Skip to main content
SpringerLink
Log in

The Mannich reaction in the synthesis of N,S-containing heterocycles. 7. Effective one-pot synthesis of derivatives of spiro[3,5,7,11-tetraazatricyclo-[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

5,11-Disubstituted derivatives of 1′-isopropyl-8-thioxospiro[3,5,7,11-tetrazatricyclo[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]-1,9-dicar bonitrile was obtained by the interaction of 10-amino-9-aza-3-azonia-7,11-dicyano-3-isopropylspiro[5,5]undeca-7,10-diene-8-thiolate with 2 equiv. of a primary amine and excess of formaldehyde. An anomalous reaction product was obtained with o-toluidine — 7,9-dicyano-1′-isopropyl-3-(2-methylphenyl)-1,2,3,4-tetrahydrospiro[pyrido[1,2-a][1,3,5]triazine-8,4′-piper idinium]-6-thiolate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Izv. Acad. Nauk, Ser. Khim., 1418 (2007).

  2. V. P. Litvinov, V. K. Promonenkov, Yu. A. Sharanin, and A. M. Shestopalov, in: Results of Science and Technology. Organic Chemistry. Current Research Directions and Applications of Chemical Preparations in Plant Protection. Chemistry of Azines. [In Russian]. VINITI, Moscow, 1989, Vol. 17, Ch. 2, p.73.

    Google Scholar 

  3. V. P. Litvinov, S. G. Krivokolysko, and V. D. Dyachenko, Khim. Geterotsikl. Soedin., 579 (1999). [Chem. Heterocycl. Comp., 35, 509 (1999)].

    Google Scholar 

  4. V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2123 (1998).

  5. V. P. Litvinov, V. V. Dotsenko, and S. G. Krivokolysko, Izv. Akad. Nauk, Ser. Khim., 847 (2005).

  6. V. P. Litvinov, V. V. Dotsenko, and S. G. Krivokolysko, Chemistry of Thienopyridines and Related Systems [in Russian], Nauka, Moscow, 2006.

    Google Scholar 

  7. E. A. Bakhite, Phosphorus, Sulfur, and Silicon. 178, 929 (2003).

    Article  CAS  Google Scholar 

  8. I. M. Orudzheva, T. E. Efendiev, and S. M. Aliev, Zh. Org. Khim., 17, 410 (1981).

    CAS  Google Scholar 

  9. Z. Wang, Haoxin Shi, Haijian Shi, Synth. Commun., 31, 2841 (2001).

    Article  CAS  Google Scholar 

  10. Z. Wang, T. You, Haijian Shi, Haoxin Shi, Molecules, 1, 89 (1996). Avail URLs: http://www.mdpi.net/molecules/list96.htm; http://www.springerlink.com.

    Article  CAS  Google Scholar 

  11. Z. Wang, T. You, Haijian Shi, Haoxin Shi, Gaodeng Xuexiao Huaxue Xuebao, 18, 550 (1997); Chem. Abstr., 127, 95265 (1997).

    Google Scholar 

  12. Hao-Xin Shi, Hai-Jian Shi, Z. Wang, Youji Huaxue, 20, 344 (2000); Chem. Abstr., 133, 120280 (2000).

    CAS  Google Scholar 

  13. Z. A. Hozein, A. A. O. Sarhan, H. A. H. El-Sherief, and A. H. Mahmoud, Z. Naturforsch., Teil B, 52, 1401 (1997); Chem. Abstr., 128, 88906 (1998).

    Google Scholar 

  14. Haijian Shi, Haoxin Shi, Z. Wang, J. Heterocycl. Chem., 38, 929 (2001).

    Article  CAS  Google Scholar 

  15. Haijian Shi, Z. Wang, Haoxin Shi, Chimia, 51, 529 (1997).

    Google Scholar 

  16. Haijian Shi, Z. Wang, Haoxin Shi, Synth. Commun., 29, 2027 (1999).

    Article  CAS  Google Scholar 

  17. S. Yadav Lal Dhar, A. Vaish, and S. Sharma, J. Agr. Food Chem., 42, 811 (1994).

    Article  Google Scholar 

  18. K. A. Frolov, V. V. Dotsenko, S. G. Krivokolysko, and V. I. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2158 (2005).

  19. Z. A. Hozein, J. Chem. Res. (S); No. 3, 99 (2000).

  20. A. O. Sarhan, S. H. Abdel-Hafez, H. El-Sherief, and T. Aboel-Fadl, Synth. Commun., 36, 987 (2006).

    Article  CAS  Google Scholar 

  21. V. V. Dotsenko, S. G. Krivokolysko, A. N. Chernega and V. P. Litvinov, Dokl. Akad. Nauk, 389, 763 (2003).

    Google Scholar 

  22. V. V. Dotsenko, Dis. Kand. Chim. Nauk, Moscow (2004).

  23. V. V. Dotsenko, S. G. Krivokolysko, and V. I. Litvinov, Khim. Geterotsikl. Soedin., 1695 (2005).[Chem. Heterocycl. Comp., 41, 1394 (2005)].

    Google Scholar 

  24. V. V. Dotsenko, S. G. Krivokolysko, and V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2605 (2005).

  25. A. A. Shestopalov, Dis. Cand. Chem. Sci., Moscow (2004).

Download references

Author information

Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal East-Ukrainian National University, Lugansk, 91034, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Krivokolysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. P. Litvinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. G. Krivokolysko.

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, 1709–1713, November, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dotsenko, V.V., Krivokolysko, S.G. & Litvinov, V.P. The Mannich reaction in the synthesis of N,S-containing heterocycles. 7. Effective one-pot synthesis of derivatives of spiro[3,5,7,11-tetraazatricyclo-[7.3.1.02,7]tridec-2-ene-13,4′-piperidine]. Chem Heterocycl Comp 43, 1455–1459 (2007). https://doi.org/10.1007/s10593-007-0224-5

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-007-0224-5

Keywords

Search

Navigation