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Synthesis of Substituted 4-(Thiophen-2-yl)nicotinonitriles

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Abstract

A series of 4-(thiophen-2-yl)-substituted nicotinonitriles were prepared by a three step procedure including condensation and cyclization of 2-acetylthiophene. A more efficient synthesis of the target products is proposed and the transformation of some of the synthesized nicotinonitrles into 1H-pyrazolo[3,4-b]pyridines is described.

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REFERENCES

  1. Perrier, V., Wallace, A.C., Kaneko, K., Safar, J., Prusiner, S.B., and Cohen, F.E., Proc. Natl. Acad.Sci., 2000, vol. 97, p. 6073. https://doi.org/10.1073/pnas.97.11.6073

    Article  CAS  PubMed  Google Scholar 

  2. Guo, K., Mutter, R., Heal, W., Reddy, T.R.K., Cope, H., Pratt, S., Thompson, M.J., and Chen, B., Eur. J. Med.Chem., 2008, vol. 43, p. 93. https://doi.org/10.1016/j.ejmech.2007.02.018

    Article  CAS  PubMed  Google Scholar 

  3. Cateni, F., Zacchigna, M., Pedemonte, N., Galietta, L.J.V., Mazzei, M.T., Fossa, P., Giampieri, M., and Mazzei, M., Bioorg. Med. Chem., 2009, vol. 17, p. 7894. https://doi.org/10.1016/j.bmc.2009.10.028

    Article  CAS  PubMed  Google Scholar 

  4. Liu, B., Bao, Y., Du, F., Wang, H., Tiana, J., and Bai, R., Chem. Commun., 2011, vol. 47, p. 1731. https://doi.org/10.1039/c0cc03819a

    Article  CAS  Google Scholar 

  5. Hakobyan, R.M., Russ. J. Org. Chem., 2019, vol. 55, p. 1238. https://doi.org/10.1134/S1070428019080268

    Article  CAS  Google Scholar 

  6. Hakobyan, R.M., Hayotsyan, S.S., Attaryan, H.S., and Melikyan, G.S., Chem. Heterocycl. Comp., 2019, vol. 55, p. 1245. https://doi.org/10.1007/s10593-019-02608-0

    Article  CAS  Google Scholar 

  7. Cheikh, N., Villemin, D., Bar, N, Lohier, J.-F., ChoukchouBraham, N., Mostefa-Kara, B., and Sopkova, J., Tetraherdon, 2013, vol. 69, p. 1234. https://doi.org/10.1016/j.tet.2012.10.108

    Article  CAS  Google Scholar 

  8. Villemin, D., Belhadj, Z., Cheikh, N., Choukchou-Braham, N., Bar, N., and Lohier, J.-F., TetrahedronLett., 2013, vol. 54, p. 1664. https://doi.org/10.1016/j.tetlet.2013.01.021

    Article  CAS  Google Scholar 

  9. Ibrahim, H.M., Behbehani, H., and Mostafa, N.S., ACS Omega, 2019, vol. 4, p. 7182. https://doi.org/10.1021/acsomega.9b00562

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Barnes, D.M., Haight, A.R., Hameury, T., McLaughlin, M.A., Mei, J., Tedrow, J.S., and Toma, J.D.R., Tetraherdon, 2006, vol. 62, p. 11311. https://doi.org/10.1016/j.tet.2006.07.008

    Article  CAS  Google Scholar 

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Funding

The work was financially supported by the Committee for Education, Science and Sports of the Republic of Armenia (grant no. 18T-2E151).

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Correspondence to S. S. Hayotsyan.

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Hakobyan, R.M., Attaryan, H.S., Melikyan, G.S. et al. Synthesis of Substituted 4-(Thiophen-2-yl)nicotinonitriles. Russ J Org Chem 56, 356–360 (2020). https://doi.org/10.1134/S1070428020020323

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  • DOI: https://doi.org/10.1134/S1070428020020323

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