Synthesis and Properties of Polyfunctional Cyclic β‐Alkoxy‐α,β‐Unsaturated Ketones Based on 4‐Methylene‐1,3‐dioxolanes

Abstract

New CCl 3 ‐ and CF 3 ‐substituted enones, bearing additional hidden hydroxymethyl functions, were prepared by acylation of 4‐methylene 1,3‐dioxolanes. The synthesized enones are interesting building blocks for agrochemical and medicinal chemistry research. The reactivity of synthesized enones with various amines was studied, and enaminones 13 and 14 were obtained under NH 3 interaction; the reaction with aliphatic primary amines afforded enaminones 17 in high yields as equilibrium mixtures of E and Z isomers. The reaction of fluorinated enone 9c with anilines afforded a mixture of products, including non‐aromatic heterocyclic compounds 25 and 26 bearing the CF 3 group as well as furan 27 with CF 3 and amino functions at positions 5 and 3, respectively. The hydrolysis of enone 9c afforded cyclic compound 11 .