Skip to main content
SpringerLink
Log in

Photocycloaddition reaction of methyl 2- and 3-chromonecarboxylates with various alkenes

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

The irradiation of methyl 2- and 3-chromonecarboxylate in the presence of various alkenes afforded cyclobutane type adducts, whose structures were established by X-ray structural analysis. Methyl 2-chromonecarboxylate showed higher photochemical reactivity than methyl 3-chromonecarboxylate, in which endo adducts were yielded as major products.

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

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. J. Conrad, B. Forster-Fromme, M.-A. Constantin, V. Ondrus, S. Mika, F. Mert-Balci, I. Klaiber, J. Pfannstiel, W. Moller, H. Rosner, K. Forster-Fromme, U. Beifuss, J. Nat. Prod. 72, 835–840 (2009)

    Article  CAS  Google Scholar 

  2. B.H. Havsteen, Pharmacol. Ther. 96, 67–202 (2002)

    Article  CAS  Google Scholar 

  3. N. Okamura, N. Hine, S. Harada, T. Fujika, K. Mihashi, A. Yagi, Phytochemistry 43, 495–498 (1996)

    Article  CAS  Google Scholar 

  4. G. Speranza, C.F. Morelli, A. Tubaro, G. Altinier, L. Durì, P. Manitto, Planta Med. 71, 79–81 (2005)

    Article  CAS  Google Scholar 

  5. A. Yagi, A. Kabash, N. Okamura, H. Haraguchi, S.M. Moustafa, T.I. Khalifa, Planta Med. 68, 957–960 (2002)

    Article  CAS  Google Scholar 

  6. M. Mazzei, E. Sottofattori, R. Dondero, M. Ibrahim, E. Melloni, M. Michetti, Farmaco 54, 452–460 (1999)

    Article  CAS  Google Scholar 

  7. A. Nath, A. Ghosh, R.V. Venkateswaran, J. Org. Chem. 57, 1467–1472 (1992)

    Article  CAS  Google Scholar 

  8. J.W. Hanifin, E. Cohen, J. Am. Chem. Soc. 91, 4494–4499 (1969)

    Article  CAS  Google Scholar 

  9. J.W. Hanifin, E. Cohen, Tetrahedron Lett. 7, 5421–5426 (1966)

    Article  Google Scholar 

  10. J.W. Hanifin, G.O. Morton, Tetrahedron Lett. 8, 2307–2311 (1967)

    Article  Google Scholar 

  11. A. Nath, A. Ghosh, R.V. Venkateswaran, J. Org. Chem. 57, 1467–1472 (1992)

    Article  CAS  Google Scholar 

  12. T. Matsui, M. Nakayama, Bull. Chem. Soc. Jpn. 56, 3531–3532 (1983)

    Article  CAS  Google Scholar 

  13. M. Sakamoto, M. Kanehiro, T. Mino, T. Fujita, Photodimerization of a simple chromone leading to anti-HT and cis-trans-HT dimers in low quantum efficiency. Chem. Commun. 17, 2379–2380 (2009)

    Article  Google Scholar 

  14. P. Mandal, A. Nath, R.V. Venkateswaran, Photodimerization of 3-methoxychromone derivatives subsequently followed by Norrish type II reaction, in which the stereochemistry and the details are ambiguous. Tetrahedron 52, 7855–7860 (1996)

    Article  CAS  Google Scholar 

  15. S.C. Gupta, S.K. Mukerjee, Tetrahedron Lett. 14, 5073–5074 (1973)

    Article  Google Scholar 

  16. M. Sakamoto, F. Yagishita, M. Kanehiro, Y. Kasashima, T. Mino, T. Fujita, Org. Lett. 12, 4435–4437 (2010)

    Article  CAS  Google Scholar 

  17. K. Wakasugi, T. Misaki, K. Yamada, Y. Tanabe, Tetrahedron Lett. 41, 5249–5250 (2000)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by a Grant-in-Aid for Scientific Research (No 21350024, 20655007) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of the Japanese Government.

Author information

Authors and Affiliations

  1. Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan

    Masami Sakamoto, Kazuya Yoshiwara, Fumitoshi Yagishita, Wataru Yoshida, Takashi Mino & Tsutomu Fujita

Authors
  1. Masami Sakamoto
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Kazuya Yoshiwara
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fumitoshi Yagishita
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wataru Yoshida
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Takashi Mino
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tsutomu Fujita
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Masami Sakamoto.

Additional information

This article is published as part of a themed issue in honor of Prof. Kazuhiko Mizuno’s research accomplishments on the occasion of his retirement.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sakamoto, M., Yoshiwara, K., Yagishita, F. et al. Photocycloaddition reaction of methyl 2- and 3-chromonecarboxylates with various alkenes. Res Chem Intermed 39, 385–395 (2013). https://doi.org/10.1007/s11164-012-0656-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0656-0

Keywords

Search

Navigation