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Synthesis and Properties of Polyfunctional Cyclic β‐Alkoxy‐α,β‐Unsaturated Ketones Based on 4‐Methylene‐1,3‐dioxolanes
Author(s) -
Gerus Igor I.,
Balabon Olga A.,
Pazenok Sergiy V.,
Lui Norbert,
Kondratov Ivan S.,
Tarasenko Karen V.,
Shaitanova Ele.,
Ivasyshyn Viktor E.,
Kukhar Valery P.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800786
Subject(s) - chemistry , enone , methylene , furan , alkoxy group , reactivity (psychology) , hydroxymethyl , hydrolysis , organic chemistry , medicinal chemistry , medicine , alkyl , alternative medicine , pathology
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 .