Chem. Rev.2003, 103, 3899.

  11. Shivraj; Siddlingeshwar, B.; Kirilova, E. M.; Belyakov, S. V.; Divakar, D. D.; Alkheraif, A. A. Photochem. Photobiol. Sci.2018, 17, 453.

  12. Kirilova, E.; Mickevica, I.; Mežaraupe, L.; Puckins, A.; Rubenina, I.; Osipovs, S.; Kokina, I.; Bulanovs, A.; Kirjusina, M.; Gavarane, I. Luminescence2019, 34, 353.

    Article  CAS  Google Scholar 

  13. Gavarane, I.; Kirilova, E.; Rubeniņa, I.; Mežaraupe, L.; Osipovs, S.; Deksne, G.; Pučkins, A.; Kokina, I.; Bulanovs, A.; Kirjušina, M. Microsc. Microanal.2019, 25, 1491.

    Article  CAS  Google Scholar 

  14. Staneva, D.; Vasileva-Tonkova, E.; Kukeva, R.; Stoyanova, R.; Grabchev, I. J. Mol. Struct.2019, 1197, 576.

    Article  CAS  Google Scholar 

  15. Altomare, A.; Burla, M. С.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr.1999, 32, 115.

    Article  CAS  Google Scholar 

  16. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr.2008, A64, 112.

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

    Article  CAS  Google Scholar 

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

  19. Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. Acta Crystallogr., Sect. A: Found. Adv.2015, A71, 59.

Download references

This work was financially supported by the European Regional Development Fund (project No. 1.1.1.1/16/A/211).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Elena M. Kirilova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(2), 192–198

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kirilova, E.M., Nikolaeva, I.D., Romanovska, E. et al. The synthesis of novel heterocyclic 3-acetamide derivatives of benzanthrone. Chem Heterocycl Comp 56, 192–198 (2020). https://doi.org/10.1007/s10593-020-02644-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02644-1

Keywords

Navigation