Consecutive Michael-Claisen Process for Cyclohexane-1,3-dione Derivative (CDD) Synthesis from Unsubstituted and Substituted Acetone

A long-existing problem of cyclohexane-1,3-dione derivatives (CDD) synthesis from unreactive acetone through consecutive Michael–Claisen process was solved under this study. The practical applicability of this process was tested for a novel compound ethyl 3-(2,4-dioxocyclohexyl)propanoate for up to 20-gram scale. Furthermore, the scope of different acetone derivatives was investigated and resulted with similar consecutive Michael–Claisen process for CDD synthesis. The reaction exhibited remarkable regioselectivity in Michael addition followed by Claisen cyclization. In this process high substrate selectivity was observed for CDD ­synthesis following consecutive double-Michael–Claisen and ­Michael–Claisen cyclization.