Skip to main content
Log in

The synthesis of 3-nitro-4H-benzo[h]chromenes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of 3-nitro-4H-benzo[h]chromenes was developed based on the reaction of 1-naphthoquinone 2-methides generated in situ from Mannich bases with 4-(2-nitrovinyl)morpholine. It was shown that such nucleophiles as morpholine and 4-bromoaniline add to the double bond of the pyran ring.

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.

Similar content being viewed by others

References

  1. (a) Osyanin, V. A.; Lukashenko, A. V.; Osipov, D. V. Russ. Chem. Rev. 2021, 90, 324. (b) Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Russ. Chem. Rev. 2017, 86, 625.

  2. (a) Hegedűs, D.; Szemerédi, N.; Spengler, G.; Szatmári, I. Eur. J. Med. Chem. 2022, 237, 114391. (b) Büyükkidan, B.; Ceylan, M. J. Chem. Res., Synop. 2003, 749. (c) Fujiwara, M.; Sakamoto, M.; Komeyama, K.; Yoshida, H. Takaki, K. J. Heterocycl. Chem. 2015, 52, 59. (d) Bladé-Font, A.; de Mas Rocabayera, T. J. Chem. Soc., Perkin Trans. 1 1982, 841.

  3. (a) Semenova, I. A.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2022, 58, 656. (b) Chen, P.; Wang, K.; Guo, W.; Liu, X.; Liu, Y.; Li, C. Angew. Chem., Int. Ed. 2017, 56, 3689.

  4. (a) Osyanin, V. A.; Lukashenko, A. V.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2015, 50, 1528. (b) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2016, 52, 711. (c) Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. J. Org. Chem. 2017, 82, 1517.

  5. (a) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Barkov, A. Yu. Russ. Chem. Rev. 2013, 82, 1081. (b) Korotaev, V. Yu.; Kutyashev, I. B.; Barkov, A. Yu.; Sosnovskikh, V. Ya. Russ. Chem. Rev. 2019, 88, 27. (c) Vroemans, R.; Dehaen, W. Targets Heterocycl. Syst. 2018, 22, 318. (d) Alsharif, M. A.; Khan, D.; Mukhtar, S.; Alahmdi, M. I.; Ahmed, N. Eur. J. Org. Chem. 2018, 3454. (e) Barkov, A. Yu.; Korotaev, V. Yu.; Kotovich, I. V.; Zimnitskiy, N. S.; Kutyashev, I. B.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2016, 52, 814. (f) Korotaev, V. Yu.; Sosnovskikh, V. Ya.; Kutyashev, I. B.; Kodess, M. I. Russ. Chem. Bull. 2006, 55, 317. (g) Micheletti, G.; Pollicino, S.; Ricci, A.; Berionni, G.; Cahiez, G. Synlett 2007, 2829.

  6. Rene, L. Synthesis 1989, 69.

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

    CAS  Google Scholar 

  8. (a) Osipov, D. V.; Melnikova, I. V.; Korzhenko, K. S.; Osyanin, V. A.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2020, 56, 990. (b) Osyanin, V. A.; Osipov, D. V.; Melnikova, I. V.; Korzhenko, K. S.; Semenova, I. A.; Klimochkin, Yu. N. Synthesis 2020, 3604. (c) Osyanin, V. A.; Korzhenko, K. S.; Rashchepkina, D. A.; Osipov, D. V.; Klimochkin, Yu. N. Russ. J. Org. Chem. 2021, 57, 1053. (d) Osipov, D. V.; Artyomenko, A. A.; Korzhenko, K. S.; Rashchepkina, D. A.; Demidov, O. P.; Osyanin, V. A. Russ. J. Org. Chem. 2023, 59, 422.

  9. Shriner, R. L.; Grillot, G. F.; Teeters, W. O. J. Am. Chem. Soc. 1946, 68, 946.

    Article  CAS  PubMed  Google Scholar 

  10. Mukhopadhyay, C.; Rana, S.; Butcher, R. J. Synth. Commun. 2012, 42, 3077.

    Article  CAS  Google Scholar 

  11. Bell, V. L.; Cromwell, N. H. J. Org. Chem. 1958, 23, 789.

    Article  CAS  Google Scholar 

  12. Mazzei, M.; Nieddu, E.; Miele, M.; Balbi, A.; Ferrone, M.; Fermeglia, M.; Mazzei, M. T.; Pricl, S.; La Colla, P.; Marongiu, F.; Ibba, C.; Loddo, R. Bioorg. Med. Chem. 2008, 16, 2591.

    Article  CAS  PubMed  Google Scholar 

  13. Faulques, M.; Rene, L.; Royer, R. Synthesis 1982, 260.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Vitaly A. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 249–253

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 1133 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Osipov, D.V., Artemenko, A.A., Krasnikov, P.E. et al. The synthesis of 3-nitro-4H-benzo[h]chromenes. Chem Heterocycl Comp 59, 249–253 (2023). https://doi.org/10.1007/s10593-023-03189-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03189-9

Keywords

Navigation