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The synthesis of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives

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Abstract

A method for the preparation of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives has been developed. Alkylation of (2,2-dicyano-1-organylaminovinyl)thiolates with methyl 2-(chloromethyl)benzoate or N-substituted 2-(chloromethyl)benzamides with the subsequent treatment of the alkylation products with potassium tert-butoxide gave 3-cyano-2-(organylamino)thieno[3,2-c]isoquinolin-5(4H)-ones. In the case of utilization of (chloromethyl)benzonitrile in this synthesis, 5-amino-3-cyano-2-organylaminothieno[3,2-c]iso-quinolines were obtained.

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References

  1. M. Cushman, M. Jayaraman, J. A. Vroman, A. K. Fukunaga, B. M. Fox, G. Kohlhagen, D. Strumbergt, Y. Pommier, J. Med. Chem., 2000, 43, 3688.

    Article  CAS  PubMed  Google Scholar 

  2. D. Strumberg, Y. Pommier, K. Paull, M. Jayaraman, P. Nagafuji, M. Cushman, J. Med. Chem., 1999, 42, 446.

    Article  CAS  PubMed  Google Scholar 

  3. Pat. WO 00/21537; Chem. Abstr., 2000, 132, 293675t.

  4. C. Szabo, V. L. Dawson, Trends Pharmacol. Sci., 1998, 19, 287.

    Article  CAS  PubMed  Google Scholar 

  5. US Pat. 7,393,955, 2008; Chem. Abstr., 2008, 149, 128753.

  6. V. E. Kalugin, A. M. Shestopalov, Tetrahedron Lett., 2011, 52, 1557.

    Article  CAS  Google Scholar 

  7. V. E. Kalugin, A. M. Shestopalov, Russ. Chem. Bull., 2014, 63, 2478.

    Article  CAS  Google Scholar 

  8. V. E. Kalugin, A. M. Shestopalov, Russ. Chem. Bull., 2015, 64, 878.

    Article  CAS  Google Scholar 

  9. V. E. Kalugin, A. M. Shestopalov, Russ. Chem. Bull., 2014, 63, 426.

    Article  CAS  Google Scholar 

  10. V. E. Kalugin, A. M. Shestopalov, Russ. Chem. Bull., 2017, 66, 2478.

    Article  CAS  Google Scholar 

  11. V. E. Kalugin, A. M. Shestopalov, Russ. Chem. Bull., 2018, 67, 902.

    Article  CAS  Google Scholar 

  12. V. E. Kalugin, A. M. Shestopalov, Russ. Chem. Bull., 2018, 67, 1492.

    Article  CAS  Google Scholar 

  13. Pat. WO 2006069182; Chem. Abstr., 2006, 145, 83249.

  14. K. Gewald, U. Hain, M. Shmidt, J. Pract. Chem., 1986, 323, 459–464.

    Google Scholar 

  15. G. Sommen, A. Camel, G. Kirsch, Tetrahedron, 2003, 59, 1557.

    Article  CAS  Google Scholar 

  16. R. M. Mohareb, S. El-Kousy, A. M. El-Torgoman, Collect, 1992, 57, 1747.

    CAS  Google Scholar 

  17. V. A. Kovtunenko, A. K. Tyltin, T. T. Dobrenko, F. S. Babichev, Ukr. Khim. Zh., 1983, 49, 1099.

    CAS  Google Scholar 

  18. T. Mukayama, H. Tanaka, Bull. Chem. Soc. Jpn, 1956, 29, 908.

    Article  Google Scholar 

  19. I. G. Hinton, F. G. Mann, J. Chem. Soc., 1959, 599.

    Google Scholar 

Download references

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. E. Kalugin & A. M. Shestopalov

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  1. V. E. Kalugin
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  2. A. M. Shestopalov
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Correspondence to V. E. Kalugin.

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Kalugin, V.E., Shestopalov, A.M. The synthesis of 3-cyano-2-(organylamino)thieno[3,2-c]isoquinoline derivatives. Russ Chem Bull 68, 588–596 (2019). https://doi.org/10.1007/s11172-019-2459-6

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  • DOI: https://doi.org/10.1007/s11172-019-2459-6

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