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The Mannich reaction in the synthesis of N,S-containing heterocycles 10. Recyclization of stable cyclic michael adducts, N-methylmorpholinium 6-R-6-hydroxy-1,4,5,6-tetrahydropyridine-2-thiolates, to pyrimido[4,3-b][1,3,5]thiadiazines under conditions of aminomethylation reaction

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Abstract

5-Substituted N-methylmorpholinium 4-aryl-6-R-3-cyano-6-hydroxy-1,4,5,6-tetrahydro-pyridine-2-thiolates upon the action of primary amines and HCHO in ethanol undergo recyclization to 3,7-disubstituted 8-aryl-3,4,7,8-tetrahydro-2H,6H-pyrimido[4,3-b][1,3,5]thiadiazine-9-carbonitriles in low yields (5–28%). The latter were also obtained by alternative method, viz., by sequential condensation of cyanothioacetamide with aromatic aldehydes, primary amines, and HCHO.

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References

  1. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2009, 1479 [Russ. Chem. Bull., Int. Ed., 2009, 58, 1524].

    Google Scholar 

  2. I. M. Orudzheva, T. E. Efendiev, S. M. Aliev, Zh. Org. Khim., 1981, 17, 410 [Russ. J. Org. Chem. (Engl. Transl.), 1981, 17].

    CAS  Google Scholar 

  3. V. V. Dotsenko, S. G. Krivokolysko, whereas. N. Chernega, V. P. Litvinov, Dokl. Akad. Nauk, 2003, 389, 763 [Dokl. Chem. (Engl. Transl.), 2003, 389, 92]; (b) V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Monatsh. Chem., 2008, 139, 271.

    Google Scholar 

  4. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Khim. Geterotsikl. Soedin., 2007, 621 [Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 517].

    Google Scholar 

  5. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov. Khim. Geterotsikl. Soedin., 2005, 1695 [Chem. Heterocycl. Compd. (Engl. Transl.), 2005, 41, 1428]

    Google Scholar 

  6. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Monatsh. Chem., 2007, 138, 489

    Article  CAS  Google Scholar 

  7. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2007, 2397 [Russ. Chem. Bull., Int. Ed., 2007, 56, 2482].

    Google Scholar 

  8. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2005, 2605 [Russ. Chem. Bull., Int. Ed., 2005, 54, 2692]

    Google Scholar 

  9. V. V. Dotsenko, S. G. Krivokolysko, A. N. Chernega, V. P. Litvinov, Monatsh. Chem., 2007, 138, 35

    Article  CAS  Google Scholar 

  10. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2007, 1014 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1053].

    Google Scholar 

  11. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Khim. Geterotsikl. Soedin., 2007, 1709 [Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 1455]

    Google Scholar 

  12. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, E. B. Rusanov, Dokl. Akad. Nauk, 2007, 413, 345 [Dokl. Chem. (Engl. Transl.) 2007, 413, 68].

    Google Scholar 

  13. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Monatsh. Chem., 2008, 139, 657.

    Article  CAS  Google Scholar 

  14. S. G. Krivokolysko, Dr. Sci. Thesis, MSU, Moscow, 2001 (in Russian).

  15. V. V. Dotsenko, K. A. Frolov, S. G. Krivokolysko, A. N. Chernega, V. P. Litvinov, Monatsh. Chem., 2006, 137, 1089.

    Article  CAS  Google Scholar 

  16. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2007, 1420 [Russ. Chem. Bull., Int. Ed., 2007, 56, 1474].

    Google Scholar 

  17. A. A. Krauze, E. E. Liepin’sh, Yu. E. Pelcher, Z. A. Kalme, G. Ya. Dubur, Khim. Geterotsikl. Soedin., 1987, 75 [Chem. Heterocycl. Compd. (Engl. Transl.), 1987, 61].

  18. S. G. Krivokolysko, V. D. Dyachenko, A. N. Chernega, V. P. Litvinov, Khim. Geterotsikl. Soedin., 2001, 790 [Chem. Heterocycl. Compd. (Engl. Transl.), 2001, 37, 727].

    Google Scholar 

  19. S. G. Krivokolysko, V. D. Dyachenko, V. N. Nesterov, V. P. Litvinov, Khim. Geterotsikl. Soedin., 2001, 929 [Chem. Heterocycl. Compd. (Engl. Transl.), 2001, 37, 855].

    Google Scholar 

  20. S. G. Krivokolysko, V. D. Dyachenko, V. P. Litvinov, Khim. Geterotsikl. Soedin., 1999, 1370 [Chem. Heterocycl. Compd. (Engl. Transl.), 1999, 35, 1190].

    Google Scholar 

  21. J. S. A. Brunskill, A. De, D. F. Ewing, J. Chem. Soc., Perkin Trans. 1, 1978, 629.

  22. J. Graymore, J. Chem. Soc., 1932, 1353.

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Authors and Affiliations

  1. ChemEx Laboratory, V. Dal’ East-Ukrainian National University, 20a Molodezhnyi kv., 91034, Lugansk, Ukraine

    V. V. Dotsenko, K. A. Frolov & S. G. Krivokolysko

  2. State Enterprise Luganskstandardmetrology, 50 ul. Timiryazeva, 91021, Lugansk, Ukraine

    V. V. Dotsenko

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

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
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  2. K. A. Frolov
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  3. S. G. Krivokolysko
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  4. V. P. Litvinov
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Corresponding author

Correspondence to V. V. Dotsenko.

Additional information

For Part 9, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1436–1440, July, 2009.

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Dotsenko, V.V., Frolov, K.A., Krivokolysko, S.G. et al. The Mannich reaction in the synthesis of N,S-containing heterocycles 10. Recyclization of stable cyclic michael adducts, N-methylmorpholinium 6-R-6-hydroxy-1,4,5,6-tetrahydropyridine-2-thiolates, to pyrimido[4,3-b][1,3,5]thiadiazines under conditions of aminomethylation reaction. Russ Chem Bull 58, 1479–1483 (2009). https://doi.org/10.1007/s11172-009-0199-8

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  • DOI: https://doi.org/10.1007/s11172-009-0199-8

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