Skip to main content
SpringerLink
Log in

Synthesis of β-vinyl-substituted 4H-chromenes and [4+2] cycloaddition reactions involving them

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

β-Vinyl-substituted chromenes were obtained from 1H-benzo[f]chromene-2-carbaldehydes and 6-bromo-4H-chromene-3-carbaldehyde by the Wittig reaction. The Diels–Alder reaction of the β-vinyl-substituted chromenes with dimethyl acetylenedicarboxylate, ninhydrin, and diethyl 2,3-dicyanofumarate yielded spiro-substituted 3,10a-dihydro-2H,5H-pyrano[2,3-b]chromenes, derivatives of 7a,10-dihydro-12H-benzo[a]xanthene and 7a,8,10,12-tetrahydro-9H-benzo[a]xanthene.

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) Sosnovskikh, V. Y. SynOpen 2021, 5, 255. (b) Ghosh, C. K.; Chakraborty, A. ARKIVOC 2015, (vi), 288. (c) Chernov, N. M.; Shutov, R. V.; Potapova, A. E.; Yakovlev, E. P. Synthesis 2020, 40. (d) Kustin, R. P.; Chernov, N. M.; Shutov, R. V.; Yakovlev, I. P. Russ. J. Gen. Chem. 2022, 92, 1604.

  2. (a) Chernov, N. M.; Moroz, T. V.; Shutov, R. V.; Kuz'mich, N. N.; Shchegolev, A. E.; Sopova, M. V.; Yakovlev, I. P. Russ. J. Gen. Chem. 2019, 89, 2463. (b) Chernov, N. M.; Shutov, R. V.; Sharoyko, V. V.; Kuz'mich, N. N.; Belyakov, A. V.; Yakovlev, I. P. Eur. J. Org. Chem. 2017, 2836. (c) Chernov, N. M.; Shutov, R. V.; Sipkina, N. Yu.; Krivchun, M. N.; Yakovlev, I. P. ChemPlusChem 2021, 86, 1256.

  3. Duan, Y.; Ying, Z.; He, F.; Ying, X.; Jia, L.; Yang, G. Fitoterapia 2021, 153, 104993.

    Article  CAS  PubMed  Google Scholar 

  4. Moriyasu, M.; Nakatani, N.; Ichimaru, M.; Nishiyama, Y.; Kato, A.; Mathenge, S. G.; Juma, F. D.; Mutiso, P. B. C. J. Nat. Med. 2011, 65, 313.

    Article  CAS  PubMed  Google Scholar 

  5. Chang, Y.; Xing, L.; Sun, C.; Liang, S.; Liu, T.; Zhang, X.; Zhu, T.; Pfeifer, B. A.; Che, Q.; Zhang, G.; Li, D. J. Nat. Prod. 2020, 83, 2749.

    Article  CAS  PubMed  Google Scholar 

  6. Ali, M.; Sahrawat, I.; Singh, O. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43B, 2217.

  7. Joolakanti, H. B.; Battu, S.; Kamepalli, R.; Kolanupaka, H. R.; Bobbili, H. R. Chem. Data Collect. 2021, 32, 100651.

    Article  CAS  Google Scholar 

  8. Kumar, S.; Singh, B. K.; Pandey, A. K.; Kumar, A.; Sharma, S. K.; Raj, H. G.; Prasad, A. K.; Eycken, E. V.; Parmar, V. S.; Ghosh, B. Bioorg. Med. Chem. 2007, 15, 2952.

    Article  CAS  PubMed  Google Scholar 

  9. Chand, K.; Tiwari, R. K.; Kumar, S.; Shirazi, A. N.; Sharma, S.; Eycken, E. V.; Parmar, V. S.; Parang, K.; Sharma, S. K. J. Heterocycl. Chem. 2015, 52, 562.

    Article  CAS  Google Scholar 

  10. Lu, K.; Zhang, Y.; Li, L.; Wang, X.; Ding, G. Molecules 2013, 18, 10944.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. (a) Osyanin, V. A.; Semenova, I. A.; Groshev, A. G.; Osipov, D. V.; Klimochkin, Yu. N. Mendeleev Commun. 2021, 31, 859. (b) Diaz, P.; Gendre, F.; Stella, L.; Charpentier, B. Tetrahedron 1998, 54, 4579. (c) Gorobets, E.; Parvez, M.; Keay, B. A. Synlett 2008, 129.

  12. (a) Osipov, D. V.; Korzhenko, K. S.; Osyanin, V. A.; Krasnikov, P. E.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2022, 58, 651. (b) Osyanin, V. A.; Osipov, D. V.; Korzhenko, K. S.; Demidov, O. P.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2021, 57, 305. (c) Osyanin, V. A.; Osipov, D. V.; Korzhenko, K. S.; Demidov, O. P.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2021, 57, 588. (d) Osipov, D. V.; Osyanin, V. A.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2018, 54, 1121. (e) Semenova, I. A.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2021, 57, 691. (f) Semenova, I. A.; Osipov, D. V.; Popova, Yu. V.; Osyanin, V. A.; Demidov, O. P.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2020, 56, 1218. (g) Osyanin, V. A.; Osipov, D. V.; Semenova, I. A.; Korzhenko, K. S.; Lukashenko, A. V.; Demidov, O. P.; Klimochkin, Yu. N. RSC Adv. 2020, 10, 34344.

  13. Das, S.; Dutta, A. ChemistrySelect 2020, 5, 11361.

    Article  CAS  Google Scholar 

  14. (a) Schönberg, A.; Singer, E. Chem. Ber. 1971, 104, 160.

    Article  Google Scholar 

  15. (b) Panda, P.; Nayak, S.; Sahoo, S. Ku.; Mohapatra, S.; Nayak, D.; Pradhan, R.; Kundu, C. N. RSC Adv. 2018, 8, 16802. (c) Gill, G. B.; Idris, M. S. Hj.; Kirollos, K. S. J. Chem. Soc., Perkin Trans. 1 1992, 2355. (d) Kumar, V.; Bell, M. R.; Wetzel, J. R.; Herrmann, J. L.; McGarry, R.; Schane, H. P.; Winneker, R. C.; Snyder, B. W.; Anzalone, A. J. J. Med. Chem. 1993, 36, 3278. (e) Lehmler, H.-J.; Nieger, M.; Breitmaier, E. Synthesis 1996, 105. (f) Schmidt, R. R.; Vogt, K. Synthesis 1983, 799. (g) Zhao, L.; Yucel, B.; Scheurich, R.-P.; Frank, D.; de Meijere, A. Chem.–Asian J. 2007, 2, 273.

  16. Lukashenko, A. V.; Osyanin, V. A.; Osipov, D. V.; Klimochkin, Yu. N. Chem. Heterocycl. Compd. 2016, 52, 711.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Samara State Technical University, 244 Molodogvardeyskaya, Samara, 443100, Russia

    Irina A. Semenova, Dmitry V. Osipov, Pavel E. Krasnikov, Vitaly A. Osyanin & Yuri N. Klimochkin

Authors
  1. Irina A. Semenova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dmitry V. Osipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pavel E. Krasnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Vitaly A. Osyanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yuri N. Klimochkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Dmitry V. Osipov or Vitaly A. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 260–266

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 3900 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

Semenova, I.A., Osipov, D.V., Krasnikov, P.E. et al. Synthesis of β-vinyl-substituted 4H-chromenes and [4+2] cycloaddition reactions involving them. Chem Heterocycl Comp 59, 260–266 (2023). https://doi.org/10.1007/s10593-023-03191-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03191-1

Keywords

Search

Navigation