V. Yu., K. Praliyev, A. Nagimova
Mar 25, 2015
Citations
0
Influential Citations
4
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The spirocyclic compounds, 3-cyano-4-methyl-8-(2-ethoxyethyl)-1-oxa-8-azaspiro[4,5]deca-3-ene and 3-cyano-4-methyl-8-(2-phenylethyl)-1-oxa-8-azaspiro[4.5]dec-3-ene were unexpectedly obtained from the reaction of 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine and 1-(2-phenylethyl)-4-acetyl-4-hydroxypiperidine with acrylonitrile at room temperature in the presence of an alkali catalyst; further hydrolysis led to the corresponding carboxylic acids. The spirocyclic compounds are thought to form via an aldol condensation which follows cyanoethylation. However, the reaction of 3-butoxypropyl-2-cyanoethylamine with 1-(2-ethoxyethyl)-4-acetyl-4-hydroxypiperidine leads to 1-(2-ethoxyethyl)-4-(1′-hydroxyethyl)-4-hydroxypiperidine.