Skip to main content

Advertisement

SpringerLink
Log in

Cyclopropanation of areno-condensed 4H-pyrans with dihalocarbenes

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The addition of dihalocarbenes to 1H-benzo[f]chromenes and 4H-chromenes gave a number of dihalotetrahydro(benzo)cyclopropa[b]-chromenes containing donor and acceptor substituents at different positions. It was found that in the case of 1,3-disubstituted 1H-benzo[f]-chromenes, the reaction proceeds diastereoselectively with the formation of trans-isomers. 12H,13H-7a,12a-Methanobenzo[f]indeno-[1,2-b]chromene and 12,13-dihydro-14H-7a,13a-methanodibenzo[a,h]xanthene, representatives of new heterocyclic systems, were obtained.

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) Thankachan, A. P.; Sindhu, K. S.; Krishnan, K. K.; Anilkumar, G. Org. Biomol. Chem. 2015, 13, 8780. (b) Cousins, G. S.; Hoberg, J. O. Chem. Soc. Rev. 2000, 29, 165. (c) Fedorynski, M. Chem. Rev. 2003, 103, 1099. (d) Doblier, W. R.; Battiste, M. A. Chem. Rev. 2003, 103, 1071. (e) Harvey, J. E.; Hewitt, R. J.; Moore, P. W.; Somarathne, K. K. Pure Appl. Chem. 2014, 86, 1377.

  2. (a) Hewitt, R. J.; Harvey, J. E. J. Org. Chem. 2010, 75, 955. (b) Ganesh, N. V.; Jayaraman, N. J. Org. Chem. 2009, 74, 739. (c) Ganesh, N. V.; Jayaraman, N. J. Org. Chem. 2007, 72, 5500. (d) Moore, P. W.; Schuster, J. K.; Hewitt, R. J.; Stone, M. R. L.; Teesdale-Spittle, P. H.; Harvey, J. E. Tetrahedron 2014, 70, 7032. (e) Ramana, C. V.; Murali, R.; Nagarajan, M. J. Org. Chem. 1997, 62, 7694. (f) Dey, S.; Jayaraman, N. Carbohydr. Res. 2014, 399, 49. (g) Dey, S.; Jayaraman, N. Carbohydr. Res. 2014, 389, 66.

  3. (a) Schweizer, E. E.; Parham, W. E. J. Am. Chem. Soc. 1960, 82, 4085. (b) Parham, W. E.; Huestis, L. D. J. Am. Chem. Soc. 1962, 84, 813. (c) Koblik, A. V.; Suzdalev, K. F.; Loktionov, A. A. Chem. Heterocycl. Compd. 1987, 23, 155. [Khim. Geterotsikl. Soedin. 1987, 188.]

  4. Hewitt, R. J.; Harvey, J. E. Chem. Commun. 2011, 421.

  5. Murali, R.; Ramana, C. V.; Nagarajan, M. J. Chem. Soc., Chem. Commun. 1995, 217.

  6. Lin, H.; Yang, M.; Huang, P.; Cao, W. Molecules 2003, 8, 608.

    Article  CAS  Google Scholar 

  7. (a) Duggan, A. J.; Hall, S. S. J. Org. Chem. 1975, 40, 2234. (b) Parham, W. E.; Huestis, L. D. J. Am. Chem. Soc. 1962, 84, 813.

  8. (a) Sacquet, M.-C.; Graffe, B.; Maitte, P. Bull. Soc. Chim. Fr. 1971, 2557. (b) Koblik, A. V.; Suzdalev, K. F.; Dorofeenko, G. N. Chem. Heterocycl. Compd. 1982, 18, 124. [Khim. Geterotsikl. Soedin. 1982, 163.] (c) Kostikov R. R.; Molchanov, А. P.; Suzdalev, K. F.; Koblik, А. V. Zh. Org. Khim. 1990, 26, 355.

  9. Rotzoll, S.; Appel, B.; Langer, P. Tetrahedron Lett. 2005, 46, 4057.

    Article  CAS  Google Scholar 

  10. Flavonoids: Chemistry, Biochemistry and Applications; Andersen, Ø. M., Markham, K. R., Eds.; Taylor & Francis, 2006, p. 1197.

  11. El-Kouhen, O.; Lehto, S. G.; Pan, J. B.; Chang, R.; Baker, S. J.; Zhong, C.; Hollingsworth, P. R.; Mikusa, J. P.; Cronin, E. A.; Chu, K. L.; McGaraughty, S. P.; Uchic, M. E.; Miller, L. N.; Rodell, N. M.; Patel, M.; Bhatia, P.; Mezler, M.; Kolasa, T.; Zheng, G. Z.; Fox, G. B.; Stewart, A. O.; Decker, M. W.; Moreland, R. B.; Brioni, J. D.; Honore, P. Br. J. Pharmacol. 2006, 149, 761.

    Article  CAS  Google Scholar 

  12. Xue, H.; Lu, X.; Zheng, P.; Liu, L.; Han, C.; Hu, J.; Liu, Z.; Ma, T.; Li, Y.; Wang, L.; Chen, Z.; Liu, G. J. Med. Chem. 2010, 53, 1397.

    Article  CAS  Google Scholar 

  13. Spasov, A. A.; Babkov, D. A.; Osipov, D. V.; Klochkov, V. G.; Prilepskaya, D. R.; Demidov, M. R.; Osyanin, V. A.; Klimochkin, Yu. N. Bioorg. Med. Chem. Lett. 2019, 29, 119.

    Article  CAS  Google Scholar 

  14. (a) Bessard, Y.; Müller, U.; Schlosser, M. Tetrahedron 1990, 46, 5213. (b) Bychek, R. M.; Levterov, V. V.; Sadkova, I. V.; Tolmachev, A. A.; Mykhailiuk, P. K. Chem.–Eur. J. 2018, 24, 12291. (c) Saito, A.; Okada, M.; Nakamura, Y.; Kitagawa, O.; Horikawa, H.; Taguchi, T. J. Fluorine Chem. 2003, 119, 75.

  15. Demidov, М. R. PhD Thesis in Chemistry, Samara, 2019.

  16. (a) Corsaro, A.; Chiacchio, U.; Adamo, R.; Pistarà, V.; Rescifina, A.; Romeo, R.; Catelani, G.; D’Andrea, F.; Mariani, M.; Attolino, E. Tetrahedron 2004, 60, 3787. (b) Banwell, M. G.; Lambert, J. N.; Gulbis, J. M.; Mackay, M. F. J. Chem. Soc., Chem. Commun. 1990, 1450. (c) Billups, W. E.; Reed, L. E.; Casserly, E. W.; Lin, L. P. J. Org. Chem. 1981, 46, 1326. (d) Kim, H. Y.; Salvi, L.; Carroll, P. J.; Walsh, P. J. J. Am. Chem. Soc. 2009, 131, 954.

  17. Osyanin, V. А.; Demidov, М. R.; Osipov, D. V.; Klimochkin, Yu. N. RF patent № 2597363.

Download references

This work was supported by the Russian Science Foundation (grant 19-13-00421).

Author information

Authors and Affiliations

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

    Irina А. Semenova, Vitaly А. Osyanin, Maxim R. Demidov, Dmitry V. Osipov & Yuri N. Klimochkin

Authors
  1. Irina А. Semenova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vitaly А. Osyanin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maxim R. Demidov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Dmitry V. Osipov
    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 author

Correspondence to Vitaly А. Osyanin.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(11), 1417–1422

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Semenova, I.А., Osyanin, V.А., Demidov, M.R. et al. Cyclopropanation of areno-condensed 4H-pyrans with dihalocarbenes. Chem Heterocycl Comp 56, 1417–1422 (2020). https://doi.org/10.1007/s10593-020-02831-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02831-0

Keywords

Search

Navigation