Abstract
Cyclohexanone condensation with formaldehyde and methylamine led to the formation of 4ahydroxy-2-methyloctahydrospiro[isoquinoline-4,1'-cyclohexan]-2'-one whose structure was established by means of X-ray diffraction (XRD) analysis. This spiro compound reacted with acetylenecarboxylic acids esters with unexpected conversion of its piperidine ring into a hexahydroazocine cycle. The uncommon expansion reaction of the β-acyl-substituted piperidine ring into a hexahydroazocine cycle is confirmed by the analogous conversion of 4-hydroxy-1-methyl-4-phenylpiperidin-3-yl(phenyl)methanone into azocine derivative at treating with methyl propiolate.
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Original Russian Text © A.V. Malkova, K.B. Polyanskii, A.T. Soldatenkov, S.A. Soldatova, N.L. Merkulova, V.N. Khrustalev, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 2, pp. 236–239.
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Malkova, A.V., Polyanskii, K.B., Soldatenkov, A.T. et al. Uncommon expansion of piperidine ring into hydroazocine ring in reactions of some piperidine β-acyl derivatives with acetylenecarboxylic acids esters. Russ J Org Chem 52, 219–222 (2016). https://doi.org/10.1134/S107042801602010X
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DOI: https://doi.org/10.1134/S107042801602010X