SYNTHESIS AND TRANSFORMATION OF TERTIARY HYDROXYMETHYLAMINES CONTAINING gem-DICHLOROCYCLOPROPYL AND CYCLOACETAL FRAGMENTS

Abstract

1,3,5-Triazine derivatives containing one and two cycloacetal and gem-dichlorocyclopropane fragments find application as additives and biologically active substances, alkylamines containing gem-dichlorocyclopropane groups suppress the growth and development of dicotyledonous plants at the level of imported reagents. Many amino alcohols are widely used in the production of detergents, emulsifiers, cosmetic and pharmaceutical products. Based on this the efficient method for the preparation of N-hydroxymethylamines containing gem-dichlorocyclopropane and cycloacetal fragments in the presence of FeCl3·6H2O as a catalyst is proposed. The compounds with a carbamate group have a pronounced biological and pharmacological activity, which determines their effective use for the preparation of drugs for the medical and agricultural industries. Therefore, the reaction of aromatic structures containing carbocyclic fragment with phenyl isocyanate and acid chlorides were studied with subsequent of the formation of the corresponding urethane and esters with yield of (30-93%). It was found that the reaction with p-toluenesulfonic acid chloride is much more difficult and the yield of the desired product, benzyl [(2,2-dichlorocyclopropyl)methyl]aminomethyl-4-methylbenzenesulfonate, does not exceed 30%. The structures of the obtained compounds were investigated by 1H and 13C NMR spectroscopy and found that the gem-dichlorocyclopropane and cycloacetal groups are preserved during the conversions. Isomeric 2- and 4-chloromethyl-1,3-dioxolanes under the conditions studied have the same activity, but substantially inferior to 2-chloromethyl-gem-dichlorocyclopropane. The presented results suggest the wide possibilities of using tertiary hydroxymethylamines containing cycloacetal and cyclopropane fragments in the synthesis of complex carbo- and heterocyclic structures. Moreover, carbo- and heterocyclic compounds with alkylamino groups have proven biological activity.Forcitation:Raskildina G.Z., Valiev V.F., Mirakyan S.M., Chanishev R.R., Zlotskii S.S. Synthesis and transformation of tertiary hydroxymethylamines containing gem-dichlorocyclopropyl and cycloacetal fragments. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2017. V. 60. N 10. P. 16-21