Preparation of cyclic acetals and gem-dichlorocyclopropanes based on 1,2-dichloromethylbenzol

Abstract

Using 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane (sol-ketal) and 1,2-dichlomethylbenzene under the conditions of phase transfer catalysis, mono- and diesters containing cycloacetal fragments were synthesized. Also, with the help of dichloride, in the presence of benzene, mono- and diesters of allyl alcohol were obtained. Dichlorocyclopropanation of unsaturated ethers using chloroform, alkali and catamine AB catalyst made it possible to obtain compounds containing gem-dichlorocyclopropane fragments. O-alkylation of the sol-ketal with 1-[(alloxy)methyl]-2-(chloromethyl)benzene (mono-derivative of allyl alcohol) was used to synthesize an ether combining in its structure 1,3-dioxolane and gem-dichlorocyclopropane fragments simultaneously. The obtained substances were analyzed and confirmed by mass spectrometry («Chromatek-Kristall» instrument with Nist research database) and NMR spectroscopy («Bruker instrument»). It was found that among a number of compounds obtained, only 4-{[(2-{[(2,2-dichlorocyclopropyl) methoxy]methyl}-benzyl)oxy] methyl}-2,2-dimethyl-1,3-dioxolane exhibits cytological activity against the cell lines HEK293, SH-SY5Y, MCF-7 and A549.