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Chemistry of Iminofurans: XV. Decyclization of Ethyl 2-[5-Aryl-2-oxofuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylates by the Action of Secondary Amines

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Abstract

Ethyl 2-[5-aryl-2-oxofuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylates reacted with secondary amines to give 4-aryl-2-(thiophen-2-yl)-4-oxobutanamides, whereas their reaction with piperazine afforded N,N′-disubstituted piperazine derivatives regardless of the reactant ratio.

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References

  1. Kiselev, M.A., Igidov, N.M., Chernov, I.N., Toksarova, Yu.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2017, vol. 53, p. 920.

    Article  CAS  Google Scholar 

  2. Zalesov, V.V. and Rubtsov, A.E., Chem. Heterocycl. Compd., 2004, vol. 40, p. 133.

    Article  CAS  Google Scholar 

  3. Rubtsov, A.E. and Zalesov, V.V., Russ. J. Org. Chem., 2003, vol. 39, p. 869.

    Article  CAS  Google Scholar 

  4. Igidov, N.M., Rubtsov, A.E., Tyuneva, A.V., Zalesov, V.V., Borodin, A.Yu., and Bukanova, E.V., Russ. J. Org. Chem., 2009, vol. 45, p. 698.

    Article  CAS  Google Scholar 

  5. Tyuneva, A.V., Igidov, N.M., Koryagina, N.N., Borodin, A.Yu., Zakhmatov, A.V., Makarov, A.S., Toksarova, Yu.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2011, vol. 47, p. 258.

    Article  CAS  Google Scholar 

  6. Shipilovskikh, S.A., Rubtsov, A.E., and Zalesov, V.V., Chem. Heterocycl. Compd., 2009, vol. 45, p. 658.

    Article  CAS  Google Scholar 

  7. Igidov, N.M., Kiselev, M.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2016, vol. 52, p. 526.

    Article  CAS  Google Scholar 

  8. Komarova, O.A., Igidov, N.M., Koryagina, N.N., Makarov, A.S., Toksarova, Yu.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2011, vol. 47, p. 109.

    Article  CAS  Google Scholar 

  9. Pulina, N.A., Kuznetsov, A.S., and Rubtsov, A.E., Russ. J. Org. Chem., 2015, vol. 51, p. 967.

    Article  CAS  Google Scholar 

  10. Komarova, O.A., Igidov, N.M., Rubtsov, A.E., Zalesov, V.V., Makarov, A.S., and Toksarova, Yu.S., Russ. J. Org. Chem., 2010, vol. 46, p. 236.

    Article  CAS  Google Scholar 

  11. Shipilovskikh, S.A. and Rubtsov, A.E., Russ. Chem. Bull., Int. Ed., 2014, vol. 63, p. 2205.

    Article  CAS  Google Scholar 

  12. Kharitonova, S.S., Igidov, N.M., Zakhmatov, A.V., and Rubtsov, A.E., Russ. J. Org. Chem., 2013, vol. 49, p. 243.

    Article  CAS  Google Scholar 

  13. Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Org. Chem., 2014, vol. 50, p. 1853.

    Article  CAS  Google Scholar 

  14. Shipilovskikh, S.A. and Rubtsov, A.E., Russ. J. Org. Chem., 2014, vol. 50, p. 298.

    Article  CAS  Google Scholar 

  15. Rubtsov, A.E. and Zalesov, V.V., Russ. J. Org. Chem., 2007, vol. 43, p. 735.

    Article  CAS  Google Scholar 

  16. Rubtsov, A.E., Aliev, Z.G., and Maiorova, O.A., Russ. J. Org. Chem., 2010, vol. 46, p. 933.

    Article  CAS  Google Scholar 

  17. Zalesov, V.V., Bystritskaya, O.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2007, vol. 43, p. 1415.

    Article  CAS  Google Scholar 

  18. Pulina, N.A., Sobin, F.V., Kozhukhar’, V.Yu., Makhmudov, R.R., Rubtsov, A.E., and Naugol’nykh, E.A., Pharm. Chem. J., 2014, 48, no. 1, p. 11.

    Article  CAS  Google Scholar 

  19. Pulina, N.A., Zalesov, V.V., Bystritskaya, O.A., Rubtsov, A.E., and Kutkovaya, N.V., Pharm. Chem. J., 2009, vol. 43, no. 8, p. 444.

    Article  CAS  Google Scholar 

  20. Bello Forero, J.S., Jones, J., Jr., and Silva, F.M., Curr. Org. Synth., 2013, vol. 10, p. 347.

    Article  CAS  Google Scholar 

  21. Puterová, Z., Krutošíková, A., and Végh, D., Nova Biotechnol., 2009, vol. 9, no. 2, p. 167.

    Google Scholar 

  22. Puterová, Z., Krutošíková, A., and Végh, D., Arkivoc, 2010, part (i), p. 209.

    Google Scholar 

  23. Shipilovskikh, S.A., Makhmudov, R.R., Lupach, D.Yu., Pavlov, P.T., Babushkina, E.V., and Rubtsov, A.E., Pharm. Chem. J., 2013, vol. 47, no. 7, p. 366.

    Article  CAS  Google Scholar 

  24. Shipilovskikh, S.A., Shipilovskikh, D.A., and Rubtsov, A.E., Russ. J. Org. Chem., 2017, vol. 53, p. 137.

    Article  CAS  Google Scholar 

  25. Stewart, W.E. and Siddall, T.H., Chem. Rev., 1970, vol. 70, no. 5, p. 517.

    Article  CAS  Google Scholar 

  26. CrysAlisPro, version 1.171.36.28 (release 01-02-2013 CrysAlis171.NET), Agilent Technologies.

  27. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

  28. Becker, H.G.O., et al., Organikum. Organischchemisches Grundpraktikum, Weinheim: Wiley, 2004, 22nd edn. Translated under the title Organikum, Moscow: Mir, 2008, vol. 2, p. 488.

    Google Scholar 

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Correspondence to A. E. Rubtsov.

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Original Russian Text © A.Yu. Vasileva, V.Yu. Vaganov, S.A. Shipilovskikh, A.E. Rubtsov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 4, pp. 581–586.

For communication XIV, see [1].

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Vasileva, A.Y., Vaganov, V.Y., Shipilovskikh, S.A. et al. Chemistry of Iminofurans: XV. Decyclization of Ethyl 2-[5-Aryl-2-oxofuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylates by the Action of Secondary Amines. Russ J Org Chem 54, 582–587 (2018). https://doi.org/10.1134/S1070428018040115

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  • DOI: https://doi.org/10.1134/S1070428018040115

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