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New Synthesis of Tetrahydroisoquinolines

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Abstract

The reaction of cyclohexylidenecyanothioacetamide with N,N-dimethylformamide dimethyl acetal was studied. This transformation, depending on the reaction conditions, leads to different results: when the starting reagents are refluxed without a solvent, 3-(methylsulfanyl)-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile is formed, and refluxing in benzene leads to 2-cyano-3-(dimethylamino)prop-2-enethioamide. The structure of these products was studied by XRD analysts.

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REFERENCES

  1. Shi, J. Baran Group Meeting. 2006, vol. 10, p. 1.

  2. Izbrannyye metody sinteza i modifikatsii geterotsiklov. Izokhinoliny. Khimiya i biologicheskaya aktivnost’ (Selected methods for the synthesis and modification of heterocycles. Isoquinolines. Chemistry and biological activity), Kartzev, V.G., Ed., Moscow: ICSPF, Fond, Nauchnoe partnerstvo, 2008, vol. 7.

  3. Ashwell, G.J., Ranjan, R., Whittam, A.J., and Gandolfo, D.S., J. Mater. Chem., 2000, vol. 10, p. 63. https://doi.org/10.1039/a902954k

    Article  CAS  Google Scholar 

  4. Ashwell, G.J., Maxwell, A.A., and Green, A., J. Mater. Chem., 2002, vol. 12, p. 2192. https://doi.org/10.1039/B200565B

    Article  CAS  Google Scholar 

  5. Ashwell, G.J. and Gandolfo, D.S., J. Mater. Chem., 2002, vol. 12, p. 411. https://doi.org/10.1039/B109872C

    Article  CAS  Google Scholar 

  6. Hsin, L.-W., Chang, L.-T., Rothman, R.B., Dersch, C.M., Fishback, J.A., and Matsumoto, R.R., J. Med. Chem., 2010, vol. 53, p. 1392. https://doi.org/10.1021/jm901503e

    Article  CAS  PubMed  Google Scholar 

  7. Kamal, A.M., Radwan, S.M., and Zaki, R.M., Eur. J. Med. Chem., 2011, vol. 46, p. 567. https://doi.org/10.1016/j.ejmech.2010.11.036

    Article  CAS  PubMed  Google Scholar 

  8. Dyachenko, I.V. and Dyachenko, V.D., Russ. J. Org. Chem., 2017, vol. 53, p. 1769. https://doi.org/10.1134/s1070428017120016

    Article  CAS  Google Scholar 

  9. Dyachenko, I.V. and Vovk, M.V., Russ. J. Org. Chem., 2013, vol. 49, p. 787. https://doi.org/10.1134/s107042801305028x

    Article  Google Scholar 

  10. Dyachenko, I.V., Rusanov, E.B., and Vovk, M.V., Russ. J. Org. Chem., 2013, vol. 49, p. 1379. https://doi.org/10.1134/s1070428013090224

    Article  Google Scholar 

  11. Sukach, S.M. and Dyachenko, V.D., Russ. J. Org. Chem., 2015, vol. 51, p. 903. https://doi.org/10.1134/s1070428015060160

    Article  CAS  Google Scholar 

  12. Dyachenko, V.D., Dyachenko, I.V., and Nenajdenko, V.G., Russ. Chem. Rev., 2018, vol. 87, p. 1. https://doi.org/10.1070/rcr4760

    Article  CAS  Google Scholar 

  13. Smit, M., Organicheskaya khimiya Marcha. Reaktsii, mekhanizmy, stroyeniye: uglublennyy kurs dlya universitetov i khimicheskikh vuzov (March Organic Chemistry. Reactions Mechanisms Structure: An Advanced Course for Universities and Chemical Universities), Moscow: Laboratoriya znanii, 2020, vol. 2.

  14. Litvinov, V.P., Yakunin, Ya.Yu., and Dyachenko, V.D., Chem. Heterocycl. Compd., 2001, vol. 37, p. 37. https://doi.org/10.1023/A:1017536700235

    Article  CAS  Google Scholar 

  15. Pushkareva, T.I. and Zenkevich, I.G., Vestn. SPbGU, Ser. 4, 2015, vol. 2, p. 269.

    Google Scholar 

  16. Dyachenko, I.V., Russ. J. Gen. Chem., 2019, vol. 89, p. 896. https://doi.org/10.1134/S1070363219050062

    Article  CAS  Google Scholar 

  17. Bruker, SAINT, Bruker AXS Inc., Madison, WI, 2012.

  18. Battye, T.G.G., Kontogiannis, L., Johnson, O., Powell, H.R., and Leslie, A.G.W., Acta Crystallogr., Sect. D, 2011, vol. 67, p. 271. https://doi.org/10.1107/S0907444910048675

    Article  CAS  Google Scholar 

  19. Sheldrick, G.M. SADABS, Bruker/Siemens Area Detector Absorption Correction Program; Bruker AXS Inc., Madison, WI, 2003.

  20. Evans, P.R., Acta Crystallogr., Sect. D, 2006, vol. 62, p. 72. https://doi.org/10.1107/S0907444905036693

    Article  CAS  Google Scholar 

  21. Sheldrick, G.M., Acta Crystallogr., Sect. C, 2015, vol. 71, p. 3. https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  22. Abdel-Latif, F.F., Pharmazie, 1990, vol. 45, p. 283.

    CAS  Google Scholar 

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Correspondence to V. G. Nenajdenko.

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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 5, pp. 469–475 https://doi.org/10.31857/S0514749222050032.

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Dyachenko, I.V., Dyachenko, V.D., Dorovatovskii, P.V. et al. New Synthesis of Tetrahydroisoquinolines. Russ J Org Chem 58, 657–662 (2022). https://doi.org/10.1134/S1070428022050037

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