Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione

Xiaoli Ren, Yifei Ling, Jun Luo
2014 Youji huaxue  
A novel compound bicyclo[3.3.1]nonane-2,6,9-trione was synthesized from cyclohexane-1,3-dione through three routes and some reaction mechanisms were proposed. The first route afforded bicyclo[3.3.1]nonane-2,6,9-trione in a total yield of 43% via Michael addition with cyclohexane-1,3-dione and acrolein, intermolecular Aldol condensation and oxidation. The second route gave target product in 20% yield via a one-pot process including formation of enamine with morpholine and cyclization with
more » ... ization with acrylic ethyl ester. The third route also used cyclohexane-1,3-dione and acrylic ethyl ester as start materials and resulted bicyclo[3.3.1]nonane-2,6,9-trione with a high total yield of 83% via Michael addition and intermolecular C-acylation. This process has the advantages of simple operation, mild reaction conditions, high yield and environmental friendship.
doi:10.6023/cjoc201309009 fatcat:lcawqf6o7bhbhh7gtisvvcctxm