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

V. O. Kovtunenko, L. M. Potikha, T. S. Bulda, R. I. Zubatyuk, O. V. Shishkin

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.

Keywords


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

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

Abbreviated key title: Ž. org. farm. hìm.

ISSN 2518-1548 (Online), ISSN 2308-8303 (Print)