Skip to main content
SpringerLink
Log in

The reaction of 4-aminocoumarin with β-carbonyl-substituted 4Н-chromenes: synthesis of 5H-chromeno[4,3-b]pyridin-5-one derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Reactions of 4Н-chromene-3-carbaldehydes and 1Н-benzo[f]chromene-3-carbaldehydes with 4-aminocoumarin were used to obtain a series of pyridocoumarin derivatives containing a 2-hydroxybenzyl or 2-hydroxy-1-naphthyl substituent at the β-position relative to the nitrogen atom. The reaction mechanism includes a Michael reaction, chromane ring opening, and cyclodehydration.

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.

Similar content being viewed by others

References

  1. (a) Mandal, T. K.; Kuznetsov, V. V.; Soldatenkov, A. T. Chem. Heterocycl. Compd. 1994, 30, 867. [Khim. Geterotsikl. Soedin. 1994, 1011.] (b) Núñez-Vergara, L. J.; Squella, J. A.; Navarrete-Encina, P. A.; Vicente-García, E.; Preciado, S.; Lavilla, R. Curr. Med. Chem. 2011, 18, 4761.

  2. (a) Thapa, P.; Jun, K.-Y.; Kadayat, T. M.; Park, C.; Zheng, Z.; Magar, T. B. T.; Bist, G.; Shrestha, A.; Na, Y.; Kwon, Y.; Lee, E.-S. Bioorg. Med. Chem. 2015, 23, 6454. (b) Thapa, U.; Thapa, P.; Karki, R.; Yun, M.; Choi, J. H.; Jahng, Y.; Lee, E.; Jeon, K.-H.; Na, Y.; Ha, E.-M.; Cho, W.-J.; Kwon, Y.; Lee, E.-S. Eur. J. Med. Chem. 2011, 46, 3201. (c) Neves, M. A. C.; Dinis, T. C. P.; Colombo, G.; Sá e Melo, M. L. Eur. J. Med. Chem. 2009, 44, 4121. (d) Mulakayala, N.; Rambabu, D.; Raja, M. R.; Chaitanya, M.; Kumar, C. S.; Kalle, A. M.; Krishna, G. R.; Reddy, C. M.; Rao, M. V. B.; Pal, M. Bioorg. Med. Chem. 2012, 20, 759. (e) Thapa, P.; Lee, E.-S. Bull. Korean Chem. Soc. 2012, 33, 3103.

  3. Hegab, M. I.; Abdel-Fattah, A.-S. M.; Yousef, N. M.; Nour, H. F.; Mostafa, A. M.; Ellithey, M. Arch. Pharm. Chem. Life Sci. 2007, 340, 396.

    Article  CAS  Google Scholar 

  4. Dawane, B. S.; Konda, S. G.; Bodade, R. G.; Bhosale, R. B. J. Heterocycl. Chem. 2010, 47, 237.

    Article  CAS  Google Scholar 

  5. (a) Chen, H.; Huang, M.; Li, X.; Liu, L.; Chen, B.; Wang, J.; Lin, Y. Fitoterapia 2018, 124, 103. (b) Huang, S. Z.; Cheng, B. H.; Ma, Q. Y.; Wang, Q.; Kong, F. D.; Dai, H. F.; Qiu, S. Q.; Zheng, P. Y.; Liu, Z. Q.; Zhao, Y.-X. RSC Adv. 2016, 6, 21139. (c) Zhou, F.-J.; Nian, Y.; Yan, Y.; Gong, Y.; Luo, Q.; Zhang, Y.; Hou, B.; Zuo, Z.-L.; Wang, S.-M.; Jiang, H.-H.; Yang, J.; Cheng, Y.-X. Org. Lett. 2015, 17, 3082. (d) Luo, Q.; Yang, X.-H.; Yang, Z.-L.; Tu, Z.-C.; Cheng, Y.-X. Tetrahedron 2016, 72, 4564. (e) Wang, X.-L.; Dou, M.; Luo, Q.; Cheng, L.-Z.; Yan, Y.-M.; Li, R.-T.; Cheng, Y.-X. Fitoterapia 2017, 116, 93. (f) Zhao, Z.-Z.; Chen, H.-P.; Feng, T.; Li, Z.-H.; Dong, Z.-J.; Liu, J.-K. J. Asian Nat. Prod. Res. 2015, 17, 1160.

  6. Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Targets Heterocycl. Syst. 2018, 22, 436.

    Google Scholar 

  7. Ivanov, I. C.; Karagiosov, S. K.; Simeonov, M. F. Arch. Pharm. (Weinheim) 1991, 324, 61.

    Article  CAS  Google Scholar 

  8. Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2018, 54, 1121. [Khim. Geterotsikl. Soedin. 2018, 54, 1121.]

    Article  CAS  Google Scholar 

  9. (a) Ling, F.; Xiao, L.; Fang, L.; Lv, Y.; Zhong, W. Adv. Synth. Catal. 2018, 360, 444. (b) Yadav, A.; Biswas, S.; Mobin, S. N.; Samanta, S. Tetrahedron Lett. 2017, 58, 3634. (c) Adib, M.; Peytam, F.; Rahmanian-Jazi, M.; Mohammadi-Khanaposhtani, M.; Mahernia, S.; Bijanzadeh, H. R.; Jahani, M.; Imanparast, S.; Faramarzi, M. A.; Mahdavi, M.; Larijani, B. New J. Chem. 2018, 42, 17268. (d) Weng, Y.; Zhou, H.; Sun, C.; Xie, Y.; Su, W. J. Org. Chem. 2017, 82, 9047. (e) Lee, Y. R. KR Patent 20180003668A.

  10. (a) Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Russ. Chem. Rev. 2017, 86, 625. [Usp. Khim. 2017, 86, 625.] (b) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. J. Org. Chem. 2017, 82, 1517. a Lukashenko, A. V.; Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Russ. J. Org. Chem. 2016, 52, 1817. [Zh. Org. Khim. 2016, 52, 1824.] (d) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2016, 52, 711. [Khim. Geterotsikl. Soedin. 2016, 52, 711.]

Download references

The reported study was funded by the Russian Foundation for Basic Research and the Samara Oblast according to the research project 17-43-630838 and was also supported by the Ministry of Education and Science of the Russian Federation within the framework of State Assignment (project 4.5628.2017/6.7).

Author information

Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeiskaya St., Samara, 443100, Russia

    Dmitriy V. Osipov, Alina A. Artyomenko, Vitaly A. Osyanin & Yuri N. Klimochkin

Authors
  1. Dmitriy V. Osipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alina A. Artyomenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vitaly A. Osyanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yuri N. Klimochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vitaly A. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 261–265

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Osipov, D.V., Artyomenko, A.A., Osyanin, V.A. et al. The reaction of 4-aminocoumarin with β-carbonyl-substituted 4Н-chromenes: synthesis of 5H-chromeno[4,3-b]pyridin-5-one derivatives. Chem Heterocycl Comp 55, 261–265 (2019). https://doi.org/10.1007/s10593-019-02451-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02451-3

Keywords

Search

Navigation