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.
Similar content being viewed by others
References
Natali, M. and Giordani, S., Chem. Soc. Rev., 2012, vol. 41, p. 4010.
Irie, M., Fukaminato, T., Matsuda, K., and Kobatake, S., Chem. Rev., 2014, vol. 114, p. 12174.
Fihey, A., Perrier, A., Browne, W.R., and Jacquemin, D., Chem. Soc. Rev., 2015, vol. 44, p. 3719.
Szymañski, W., Beierle, J.M., Kistemaker, H.A.V., Velema, W.A., and Feringa, B.L., Chem. Rev., 2013, vol. 113, p. 6114.
Huo, Z., Li, Z., Wang, T., and Zeng, H., Tetrahedron, 2013, vol. 69, p. 8964.
Ma, L., Wang, Q., Lu, G., Chen, R., and Sun, X., Langmuir, 2010, vol. 26, p. 6702.
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.
Herpt, J.T., Stuart, M.C.A., Browne, W.R., and Feringa, B.L., Chem. Eur. J., 2014, vol. 20, p. 3077.
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.
Krayushkin, M.M., Barachevsky, V.A., and Irie, M., Heteroatom Chem., 2007, vol. 18, p.557.
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
Wutz, D., Falenczyk, C., Kuzmanovic, N., and König, B., RSC Adv., 2015, vol. 5, p. 18075.
Nourmohammadian, F., Wu, T., and Branda, N.R., Chem. Commun., 2011, p. 10954.
Ohsumi, M., Hazama, M., Fukaminato, T., and Irie, M., Chem. Commun., 2008, p. 3281.
Ohsumi, M., Fukaminato, T., Hazama, M., and Irie, M., Chem. Commun., 2005, p. 3921.
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
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
Author information
Authors and Affiliations
Corresponding author
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
About this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018050196