Regio- and stereochemical features of the reactions of 1,2,5-trimethylpiperidin-4-one with chalcone |
| |
| Authors: | S. Z. Vatsadze M. L. Kostochka V. P. Lezina V. G. Vinokurov N. V. Zyk |
| |
| Affiliation: | (1) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899 Moscow, Russian Federation;(2) Research Institute of Pharmacology, Russian Academy of Medical Sciences, 8 ul. Baltiiskaya, 125315 Moscow, Russian Federation |
| |
| Abstract: | The reactions of N-substituted piperidin-4-ones with benzylideneacetophenone, resulting in the synthesis of a number of heterocyclic 1,5-dicarbonyl compounds, were studied. 1,2,5-Trimethylpiperidin-4-one enters into cascade-type chalcone addition accompanied by intramolecular aldol condensation giving rise to the 3-azabicyclo[3.3.1]nonane system. The conformations of the 1,5-dicarbonyl compounds and azabicyclononanes synthesized were determined; the regio- and stereochemical features of the reactions of 1,2,5-trimethylpiperidin-4-one with chalcone were studied.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2693–2697, December, 2004. |
| |
| Keywords: | Michael reaction N-benzylpiperidin-4-one 8-methyl-2-(3-oxo-1 3-diphenylpropyl)-8-azabicyclo[3.2.1]octan-3-one 1,2,5-trimethyl-3-(3-oxo-1,3-diphenylpropyl)piperidin-4-one 1-methyl-3-(3-oxo-1,3-diphenylpropyl)piperidin-4-one 3-azabicyclo[3.3.1]nonan-9-ones aldol condensation thermodynamic control |
| 本文献已被 SpringerLink 等数据库收录！ |
|
