Some reactions and properties of triethylammonium 2-oxo-1-(2-oxoindoline-3-ylidene)-2-phenylethane-1-thiolate

α-Thiocyanate carbonyl compounds occupy a special place in modern organic and heterocyclic chemistry, acting as highly reactive bifunctional synthons. Their unique value lies in the combination of an electrophilic carbonyl center and the rich reactive chemistry of the thiocyanate group (-SCN) separated by an activated α-carbon atom. This architecture determines their role as strategic intermediates for the construction of a wide range of sulfur-containing heterocyclic systems. Organic compounds that contain a thiocyanate group have been used as precursors for agrochemicals, dyes, and medicines. This fragment is an important functional group in several anticancer pharmaceuticals.

Previously, the reaction of thiocyanatoacetophenone (phenacyl thiocyanate) with isatin in the presence of triethylamine was described in the literature. We investigated the properties of the product, triethylammonium 2-oxo-1-(2-oxoindoline-3-ylidene)-2-phenylethane-1-thiolate. The resulting thiolate was introduced in the alkylation reaction, which proceeds regioselectively at sulfur atom. The structure of the products has been characterized by spectral methods, including Fourier IR spectrophotometry and 1H and 13C NMR spectroscopy. The agrochemical potential was also investigated. A study of the herbicide safening effect against herbicide 2,4-D on sunflower seedlings has shown that the compounds obtained exhibit sufficiently high activity and can be used as plant protection agents.