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Three-Component Synthesis and Optical Properties of Nicotinic Acid Esters Containing Buta-1,3-dien-1,1,3-tricarbonitrile Fragment

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Abstract

Three-component synthesis of ethyl 4-aryl-2-methyl-5-cyano-6-(dicyanomethylidene)-1,6-dihydropyridine-3-carboxylates was developed consisting in the reaction of acetoacetic ester, aromatic aldehydes, and malononitrile dimer in the presence of sodium nitrite. Optical properties of synthesized compounds were investigated and it was demonstrated that they possessed intensive fluorescence in solution and in solid state with emission maxima in the yellow and green region of the visible light.

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References

  1. Sinthupoom, N., Prachayasittikul, V., Prachayasittikul, S., Ruchirawat, S., and Prachayasittikul, V., Eur. Food Res. Technol., 2015, vol. 240, p.1.

    Article  CAS  Google Scholar 

  2. Eldehna, W., Fares, M., Abdel-Aziz, M., and Abdel-Aziz, H., Molecules, 2015, vol. 20, p. 8800.

    Article  CAS  PubMed  Google Scholar 

  3. Kawazoe, Y., Shimogawa, H., Sato, A., and Uesugi, M., Angew. Chem., Int. Ed., 2011, vol. 50, p. 5478. doi 10.1002/anie.201100935

    Article  CAS  Google Scholar 

  4. Liu, W., Chen, Z., Zheng, C.-J., Liu, X.-K., Wang, K., Li, F., Dong, Y.-P., Ou, X.-M., and Zhang, X.-H., J. Mater. Chem. C, 2015, vol. 3, p. 8817.

    Article  CAS  Google Scholar 

  5. Koner, R.R., Sinha, S., Kumar, S., Nandi, C.K., and Ghosh, S., Tetrahedron Lett., 2012, vol. 53, p. 2302.

    Article  CAS  Google Scholar 

  6. Bardasov, I.N., Alekseeva, A.U., Mihailov, D.L., Ershov, O.V., Nasakin, O.E., and Tafeenko, V.A., Tetrahedron Lett., 2014, vol. 55, p. 2730.

    Article  CAS  Google Scholar 

  7. Bardasov, I.N., Alekseeva, A.U., Chunikhin, S.S., Tafeenko, V.A., and Ershov, O.V., Tetrahedron Lett., 2017, vol. 58, p. 3919.

    Article  CAS  Google Scholar 

  8. Bardasov, I.N., Alekseeva, A.U., Ershov, O.V., and Belikov, M.Yu., Tetrahedron Lett., 2015, vol. 56, p. 5434.

    Article  CAS  Google Scholar 

  9. Ershov, O.V., Bardasov, I.N., Alekseeva, A.U., Ievlev, M.Yu., and Belikov, M.Yu., Russ. J. Org. Chem., 2017, vol. 53, p. 1025. doi 10.1134/S1070428017070107

    Article  CAS  Google Scholar 

  10. Ershov, O.V. and Bardasov, I.N., Chem. Heterocycl. Compd., 2017, vol. 53, p. 1178. doi 10.1007/s10593-018-2190-5

    Article  CAS  Google Scholar 

  11. Dalton, L.R., Sullivan, P.A., and Bale, D.H., Chem. Rev., 2010, vol. 110, p.25.

    Article  CAS  PubMed  Google Scholar 

  12. Jang, S.-H., Luo, J., Tucker, N.M., Leclercq, A., Zojer, E., Haller, M.A., Kim, T.-D., Kang, J.-W., Firestone, K., Bale, D., Lao, D., Benedict, J.B., Cohen, D., Kaminsky, W., Kahr, B., Brédas, J.-L., Reid, P., Dalton, L.R., and Jen, A.K.-Y., Chem. Mater., 2006, vol. 18, p. 2982.

    Article  CAS  Google Scholar 

  13. Liu, J., Hou, W., Feng, S., Qiu, L., Liu, X., and Zhen, Z., J. Phys. Org. Chem., 2011, vol. 24, p.439.

    Article  CAS  Google Scholar 

  14. Alias, S., Andreu, R., Cerdan, M.A., Franco, S., Garin, J., Orduna, J., Pilar Romero, P., and Villacampa, B., Tetrahedron Lett., 2007, vol. 48, p. 6539. doi 10.1016/j.tetlet.2007.07.048

    Article  CAS  Google Scholar 

  15. Andreu, R., Carrasquer, L., Franco, S., Garýn, J., Orduna, J., Baroja, N.M., Alicante, R., Villacampa, B., and Allain, M., J. Org. Chem., 2009, vol. 74, p. 6647.

    Article  CAS  PubMed  Google Scholar 

  16. Parthasarathy, V., Castet, F., Pandey, R., Mongin, O., Das, P.K., and Blanchard-Desce, M., Dyes Pigm., 2016, vol. 130, p.70.

    Article  CAS  Google Scholar 

  17. Deng, G., Bo, S., Zhou, T., Huang, H., Wu, J., Liu, J., Liu, X., Zhen, Z., and Qiu, L., J. Polymer. Sci. A: Polymer. Chem., 2013, vol. 51, p. 2841.

    CAS  Google Scholar 

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015, Russia

    I. N. Bardasov, A. Yu. Alekseeva, S. S. Chunikhin & O. V. Ershov

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  1. I. N. Bardasov
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  2. A. Yu. Alekseeva
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  3. S. S. Chunikhin
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  4. O. V. Ershov
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Corresponding author

Correspondence to I. N. Bardasov.

Additional information

Original Russian Text © I.N. Bardasov, A.Yu. Alekseeva, S.S. Chunikhin, O.V. Ershov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1152–1155.

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Bardasov, I.N., Alekseeva, A.Y., Chunikhin, S.S. et al. Three-Component Synthesis and Optical Properties of Nicotinic Acid Esters Containing Buta-1,3-dien-1,1,3-tricarbonitrile Fragment. Russ J Org Chem 54, 1161–1165 (2018). https://doi.org/10.1134/S1070428018080079

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  • DOI: https://doi.org/10.1134/S1070428018080079

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