Skip to main content
SpringerLink
Log in

2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides 7*. Synthesis of 4-amino-1-aryl-6-halo-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-с]pyridine-7-carbonitriles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2-acyl(aroyl)-1,1,3,3-tetracyanopropenides with gaseous hydrogen halides was used to obtain 2-amino-3-aroyl(acyl)-6-halopyridine-3,5-dicarbonitriles, which were subsequently converted to the respective 4-amino-1-aryl-6-halo-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles by treatment with concentrated sulfuric acid, followed by aqueous workup.

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.
Figure 3.

Similar content being viewed by others

References

  1. Kayukov, Ya. S.; Karpov, S. V.; Bardasov, I. N.; Kayukova, O. V.; Ershov, O. V.; Nasakin, O. E. Russ. J. Org. Chem. 2012, 48, 1107. [Zh. Org. Khim. 2012, 48, 1109.]

  2. Karpov, S. V.; Grigor'ev, A. A.; Kayukov, Ya. S.; Karpova, I. V.; Nasakin, O. E.; Tafeenko, V. A. J. Org. Chem. 2016, 81, 6402.

    Article  CAS  Google Scholar 

  3. Grigor'ev, A. A.; Karpov, S. V.; Kayukov, Ya. S.; Nasakin, O. E.; Tafeenko, V. A. Synlett 2015, 2313.

  4. Karpov, S. V.; Kayukov, Ya. S.; Bardasov, I. N.; Kayukova, O. V.; Ershov, O. V.; Nasakin, O. E. Russ. J. Org. Chem. 2011, 47, 405. [Zh. Org. Khim. 2011, 47, 412.]

  5. Karpov, S. V.; Kayukov, Ya. S.; Bardasov, I. N.; Ershov, O. V.; Nasakin, O. E.; Kayukova, O. V. Russ. J. Org. Chem. 2011, 47, 1161. [Zh. Org. Khim. 2011, 47, 1144.]

  6. Karpov, S. V.; Kayukov, Ya. S.; Bardasov, I. N.; Kayukova, O. V.; Lipin, K. V.; Nasakin, O. E. Russ. J. Org. Chem. 2011, 47, 1492. [Zh. Org. Khim. 2011, 47, 1467.]

  7. Kayukov, Ya. S.; Karpov, S. V.; Kayukova, O. V.; Ershov, O. V.; Nasakin, O. E. Russ. J. Org. Chem. 2014, 50, 1097. [Zh. Org. Khim. 2014, 50, 1116.]

  8. Grigor'ev, A. А.; Karpov, S. V.; Kayukov, Ya. S.; Belikov, M. Yu.; Nasakin, O. E. Tetrahedron Lett. 2015, 56, 6279.

    Article  Google Scholar 

  9. Kayukov, Ya. S.; Karpov, S. V.; Rizatdinov, M. M.; Bardasov, I. N.; Ershov, O. V.; Nasakin, O. E.; Tafeenko, V. A. Russ. J. Org. Chem. 2013, 49, 707. [Zh. Org. Khim. 2013, 49, 724.]

  10. Grigor'ev, A. A.; Karpov, S. V.; Kayukov, Y. S.; Nasakin, O. E.; Gracheva, I. A.; Tafeenko, V. A. Chem. Heterocycl. Compd. 2017, 53, 230. [Khim. Geterotsikl. Soedin. 2017, 53, 230.]

  11. Cappelli, A.; Anzini, M.; Vomero, S.; Mennuni, L.; Makovec, F.; Doucet, E.; Hamon, M.; Menziani, M. C.; De Benedetti, P. G.; Giorgi, G.; Ghelardini, C.; Collina, S. Bioorg. Med. Chem. 2002, 10, 779.

    Article  CAS  Google Scholar 

  12. Kravchenko, D. V.; Kuzovkova, Y. A.; Kysil, V. M.; Tkachenko, S. E.; Maliarchouk, S.; Okun, I. M.; Balakin, K. V.; Ivachtchenko, A. V. J. Med. Chem. 2005, 48, 3680.

    Article  CAS  Google Scholar 

  13. Kosulina, T. P.; Kaigorodova, E. A.; Kul'nevich, V. G.; Sapunov, A. Ya.; Govorova, S. A. Pharm. Chem. J. 1997, 31, 191. [Khim.-Farm. Zh. 1997, 31(4), 30.]

  14. Delaine, T.; Bernardes-Génisson, V.; Meunier, B.; Bernadou, J. J. Org. Chem. 2007, 72, 675.

    Article  CAS  Google Scholar 

  15. Delaine, T.; Bernardes-Génisson, V.; Stigliani, J.-L.; Gornitzka, H.; Meunier, B.; Bernadou, J. Eur. J. Org. Chem. 2007, 1624.

  16. Delaine, T.; Bernardes-Génisson, V.; Quémard, A.; Constant, P.; Meunier, B.; Bernadou, J. Eur. J. Med. Chem. 2010, 45, 4554.

    Article  CAS  Google Scholar 

  17. Broussy, S.; Bernardes-Génisson, V.; Quémard, A.; Meunier, B.; Bernadou, J. J. Org. Chem. 2005, 70, 10502.

    Article  CAS  Google Scholar 

  18. Broussy, S.; Bernardes-Génisson, V.; Coppel, Y.; Quémard, A.; Bernadou, J.; Meunier, B. Org. Biomol. Chem. 2005, 3, 670.

    Article  CAS  Google Scholar 

  19. Kayukov, Ya. S.; Bardasov, I. N.; Karpov, S. V.; Ershov, O. V.; Nasakin, O. E.; Kayukova, O. V.; Tafeenko, V. A. Russ. J. Org. Chem. 2012, 48, 1447. [Zh. Org. Khim. 2012, 48, 1463.]

  20. https://www.stoe.com/product/software-x-area/

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

    Article  Google Scholar 

  22. Brandenburg, K. DIAMOND, Release 2.1d; Crystal Impact GbR: Bonn, 2000.

    Google Scholar 

Download references

Acknowledgements

This work was performed with support from the Scholarship of the President of the Russian Federation for young scientists and doctoral students SP-3725.2015.4.

X-ray structural analysis was performed with support from the program for development of the M. V. Lomonosov Moscow State University.

Author information

Authors and Affiliations

  1. Chuvash State University named after I. N. Ulyanov, 15 Moskovsky Ave., Cheboksary, 428015, Russia

    Yakov S. Kayukov, Sergey V. Karpov, Arthur A. Grigor’ev, Anastasiya L. Nikiforova & Oleg E. Nasakin

  2. N. I. Lobachevsky State University of Nizhny Novgorod, 23 Gagarina Ave., Nizhny Novgorod, 603950, Russia

    Ekaterina S. Shchegravina

  3. Chuvash State Agricultural Academy, 29 Karla Marksa St., Cheboksary, 428032, Russia

    Olga V. Kayukova

  4. M. V. Lomonosov Moscow State University, 1 Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Victor A. Tafeenko

Authors
  1. Yakov S. Kayukov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sergey V. Karpov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Arthur A. Grigor’ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Anastasiya L. Nikiforova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Oleg E. Nasakin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ekaterina S. Shchegravina
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Olga V. Kayukova
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Victor A. Tafeenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sergey V. Karpov.

Additional information

* For Communication 6, see 1.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(5), 568–574

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kayukov, Y.S., Karpov, S.V., Grigor’ev, A.A. et al. 2-Acyl(aroyl)-1,1,3,3-tetracyanopropenides 7*. Synthesis of 4-amino-1-aryl-6-halo-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-с]pyridine-7-carbonitriles. Chem Heterocycl Comp 53, 568–574 (2017). https://doi.org/10.1007/s10593-017-2093-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2093-x

Keywords

Search

Navigation