ARYLSULPHONATES OF SPIROPYRAZOLINES AND O-TOSILATE- β-(BENZIMIDAZOL-1-YL)PROPIOAMIDOXYME AS THE PRODUCTS OF β-AMINOPROPIOAMIDOXIMES TOSYLATION

АРИЛСУЛЬФОНАТЫ СПИРОПИРАЗОЛИНОВ И О-ТОЗИЛАТ-β-(БЕНЗИМИДАЗОЛ-1-ИЛ)ПРОПИОАМИДОКСИМА

Abstract

Abstract: Introduction. Pyrazolinium structures have practically valuable biological properties. Their methods of synthesis mainly consist in the reactions of cyclization of steroid compounds containing an enone fragment with a variety of hydrazines. We have previously obtained new spiropyrazolinium compounds by hydrolysis of 3-(β-heteroamino)ethyl-5-aryl-1,2,4-oxadiazoles and by arylsulfochlorination of β-aminopropioamidoximes. The aim of the work is to reveal the dependence of the structure of the final β-aminopropioamidoximes tosylation products from the structure of the starting amidoxime and strength of base. Methodology. The tosylation of β-aminopropioamidoximes was carried out in chloroform using diisopropylethylamine as a base. The synthesis was carried out at room temperature for 15–20 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the precipitate was filtered off, followed by evaporation of the filtrate and additional precipitation of the product; the combined precipitates were recrystallized from isopropanol. Results and discussion. The products of tosylation of β-aminopropioamidoximes were obtained in 45‒65% yields and identified using physicochemical and spectral [IR, NMR (¹H and ¹³C)] characteristics, tosylation of β-aminopropioamidoximes (β-amino group: piperidin-1-yl, morpholine -1-yl, thiomorpholin-1-yl, 4-phenyl-piperazin-1-yl) proceeds with the formation of spirocyclic compounds ‒ arylsulfonates of 2-amino-1,5-diazaspiro [4.5]-dec-1-ene-5-ammonium; tosylation of β-(benzimidazol-1-yl)propioamidoxime gives the product on the oxygen atom of the amidoxime group.