The synthetic method for 1-(phenyl)alkyl-3-acyl-1,2,8-triazaspiro[4.5]decanes

Authors

  • V. O. Kovtunenko Taras Shevchenko National University of Kyiv, Ukraine
  • L. M. Potikha Taras Shevchenko National University of Kyiv, Ukraine
  • T. S. Bulda State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Ukraine
  • R. I. Zubatyuk State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Ukraine
  • O. V. Shishkin State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.16.874

Keywords:

arylhydrazone, reductive alkylation, 1, 4-dihydropyridine, 5-dihydro-4H-pyrazol-4-on, 2, 8-triaza- spiro[4.5]decane

Abstract

Piperidines spiro-fused to other heterocycles and being structural elements of pharmacologically active molecules can be considered as “preferred fragments” of metabotropic receptor ligands. The method for obtaining 1,2,8-triazaspiro [4.5]decane comprising spiroannelation of 1,4-dihydropyridine and pyrazolone cycles. When heating of 1-(phenyl)alkyl-4-[2-[2-arylhyqrazono]-1,3-dioxobutyl]pyridinium halide in pyridine or by reacting of 1-(phenyl)alkyl-4-[2-[2-arylhyqrazono]-1,3-dioxobutyl]pyridinium halides and 1-(phenyl)alkyl-4-{1,3-dioxo-3-phenyl-2-[2-(4-methylphenyl)hydrazono]propyl}pyridinium halides with diisopropylethylamine at 25°C the intramolecular reductive alkylation of the electrophilic pyridinium cation occurs forming 1-(phenyl)alkyl-3-acyl-1,2,8-triazaspiro[4.5]decanes, which are solid coloured substances. The spectral properties of the cyclization products have been studied; formation of the spiro-fused system and the presence of the 1,4-dihydropyridine fragment have been determined. Confi rmation of their structure has been obtained by carrying out the X-ray diffraction of 3-acetyl-8-benzyl-1-phenyl-1,2,8-triazaspiro[4.5]deca-2,6,9-trien-4-one crystal, which, in its turn, has clearly confi rmed orthogonality of the spiro-fused planes. The dihydropyridine ring in the molecule is not fl at and is located in the half-chair conformation with deviation of carbon spiro atom from the plane of the rest atoms of the cycle. This is due to formation of the intramolecular C-H...π hydrogen bond.

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References

  1. Krafft A. A., Kurt A. A., Thomas A. W., Zimmerli D. Synthesis, 2005, Vol. 19, pp.3245-3252.
  2. Patchett A. A., Nargund R. P., Tata J. R., Chen M. H., Barakat K. J., Johnston D. B., Cheng K., Chan W. W., Butler B., Hickey G. Proceedings of the National Academy of Sciences of the United States of America, 1995, Vol. 92, No.15, pp.7001-7005.
  3. Kisel V. M., Kostyrko E. O., Kovtunenko V. A. Chemistry of Heterocyclic Compounds, 2002, Vol. 38, No.8, pp.940-946.
  4. Bondensgaard K., Ankersen M., Thogersen H. L., Hansen B. S., Wulff B. S., Bywater R.P. Journal of Medicinal Chemistry, 2004, Vol. 47, No.4, pp.888-899.
  5. Patchett A. A. Journal of Medicinal Chemistry, 2002, Vol. 45, No.26, pp.5609-5616.
  6. Tsukamoto S., Nagaoka H., Igarashi S., Wanibuchi F., Hidaka K., Tamura T. Chemical and Pharmaceutical Bulletin, 1995, Vol. 43, No.9, pp.1523-1529.
  7. Smith P. W., Anthony A. W. J., Bell R., Beresford I. J. M., Gore P. M., McElroy A. B., Pritchard J. M., Saez V., Taylor N. R. Journal of Medicinal Chemistry, 1995, Vol. 38, No.19, pp.3772-3779.
  8. Ahlbrecht H., Krohnke F. Liebigs Annalen der Chemie, 1967, Vol. 704, pp.133-139.
  9. Sainsbury M., Uttley N. L. Journal of Chemical Society, Perkin Transactions I, 1977, pp.2109-2115.
  10. Naito N., Miyata O., Ninomiya I. Journal of Chemical Society, Chemical Communications, 1979, pp.517-518.
  11. Weller D. D., Weller D. L. Tetrahedron Letters, 1982, Vol. 23, No.50, pp.5239-5242.
  12. Naito N., Ninomiya I. Heterocycles, 1981, Vol. 15, No.2, pp.735-738.
  13. Kucherenko T. T., Gutsul R. M., Kysel V. M., Kovtunenko V. O. Tetrahedron, 2004, Vol. 60, No.1, pp.211-217.
  14. Kisel V. M., Kovtunenko V. A., Potikha L. M., Turov A. V., Babichev F. S. Ukrainsky khimichesky zhurnal – Ukrainian chemistry journal, 1993, Vol. 59, No.10, pp.1070-1071.
  15. Kovtunenko V. A., Potikha L. M., Mishchuk A. A., Turov A. V. Chemistry of Heterocyclic Compounds, 2008, Vol. 44, No.8, pp.1019-1021.
  16. Kovtunenko V. A., Potikha L. M., Bulda T. S., Zubatyuk R. I., Shishkin O. V. Zhurnal organichnoi ta farmatsevtichnoi khimii – Journal of organic and pharmaceutical chemistry, 2014, Vol. 12, No.2(46), pp.4-14.
  17. Freeman J. P., Hoare M. J. The Journal of Organic Chemistry, 1971, Vol. 36, No.1, pp.19-23.
  18. Baldwin J. E., Lever O. W. Jr., Tzodikov N. R. The Journal of Organic Chemistry, 1976, Vol. 41, No.17, pp.2874-2877.
  19. Winkler F. K., Dunitz J. D. Journal of Molecular Biology, 1971, Vol. 59, No.1, pp.169-182.
  20. Sheldrick G. M. Acta Crystallographica Section A, 2008, Vol. 64, No.1, pp.112-122.

Published

2016-03-04

How to Cite

(1)
Kovtunenko, V. O.; Potikha, L. M.; Bulda, T. S.; Zubatyuk, R. I.; Shishkin, O. V. The Synthetic Method for 1-(phenyl)alkyl-3-Acyl-1,2,8-triazaspiro[4.5]decanes. J. Org. Pharm. Chem. 2016, 14, 61-66.

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Original Researches