Skip to main content
Log in

Synthesis of New Photochromic Dithienylmaleimides with Acetal and Aldehyde Fragments

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Reaction of 3,4-dithienylmaleic anhydrides with aminoacetaldehyde dimethylacetal results in the formation of 3,4-dithienyl-substituted 1-(2,2-dimethoxyethyl)-1H-pyrrole-2,5-diones. The hydrolysis of the latter in acid medium results in the preparation of 2-[3,4-bis(thienyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl]-acetaldehydes. The obtained functionalized derivatives of maleimide demonstrate photochromic properties in solution.

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.

Similar content being viewed by others

References

  1. Natali, M. and Giordani, S., Chem. Soc. Rev., 2012, vol. 41, p. 4010.

    Article  CAS  Google Scholar 

  2. Irie, M., Fukaminato, T., Matsuda, K., and Kobatake, S., Chem. Rev., 2014, vol. 114, p. 12174.

    Article  CAS  PubMed  Google Scholar 

  3. Fihey, A., Perrier, A., Browne, W.R., and Jacquemin, D., Chem. Soc. Rev., 2015, vol. 44, p. 3719.

    Article  CAS  PubMed  Google Scholar 

  4. Szymañski, W., Beierle, J.M., Kistemaker, H.A.V., Velema, W.A., and Feringa, B.L., Chem. Rev., 2013, vol. 113, p. 6114.

    Article  CAS  PubMed  Google Scholar 

  5. Huo, Z., Li, Z., Wang, T., and Zeng, H., Tetrahedron, 2013, vol. 69, p. 8964.

    Article  CAS  Google Scholar 

  6. Ma, L., Wang, Q., Lu, G., Chen, R., and Sun, X., Langmuir, 2010, vol. 26, p. 6702.

    Article  CAS  PubMed  Google Scholar 

  7. Indelli, M.T., Carli, S., Ghirotti, M., Chiorboli, C., Ravaglia, M., Garavelli, M., and Scandola, F., J. Am. Chem. Soc., 2008, vol. 130, p. 7286.

    Article  CAS  PubMed  Google Scholar 

  8. Herpt, J.T., Stuart, M.C.A., Browne, W.R., and Feringa, B.L., Chem. Eur. J., 2014, vol. 20, p. 3077.

    Article  CAS  PubMed  Google Scholar 

  9. Shirinian, V.Z., Shimkin, A.A., Mailian, A.K., Tsyganov, D.V., Popov, L.D., and Krayushkin, M.M., Dyes Pigm., 2010, vol. 84, p.19.

    Article  CAS  Google Scholar 

  10. Krayushkin, M.M., Barachevsky, V.A., and Irie, M., Heteroatom Chem., 2007, vol. 18, p.557.

    Article  CAS  Google Scholar 

  11. Belikov, M.Yu., Ievlev, M.Yu., Fedoseev, S.V., and Ershov, O.V., Russ. J. Org. Chem., 2017, vol. 53, p. 141. doi 10.1134/S1070428017010286

    Article  CAS  Google Scholar 

  12. Wutz, D., Falenczyk, C., Kuzmanovic, N., and König, B., RSC Adv., 2015, vol. 5, p. 18075.

    Article  CAS  Google Scholar 

  13. Nourmohammadian, F., Wu, T., and Branda, N.R., Chem. Commun., 2011, p. 10954.

    Google Scholar 

  14. Ohsumi, M., Hazama, M., Fukaminato, T., and Irie, M., Chem. Commun., 2008, p. 3281.

    Google Scholar 

  15. Ohsumi, M., Fukaminato, T., Hazama, M., and Irie, M., Chem. Commun., 2005, p. 3921.

    Google Scholar 

  16. Krayushkin, M.M., Yarovenko, V.N., Semenov, S. L., Zavarzin, I.V., Martynkin, A.Yu., and Uzhinov, B.M., Russ. Chem. Bull., 2003, vol. 52, p. 1814. doi 10.1023/A:1026069007586

    Article  CAS  Google Scholar 

  17. Kuznetsova, O.Yu., Platonova, I.V., Lichitskii, B.V., Krayushkin, M.M., and Barachevskii, V.A., Russ. Chem. Bull., 2012, vol. 61, p. 2109. doi 10.1007/s11172-012-0295-z

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to М. Yu. Belikov.

Additional information

Original Russian Text © M.Yu. Belikov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 5, pp. 780–783.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Belikov, М.Y. Synthesis of New Photochromic Dithienylmaleimides with Acetal and Aldehyde Fragments. Russ J Org Chem 54, 785–788 (2018). https://doi.org/10.1134/S1070428018050196

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018050196

Navigation