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Synthesis of substituted 2-amino-3-cyano-7,9-dimethyl-4H-pyrano[2",3":4,5]thieno[2,3-b]pyridines

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Abstract

4,6-Dimethyl-2H-thieno[2,3-b]pyridin-3-one reacts with 2-aryl-1,1-dicyanoethylenes or an aromatic aldehyde/ketone (cyclohexanone and piperidone derivatives) and malononitrile to give substituted 2-amino-3-cyano-7,9-dimethyl-4H-pyrano[2",3":4,5]thieno[2,3-b]pyridines.

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References

  1. F. S. Babichev, Yu. A. Sharanin, V. P. Litvinov, V. K. Promonenkov, and Yu. M. Volovenko, Vnutrimolekulyarnoe vzaimodeistvie nitril´noi i C-H-, O-H-i S-H-grupp [Intramolecular Interactions of a Nitrile Group with C-H, O-H, and S-H Groups], Naukova Dumka, Kiev, 1985, 199 pp. (in Russian).

    Google Scholar 

  2. Yu. A. Sharanin, M. P. Goncharenko, and V. P. Litvinov, Usp. Khim., 1998, 67, 442 [Russ. Chem. Rev., 1998, 67 (Engl. Transl.)].

    Google Scholar 

  3. A. M. Shestopalov, Yu. A. Sharanin, M. R. Khikuba, V. N. Nesterov, V. E. Shklover, Yu. T. Struchkov, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 1991, 205 [Chem. Heterocycl. Compd., 1991 (Engl. Transl.)].

  4. A. V. Samet, A. M. Shestopalov, M. I. Struchkova, V. N. Nesterov, Yu. T. Struchkov, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 1996, 2050 [Russ. Chem. Bull., 1996, 45, 1945 (Engl. Transl.)].

  5. V. D. Dyachenko, S. G. Krivokolysko, and V. P. Litvinov, Zh. Org. Khim., 1998, 34, 750 [Russ. J. Org. Chem., 1998, 34, 707 (Engl. Transl.)].

    Google Scholar 

  6. J. L. Mareo, N. Martin, A. Martmez-Grau, C. Seoane, A. Albert, and P. H. Cano, Tetrahedron, 1994, 50, 3509.

    Google Scholar 

  7. A. M. Shestopalov, Z. I. Nijazimbetova, D. H. Evans, and M. E. Nijazimbetov, Heterocycles, 1999, 51, 1101.

    Google Scholar 

  8. A. M. Shestopalov, Y. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya, Z. I. Nijazimbetova, and D. H. Evans, Org. Lett., 2002, 4, 423.

    Google Scholar 

  9. V. S. Velezheva, D. E. Gedz´, D. V. Gusev, A. S. Peregudov, B. V. Lekshin, and Z. S. Klemenkova, Abstrs., Pervaya mezhdunarodnaya konferentsiya "Khimiya i biologicheskaya aktivnost´ azotistykh geterotsiklov i alkaloidov" [1st Int. Conf. "Chemistry and Biological Activity of Nitrogeneous Heterocycles and Alkaloids"] (Moscow, October 9-12, 2000), Iridium-Press, Moscow, 2001, 1, 247 (in Russian).

    Google Scholar 

  10. US Pat. 3 097 213; Ref. Zh., Khim. (Abstract Journal, Chemistry), 1965, 12 N 257P (in Russian).

  11. Eur. Pat. 758 647; Chem. Abstrs., 1997, 126, 225216v.

  12. Eur. Pat. 695 547; Chem. Abstrs., 1995, 122, 23835c.

  13. RF Pat. 2 125 573; Chem. Abstrs., 1999, 121, 108765j.

  14. K. C. Joslhi, R. Jain, and S. Arora, J. Ind. Chem. Soc., 1988, 65, 277.

    Google Scholar 

  15. C. N. O'Callaghan, T. B. N. McMurry, and J. E. O'Brien, J. Chem. Soc., Perkin Trans. 1, 1995, 417.

  16. A. M. Shestopalov, O. A. Naumov, and V. N. Nesterov, Izv. Akad. Nauk, Ser. Khim., 2003, 169 [Russ. Chem. Bull., Int. Ed., 2003, 52, 179].

    Google Scholar 

  17. A. M. Shestopalov and O. A. Naumov, Izv. Akad. Nauk, Ser. Khim., 2003, 911 [Russ. Chem. Bull., Int. Ed., 2003, 52, 961].

  18. O. A. Naumov and A. M. Shestopalov, Abstrs., 2-ya Molodezhnaya nauchnaya shkola po organicheskoi khimii [2nd Junior Scientific School on Organic Chemistry] (Ekaterinburg, May 2-6, 2000), Ekaterinburg, 2000, 134 (in Russian).

  19. O. A. Naumov and A. M. Shestopalov, Abstrs., 3-i Vserossiiskii simpozium "Strategiya i taktika organicheskogo sinteza" [3rd All-Russia Symp. "Strategy and Tactics of Organic Synthesis"] (Yaroslavl´, March 3-7, 2001), Yaroslavl´, 2001, 80 (in Russian).

  20. Yu. A. Sharanin, V. K. Promonenkov, and L. G. Sharanina, Zh. Org. Khim., 1982, 18, 625 [J. Org. Chem. USSR, 1982, 18, 544 (Engl. Transl.)].

    Google Scholar 

  21. Yu. A. Sharanin, L. N. Shcherbina, L. G. Sharanina, and V. V. Puzanova, Zh. Org. Khim., 1983, 19, 164 [J. Org. Chem. USSR, 1983, 19, 150 (Engl. Transl.)].

    Google Scholar 

  22. K. Gewald, M. Hentschel, and U. Illgen, J. Prakt. Chem., 1974, 316, 1030.

    Google Scholar 

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Shestopalov, A.M., Naumov, O.A. Synthesis of substituted 2-amino-3-cyano-7,9-dimethyl-4H-pyrano[2",3":4,5]thieno[2,3-b]pyridines. Russian Chemical Bulletin 52, 1380–1385 (2003). https://doi.org/10.1023/A:1024835412937

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