Метод синтезу 1-(феніл)алкіл-3-ацил-1,2,8-триазаспіро[4.5]деканів

• Date: 2016
• Main Authors: Kovtunenko, V. O., Potikha, L. M., Bulda, T. S., Zubatyuk, R. I., Shishkin, O. V.
• Format: Article
• Language: Russian
• Published: National University of Pharmacy 2016
• Subjects: арилгідразон; відновне алкілування; 1; 4-дигідропіридин; 5-дигідро-4Н-піразол-4-он; 2; 8-триазаспіро[4.5]декан; УДК 547.833
• Online Access: https://ophcj.nuph.edu.ua/article/view/ophcj.16.874
• Journal Title: Journal of Organic and Pharmaceutical Chemistry

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.