α-Nitrocycloalkanones as a new source for the one-pot synthesis of functionalized 1,4-diketones, γ-oxoaldehydes, γ-ketoesters, and methyl ω-oxoalkanoates

Abstract

Methyl ω-oxoalkanoates were obtained via ring cleavage of α-nitrocycloakanones by refluxing these compounds in a methanolic solution of KOH, then treating the obtained mixture, at 0°C, with an aqueous solution of KMnO4/MgSO4. 1,4-Diketones, γ-oxoaldehydes, and γ-ketoesters were also prepared by conjugated addition of α-nitrocycloakanones to the appropriate conjugated enones, in MeOH/Ph3P, then by, in situ, ring cleavage-Nef reaction following the above conditions.