SYNTHESIS AND CHEMICAL MODIFICATION OF NEW HYDROXYBEZALDEHYDE DERIVATIVES
Keywords:sodium xanthates, thioanhydrides, propargylation, acetylenic and thioacetylenic ethers
Introduction. A high pharmacological ability of aromatic benzaldehydes makes them important intermediates for the synthesis of medicinal preparations, such as anticancer, bactericidal, antifungal, and herbicidal drugs. The purpose of this work is the synthesis of biologically active compounds, based on 4-hydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde and the establishment of the structure of the synthesized compounds. Results and discussion. New carbonodithioates, based on O-aromatic systems have been synthesized by the interaction of 4-hydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde with carbon disulfide in the presence of sodium hydroxide in ethanol at the room temperature. As a result of the reactions, sodium O-(4-formylphenyl)carbodithioate (86 %) and sodium O-(4-formyl-2-methoxyphenyl)carbodithioate (80%) have been isolated. The interaction of sodium xanthates with acid chlorides (4-methoxy-, 4-nitro-, 2,4-dinitrobenzoic) in chloroform has led to the formation of aromatic thioanhydrides of carbonodithioic acids in 55-80 % yields. The reactivity of hydroxybenzaldehydes and their dithiocarboxylic derivatives has been studied in the propargylation reaction. Propargylation of 4-hydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde has been carried out with propargyl bromide in the presence of a 3-fold excess of K2CO3 in acetone at the temperature of 60°C. The propargylation reaction of sodium xanthate has been carried out with propargyl bromide in acetone at the room temperature. Conclusion. As a result of the reactions, carbonodithioates, thioanhydrides, acetylenic and thioacetylenic ethers have been synthesized based, on O-aromatic systems (4-hydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde). The structure of the synthesized compounds has been established on the basis of elemental analysis data, IR spectra, 1Н and 13С NMR spectroscopy.