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Synthesis of 4-alkyl-6-amino-3,5-dicyano-2(1H)-pyridinethiones

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Condensation of aliphatic aldehydes with cyanothioacetamide has given 4-alkyl-6-amino-3,5-dicyano-2(1H)-pyridinethiones, which have also been synthesized by recyclization of 4-alkyl-2,6-diamino-4H-thiopyrans. Substituted 2-alkylthiopyridines and thieno[2,3-b]pyridines have been prepared from the pyridinethiones. 2,6-Diamino-4-isopropyl-3,5-dicyano-4H-thiopyran and 6-amino-4-isobutyl-2-methylthio-3,5-dicyanopyridine have been studied by x-ray crystallography.

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References

  1. N. G. Frolova, V. K. Zav'yalova, and V. P. Litvinov, Izv. Russ. Akad. Nauk., Ser. Khim., No. 4, 938 (1996).

    Google Scholar 

  2. V. G. Kul'nevich, E. A. Kaigorodova, I. S. Arustamova, L. V. Korobchenko, G. V. Vladyko and E. I. Boreko, Khim.-farm. Zh., No. 2, 132 (1990).

    Google Scholar 

  3. V. Hagen, E. Klauschenz, A. Rumler, A. Hagen, S. Heer, R. Nitzner, H. Niedrich, and D. Lohmann, Pharmazie,45, 189 (1990).

    Google Scholar 

  4. V. Hanfeld, S. Leistner, G. Wagner, D. Lohmann, H. Hoppe, and S. Heer, Pharmazie,44, 12 (1989).

    Google Scholar 

  5. A. Rumler, V. Hagen, and A. Hagen, Pharmazie,45, 657 (1990).

    Google Scholar 

  6. W. S. Saari, J. S. Wai, T. E. Fisher, C. M. Thomas, J. M. Hoffman, C. S. Rooney, A. M. Smith, J. H. Jones, D. L. Bamberger, M. E. Goldman, J. A. O'Brien, J. H. Nunberg, J. C., Quintero, W. A. Schleif, E. A. Emini, and P. S. Anderson, J. Med. Chem.,35, 3792 (1992).

    Google Scholar 

  7. J. S. Wai, T. M. Williams, D. L. Bamberger, T. E. Fisher, J. M. Hoffman, R. J. Hudcosky, S. C. MacTough, C. S. Rooney, W. S. Saari, C. M. Thomas, M. E. Goldman, J. A. O'Brien, E. A. Emini, J. H. Hunberg, J. C. Quintero, W. A. Schlief, and P. S. Anderson, J. Med. Chem.,36, 249 (1993).

    Google Scholar 

  8. Yu. A. Sharanin, A. M. Shestopalov, V. N. Nesterov, S. N. Melenchuk, V. K. Promonenkov, V. E. Shklover, Yu. T. Struchkov, and V. P. Litvinov, Zh. Org. Khim.,25, 1323 (1989).

    Google Scholar 

  9. V. D. Dyachenko, V. N. Nesterov, Yu. T. Struchkov, Yu. A. Sharanin, and V. E. Shklover, Zh. Obshch. Khim.,59, 881 (1989).

    Google Scholar 

  10. J. Bellanato, F. Florencio, S. G. Blanco, N. Martin, and C. Seoane, J. Mol. Struct.,19, 162 (1987).

    Google Scholar 

  11. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc., Perkin Trans. II, No. 12, S1 (1987).

    Google Scholar 

  12. A. Bondi, J. Phys. Chem.,70, 3006 (1966).

    Google Scholar 

  13. W. Robinson and G. M. Sheldrick, Crystallographic Computing. Techniques and New Technologies, Oxford University Press (1988), p. 366.

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T. G. Shevchenko State Teaching Institute, Lugansk 348011. A. N. Nesmeyanov Institute of Organoelemental Compounds, Moscow 117813. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1655–1663, December, 1997.

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Dyachenko, V.D., Krivokolysko, S.G., Nesterov, V.N. et al. Synthesis of 4-alkyl-6-amino-3,5-dicyano-2(1H)-pyridinethiones. Chem Heterocycl Compd 33, 1430–1437 (1997). https://doi.org/10.1007/BF02291644

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