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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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.

Issue

Vol. 14 No. 1(53) (2016)

Section

Original Researches

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