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Synthesis and Luminescent Properties of 3-Acyl-6,8,8,9-tetramethyl-2H-pyrano[3,2-g]hydroquinolin-2-ones

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Abstract

A series of 3-R-6,8,8,9-tetramethyl-2H-pyrano[3,2-g]quinolin-2-ones was obtained by condensation of 7-hydroxy-1,2,2,4-tetramethylhydroquinoline-6-carbaldehydes with aroylacetic acid esters. The dependence of the UV and photoluminescence spectra on the structure of the obtained compounds was studied.

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REFERENCES

  1. Li, C., Nat. Mater., 2014, vol. 13, p. 110. https://doi.org/10.1038/nmat3877

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Kooreman, N.G., Ransohoff, J.D., and Wu, J.C., Nat. Mater., 2014, vol. 13, p. 106. https://doi.org/10.1038/nmat3868

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Reynolds, G.A. and Drexhage, K.-H., Opt. Commun., 1975, vol. 13, p. 222. https://doi.org/10.1016/0030-4018(75)90085-1

    Article  CAS  Google Scholar 

  4. Jones, G.II, Jackson, W.R., and Halpern, A.M., Chem. Phys. Lett., 1980, vol. 72, p. 391. https://doi.org/10.1016/0009-2614(80)80314-9

    Article  CAS  Google Scholar 

  5. Corrie, J.E.T., Munasinghe, V.R.N., and Rettig, W., J. Heterocycl. Chem., 2000, vol. 37, p. 1447. https://doi.org/10.1002/jhet.5570370608

    Article  CAS  Google Scholar 

  6. Murata, C., Masuda, T., Kamochi, Y., Todoroki, K., Yoshida, H., Nohta, H., Yamaguchi, M., and Takadate, A., Chem. Pharm. Bull., 2005, vol. 53, p. 750. https://doi.org/10.1248/cpb.53.750

    Article  CAS  PubMed  Google Scholar 

  7. Zhang, X., Zhang, J.-J., and Xia, Y.-Y., J. Photochem. Photobiol., 2008, vol. 194, p. 167. https://doi.org/10.1016/j.jphotochem.2007.08.004

    Article  CAS  Google Scholar 

  8. Lin, Q., Bao, C., Fan, G., Cheng, S., Liu, H., Liu, Z., and Zhu, L., J. Mater. Chem., 2012, vol. 22, p. 6680. https://doi.org/10.1039/c2jm33364c

    Article  CAS  Google Scholar 

  9. Ni, X., Guo, Y., Bu, H., An, J., and En, D., J. Chin. Chem. Soc., 2012, vol. 59, p. 1439. https://doi.org/10.1002/jccs.201200010

    Article  CAS  Google Scholar 

  10. Schiedel, M.-S., Briehn, C.A., and Bauerle, P., Angew. Chem., 2001, vol 113, p. 4813. https://doi.org/10.1002/1521-3757(20011217)113:24<4813:AID-ANGE4813>3.0.CO;2-T

  11. Nagy, K., Orban, E., Bзsze, S., and Kele, P., Chem. Asian J., 2010, vol. 5, p. 773. https://doi.org/10.1002/asia.200900477

    Article  CAS  PubMed  Google Scholar 

  12. Sun, Y.-Q., Liu, J., Zhang, J., Yang, T., and Guo, W., Chem. Commun., 2013, vol. 49, p. 2637. https://doi.org/10.1039/C3CC39161B

    Article  CAS  Google Scholar 

  13. Richard, J.-A., Massonneau, M., Renard, P.-Y., and Romieu, A., Org. Lett., 2008, vol. 10, p. 4175. https://doi.org/10.1021/ol801582w

    Article  CAS  PubMed  Google Scholar 

  14. Huang, H.-C., Wang, K.-L., Huang, S.-T., Lin, H.-Y., and Lin, C.-M., Biosens. Bioelectron., 2011, vol. 26, p. 3511. https://doi.org/10.1016/j.bios.2011.01.036

    Article  CAS  PubMed  Google Scholar 

  15. Cao, X., Lin, W., Yu, Q., and Wang, J., Org. Lett., 2011, vol. 13, p. 6098. https://doi.org/10.1021/ol202595t

    Article  CAS  PubMed  Google Scholar 

  16. Hara, K., Sato, T., Katoh, R., Furube, A., Ohga, Y., Shinpo, A., Suga, S., Sayama, K., Sugihara, H., and Arakawa, H., J. Phys. Chem. B, 2003, vol. 107, p. 597. https://doi.org/10.1021/jp026963x

    Article  CAS  Google Scholar 

  17. Hara, K., Dan-oh, Y., Kasada, C., Ohga, Y., Shinpo, A., Suga, S., Sayama, K., and Arakawam, H., Langmuir, 2004, vol. 20, p. 4205. https://doi.org/10.1021/la0357615

    Article  CAS  PubMed  Google Scholar 

  18. Wang, Z.-S., Cui, Y., Dan-oh, Y., Kasada, C., Shinpo, A., and Hara, K., J. Phys. Chem. (C), 2007, vol. 111, p. 7224. https://doi.org/10.1021/jp067872t

  19. Wang, Z.-S., Dan-oh, Y.C.Y., Kasada, C., Shinpo, A., and Hara, K., J. Phys. Chem. (C), 2008, vol. 112, p. 17011. https://doi.org/10.1021/jp067872t

    Article  CAS  Google Scholar 

  20. Nizamov, S., Willig, K.I., Sednev, M.V., Belov, V.N., and Hell, S.W., Chem. Eur. J., 2012, vol. 18, p. 16339. https://doi.org/10.1002/chem.201202382

    Article  CAS  PubMed  Google Scholar 

  21. Schill, H., Nizamov, S., Bottanelli, F., Bierwagen, J., Belov, V.N., and Hell, S.W., Chem. Eur. J., 2013, vol. 19, p. 16556. https://doi.org/10.1002/chem.201302037

    Article  CAS  PubMed  Google Scholar 

  22. Manahelohe, G.M., Potapov, A.Yu., and Shikhaliev, Kh.S., Russ. Chem. Bull., 2016, no. 4, p. 1145. https://doi.org/10.1007/s11172-016-1427-7

    Article  CAS  Google Scholar 

  23. Danish, Kh., Sayeed, M., Meshari, A.A., and Mohammed, I.A., Tetrahedron Lett., 2017, vol. 58, p. 3183. https://doi.org/10.1016/j.tetlet.2017.07.018

    Article  CAS  Google Scholar 

  24. Ranjith, Ch., Paul, N., and Vijayan, K.K., Asian J. Chem., 2011, vol. 23, p. 235.

    CAS  Google Scholar 

  25. Verdia, P., Santamarta, F., and Tojo, E., Molecules, 2011, vol. 16, p. 4379. https://doi.org/10.3390/molecules16064379

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. He, X., Shang, Y., Zhou, Y., Yu, Zh., Han, G., Jin, W., and Chen, J., Tetrahedron, 2015, vol. 71, p. 863. https://doi.org/10.1016/j.tet.2014.12.042

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Russian Foundation for Basic Research (project no. 18-74-10097).

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Correspondence to A. Yu. Potapov.

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Potapov, A.Y., Vandyshev, D.Y., Refki, Y. et al. Synthesis and Luminescent Properties of 3-Acyl-6,8,8,9-tetramethyl-2H-pyrano[3,2-g]hydroquinolin-2-ones. Russ J Gen Chem 90, 1216–1221 (2020). https://doi.org/10.1134/S1070363220070075

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