3-Azido-4,6-diarylthienopyridines obtained from the corresponding 3-amino derivatives are convenient precursors in the synthesis of the peri-annulated heterocyclic system, benzo(furo,thieno)[c]thieno[2,3,4-i,j]-2,7-naphthyridines. The spectral characteristics of the obtained compounds (IR, UV, NMR (1H, 13C, 1H–15N gHMBC) spectra, luminescence spectra, mass spectra) were studied. Computational prediction of potential biological action has been performed.
Similar content being viewed by others
References
Kaigorodova, E. A.; Vasilin, V. K.; Lipunov, М. М.; Zavodnik, V. E.; Krapivin, G. D. Chem. Heterocycl. Compd. 2004, 40, 1600. [Khim. Geterotsikl. Soedin. 2004, 1853.]
Vasilin, V. K.; Kaigorodova, E. A.; Firgang, S. I.; Krapivin, G. D. Chem. Heterocycl. Compd. 2004, 40, 377. [Khim. Geterotsikl. Soedin. 2004, 462.]
Kanishcheva, E. A.; Vasilin, V. K.; Kasimova, D. R.; Stroganova, T. A.; Krapivin, G. D. Chem. Heterocycl. Compd. 2013, 48, 1883. [Khim. Geterotsikl. Soedin. 2012, 2005.]
Kanishcheva, E. A.; Vasilin, V. K.; Stroganova, T. A.; Krapivin, G. D. Chem. Heterocycl. Compd. 2013, 49, 1387. [Khim. Geterotsikl. Soedin. 2013, 1488.]
Pokhodylo, N. T.; Matiychuk, V. S.; Obushak, N. D. Chem. Heterocycl. Compd. 2009, 45, 881. [Khim. Geterotsikl. Soedin. 2009, 1100.]
Vasilin, V. K.; Kanishcheva, E. A.; Stroganova, T. A.; Krapivin, G. D. Synlett 2015, 755.
Kanishcheva, E. A.; Bedareva, V. O.; Vasilin, V. K.; Stroganova, T. A.; Krapivin, G. D. Chem. Heterocycl. Compd. 2019, 55, 882. Khim. Geterotsikl. Soedin. 2019, 55, 882.]
Elgeneie, G. E.; Attia, A. M. E.; Fathy, N. M. J. Chem. Res., Synop. 1996, 112.
(a) Ershov, O. V.; Shishlikova, M. A.; Ievlev, M. Yu.; Belikov, M. Yu.; Maksimova, V. N. Tetrahedron 2019, 75, 130465. (b) Kalugin, V. E.; Shestopalov, A. M. Russ. Chem. Bull., Int. Ed. 2018, 67, 1492. [Izv. Akad. Nauk, Ser. Khim. 2018, 1492.] (c) Kalugin, V. E.; Shestopalov, A. M. Russ. Chem. Bull., Int. Ed. 2019, 68, 357. [Izv. Akad. Nauk, Ser. Khim. 2019, 357.]
Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
Brouwer, A. M. Pure Appl. Chem. 2011, 83, 2213.
Poroikov, V. V.; Filimonov, D. А.; Lagunin, А. А.; Gloriozova, T. А. in Sovremennye aspekty khimii geterotsiklov (Modern Aspects of Heterocycle Chemistry [in Russian]); Kartsev, V. G., Ed.; Moscow: ICSPF, 2010, p. 142.
(a) Vassiliev, P. M.; Spasov, A. A.; Kosolapov, V. A.; Kucheryavenko, A. F.; Gurova, N. A.; Anisimova, V. A. In Challenges and Advances in Computational Chemistry and Physics; Leszczynski, J., Ed.; Vol. 17. Application of Computational Techniques in Pharmacy and Medicine; Gorb, L., Kuz'min, V., Muratov, E., Eds.; Springer; Dordrecht, 2014, p. 369.
Certificate of State registration of a computer program No. 2011618547; IT Microcosm; Vassiliev, P. M., Kochetkov, А. N. (Russia). No. 201616643; appl. 02.09.2011; reg. 31.10.2011; publ. 20.03.2012; Bulletin of "“Computer Programs. Databases. Topographies of Integrated Circuits" 2012, 1(78), 209.
Vandael, D.; Gounko, N. V. Transl. Psychiatry 2019, 9, 272.
Acknowledgement
This work was supported by the Ministry of Science and Higher Education of the Russian Federation (agreement FZEZ-2020-0004) and the Russian Foundation for Basic Research (grant 18-33-00184/18).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(8), 1078–1091
Electronic supplementary material
ESM 1
(PDF 424 kb)
Rights and permissions
About this article
Cite this article
Vasilin, V.K., Kanishcheva, E.A., Stroganova, T.А. et al. 3-Amino(azido)-4,6-aryl(hetaryl)thieno[2,3-b]pyridines and benzo(furo,thieno)[c]thieno[2,3,4-i,j]-2,7-naphthyridines on their basis: synthesis, spectral properties, and prediction of biological activity. Chem Heterocycl Comp 56, 1078–1091 (2020). https://doi.org/10.1007/s10593-020-02777-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-020-02777-3