Skip to main content
SpringerLink
Log in

Synthesis of pyrido[2,3-a]phenazines by intramolecular cyclization of 7-arylamino-8-nitrosoquinolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Intramolecular heterocyclization reaction of 7-arylamino-8-nitrosoquinolines was used to obtain previously unknown pyrido[2,3-a]phenazine derivatives. The reaction was performed in refluxing acetic acid. The final products, including unsubstituted pyrido[2,3-a]phenazine, were obtained in good yields.

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.
Figure 2.

Similar content being viewed by others

References

  1. (a) Laursen, J. B.; Nielsen, J. Chem. Rev. 2004, 104, 1663. (b) Makgatho, M. E.; Anderson, R.; O'Sullivan, J. F.; Egan, T. J.; Freese, J. A.; Cornelius, N.; Van Rensburg, C. E. J. Drug Dev. Res. 2000, 50, 195. (c) Vicker, N.; Burgess, L.; Chuckowree, I. S.; Dodd, R.; Folkes, A.; Hardick, D. J.; Hancox, T. C.; Miller, W.; Milton, J.; Sohal, S.; Wang, S.; Wren, S. P.; Charlton, P.; Dangerfield, W.; Liddle, C.; Mistry, P.; Stewart, A.; Denny, W. A. J. Med. Chem. 2002, 45, 721. (d) Jobson, A. G.; Willmore, E.; Tilby, M. J.; Mistry, P.; Charlton, P.; Austin, C. A. Cancer Chemother. Pharmacol. 2009, 63, 889. (e) Cimmino, A.; Evidente, A.; Mathieu, V. ; Andolfi, A.; Lefranc, F.; Kornienko, A.; Kiss, R. Nat. Prod. Rep. 2012, 29, 487. (f) Gamage, S. A.; Spicer, J. A.; Rewcastle, G. W.; Milton, J.; Sohal, S.; Dangerfield, W.; Mistry, P.; Vicker, N.; Charlton, P. A.; Denny, W. A. J. Med. Chem. 2002, 45, 740. (g) Milton, J.; Vicker, N.; Denny, W. A.; Gamage, S. A.; Spicer, J. A. US Patent 2003, 6552021 B2.

  2. (a) Fischer, B. B.; Krieger-Liszkay, A.; Eggen, R. I. L. Environ. Sci. Technol. 2004, 38, 6307. (b) Larionov, S. V.; Kokina, T. E.; Plyusnin, V. F.; Glinskaya, L. A.; Tkachev, A. V.; Bryleva, Y. A.; Kuratieva, N. V.; Rakhmanova, M. I.; Vasilyev, E. S. Polyhedron 2014, 77, 75.

  3. Banerjee, S. ARKIVOC 2016, (i), 82.

  4. Gu, P.-Y.; Zhao, Y.; He, J.-H.; Zhang, J.; Wang, C.; Xu, Q.-F.; Lu, J.-M.; Sun, X. W.; Zhang, Q. J. Org. Chem. 2015, 80, 3030.

    Article  CAS  PubMed  Google Scholar 

  5. Wohl, A.; Aue, W. Chem. Ber. 1901, 34, 2442.

    Article  Google Scholar 

  6. (a) Chaudhary, A.; Khurana, J. M. Res. Chem. Intermed. 2018, 44, 1045. (b) Gulevskaya, A. V. Eur. J. Org. Chem. 2016, 24, 4207. (c) Kumar, K. S.; Bhaskar, B.; Ramulu, M. S.; Kumar, N. P.; Ashfaq, M. A.; Pal, M. Org. Biomol. Chem. 2017, 15, 82. (d). Aoki, Y.; O'Brien, H.; Kawasaki, H.; Takaya, H.; Nakamura, M. Org. Lett. 2019, 21, 461. (e) Nozawa-Kumada, K.; Abe, E.; Ito, S.; Shigeno, M.; Kondo, Y. Org. Biomol. Chem. 2018, 16, 3095.

  7. (a) Wrobel, Z; Kwast, A. Synlett 2007, 1525. (b) Wrobel, Z; Kwast, A. Synthesis 2010, 3865. (c) Kwast, A.; Stachowska, K.; Wróbel, Z.; Trawczyn'ski, A. Tetrahedron. Lett. 2011, 52, 6484. (d) Wróbel, Z.; Plichta, K; Kwast, A. Tetrahedron 2017, 73, 3147. (e) Wróbel, Z.; Więcław, M.; Bujok, R.; Wojciechowski, K. Monatsh. Chem. 2013, 144, 1847.

  8. Vasilyev, E. S.; Agafontsev, A. M.; Kolesnik, V. D.; Gatilov, Y. V.; Tkachev, A. V. Mendeleev Commun. 2011, 21, 253.

    Article  CAS  Google Scholar 

  9. Demidov, O. P.; Pobedinskaya, D. Yu.; Avakyan, E. K.; Amangasieva, G. A.; Borovlev, I. V. Chem. Heterocycl. Compd. 2018, 54, 875. [Khim. Geterotsikl. Soedin. 2018, 54, 875.]

  10. Gottlieb, H. E.; Kotlyar, V.; Nudelman, A. J. Org. Chem. 1997, 62, 7512.

    Article  CAS  PubMed  Google Scholar 

  11. CrysAlisPro, version 1.171.38.41; Rigaku Oxford Diffraction, 2015. https://www.rigaku.com/en/products/smc/crysalis.

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

    Article  CAS  Google Scholar 

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

    Google Scholar 

  14. 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 

Download references

This work received financial support from the Ministry of Education and Science of the Russian Federation within the framework of the State Assignment (project No. 4.6306.2017/8.9).

Author information

Authors and Affiliations

  1. North-Caucasus Federal University, 1a Pushkina St., Stavropol, 355009, Russia

    Diana Yu. Pobedinskaya, Oleg P. Demidov, Ivan V. Borovlev, Elena K. Avakyan & Gulminat A. Amangasieva

Authors
  1. Diana Yu. Pobedinskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Oleg P. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ivan V. Borovlev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Elena K. Avakyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Gulminat A. Amangasieva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Oleg P. Demidov.

Additional information

Supplementary information file containing 1Н and 13С NMR spectra for all synthesized compounds is available at the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 684–687

Electronic supplementary material

ESM 1

(PDF 1603 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pobedinskaya, D.Y., Demidov, O.P., Borovlev, I.V. et al. Synthesis of pyrido[2,3-a]phenazines by intramolecular cyclization of 7-arylamino-8-nitrosoquinolines. Chem Heterocycl Comp 55, 684–687 (2019). https://doi.org/10.1007/s10593-019-02518-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02518-1

Keywords

Search

Navigation