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Synthesis of novel 6-methyl-4-sulfanylfuro[3,4-с]pyridin-3(1H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of 6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-one in an alkaline medium proceeds regioselectively at the sulfur atom to form sulfanyl derivatives.

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References

  1. Litvinov, V. P.; Dotsenko, V. V.; Krivokolysko, S. G. Khimiya tienopiridinov i rodstvennykh system [in Russian]; Belen'kii, L. I., Ed.; Moscow: Nauka, 2006.

  2. Dotsenko, V. V.; Krivokolysko, S. G.; Semenova, A. M. Chem. Heterocycl. Compd. 2018, 54, 989. [Khim. Geterotsikl. Soedin. 2018, 989.]

  3. Hovhannisyan, A.; Pham, T. H.; Bouvier, D.; Qin, L.; Melikyan, G.; Reboud-Ravaux, M.; Bouvier-Durand, M. Bioorg. Med. Chem. Lett. 2013, 23, 2696.

    Article  CAS  Google Scholar 

  4. Hovhannisyan, A.; Pham, T. H.; Bouvier, D.; Piroyan, A.; Dufau, L.; Qin, L.; Cheng, Y.; Melikyan, G.; Reboud-Ravaux, M.; Bouvier-Durand, M. Biorg. Med. Chem. Lett. 2014, 24, 1571.

    Article  CAS  Google Scholar 

  5. Gllchrist, T. Heterocyclic Chemistry [Russian translation]; Moscow: Mir, 1996, 153.

    Google Scholar 

  6. Hong, H.; Comins, D. L. J. Org. Chem. 1996, 61, 391.

    Article  CAS  Google Scholar 

  7. Kaigorodova, E. A. Izv. vyssh. uchebn. zaved. Khim. Khim. Tekhnol. 2003, 46(8), 3. 8. Bruce, W. F.; Coover H. W., Jr. J. Am. Chem. Soc. 1944, 66, 2092.

  8. Kaigorodova, E. А.; Kvak, S. N.; Ugrak, B. I.; Zaplishnyi, V. N.; Kul'nevich, V. G. Zh. Org. Khim. 1995, 31, 1860.

    CAS  Google Scholar 

  9. Jang, Y. J.; Achary, R.; Lee, H. W.; Lee, H. J.; Lee, C.-K.; Han, S. B.; Jung, Y.-S.; Kang, N. S.; Kim, P.; Kim, M. Antiviral Res. 2014, 107, 66.

    Article  CAS  Google Scholar 

  10. Kaigorodova, E. А.; Arustamova, I. S.; Kvak, S. N.; Kul'nevich, V. G. Khimiya i tekhnologiya furanovykh soedinenii [in Russian]: Mezhvuz. sb. nauch. tr.; Krasnodar, 1997.

    Google Scholar 

  11. Kaigorodova, E. A.; Konyushkin, L. D.; Niyazymbetov, M. E.; Kvak, S. N.; Zaplishny, V. N.; Litvinov, V. P. Russ. Chem. Bull. 1994, 43, 2095. [Izv. Akad. Nauk, Ser. Khim. 1994, 2215.]

  12. Kaigorodova, E. А.; Konyushkin, L. D.; Kostenko, Е. S.; Pestunova, S. А.; Barchukova, А. Ya.; Chernysheva, N. V. RF patent 2497359; Byull. Izobret. 2013, (31).

  13. Kaigorodova, E. А.; Konyushkin, L. D.; Kostenko, Е. S.; Barchukova, А. Ya.; Chernysheva, N. V. RF patent 2495569; Byull. Izobret. 2013, (29).

  14. Kaigorodova, E. А.; Konyushkin, L. D.; Kostenko, Е. S.; Barchukova, А. Ya.; Chernysheva, N. V. RF patent 2491816; Byull. Izobret. 2013, (25).

  15. Pretsch, E.; Bühlmann, P. Structure Determination of Organic Compounds. Tables of Spectral Data [Russian translation]; Affolter, K., Ed.; Moscow: Mir, 2006.

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The study was supported by the Ministry of Agriculture of the Russian Federation (topic AAAA-A16-116021110069-8) and the Ministry of Education and Science of the Russian Federation (grant 4.6087.2017/ БЧ).

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Correspondence to Elena А. Kaigorodova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(10), 1098–1103

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Kaigorodova, E.А., Gantsgorn, N.M., Konyushkin, L.D. et al. Synthesis of novel 6-methyl-4-sulfanylfuro[3,4-с]pyridin-3(1H)-ones. Chem Heterocycl Comp 55, 1098–1103 (2019). https://doi.org/10.1007/s10593-019-02584-5

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  • DOI: https://doi.org/10.1007/s10593-019-02584-5

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