## 2 Topical Research Areas Related to Ionic Liquids and the Contribution of Spiroammonium Compounds  
### Synthesis and Structure of the New Biologically Active 2-Aminospiropyrazolylammonium Salts  
In arylsulfochlorination reactions of amidoximes, the formation of a spectrum of products has been noted. Thus, stable aromatic and heteroaromatic O-sulfonyl amidoximes, obtained via the reaction of substituted benzamidoximes and pyridine carboxylic acid amidoximes with aromatic and aliphatic sulfonyl chlorides, have been described. The sulfochlorination of structurally different amidoximes can afford O-sulfonyl amidoximes, ureas, and cyanamides [3; 4; 5; 6]. For the first time, we performed the arylsulfochlorination of \(\beta\)-aminopropioamidoximes with six-membered heterocycles in the \(\beta\)-position (piperidine, morpholine, thiomorpholine, and phenylpiperazine) in the presence of diisopropylthelylamine (DIPEA) in chloroform and found that a series of 2-aminospiropyrazolinium salts (with cation 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium and the anions arylsulfonates, hexafluorophosphate, chloride) formed. Among the arylsulfochlorination products of \(\beta\)-aminopropioamidoximes, their structural isomers O-sulfonyl-\(\beta\)-aminopropioamidoximes and other possible products, such as ureas and cyanamides, have not been found [7; 8; 9; 10]. Besides the formation of 2-aminospiropyrazolinium structures in the class of \(\beta\)-aminopropioamidoxime derivatives via the Boulton-Katritzky intramolecular rearrangement mechanism, it also occurs during the hydrolysis of 3-(\(\beta\)-aminoethyl)-5-aryl-1,2,4-oxadiazoles at room temperature (r.t.) in H\({}_{2}\)O, DMF + H\({}_{2}\)O, and during HCl hydrolysis. Under the first two conditions, 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates are formed, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced hydrochlorides and 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride [11; 12]. Spiropyrazolines, also known as a spirocytic hydrazine moiety, are rigid asymmetric heterocyclic structures with a chirality axis and with possible centers of chirality of C-5 carbon atoms in the most-studied examples: 1,2-diazospiro- and 2,3-diazospiropyrazolines [13; 14] or the ammonium nitrogen atom N(+)-5 in the 1,5-diazospiropyrazolinium systems (Figure 1). There is evidence of tautomerism in the 1,2-diazospiropyrazolines group [15]. According to NMR spectral data and X-ray diffraction data, 2-aminospiropyrazolinium systems exist only in the form of one amino-imine tautomer; no spectral signs of other possible tautomers have been recorded: enamine-amine and  
Figure 1: Spiropyrazolines are asymmetric structures with a chirality axis and centers of chirality C-5 carbon atoms in 1,2-diazospiro- and 2,3-diazospiropyrazolines or the ammonium nitrogen atom N(+)-5 in 1,5-diazospiropyrazolinium systems. As we discovered, the biological screening of 2-aminospiropyrazolinium containing compounds for a number of in vitro biological activities revealed samples **a-i** with different types and levels of activity (Scheme 1). Thus, compound **a** has an antitubercular activity on sensitive (H37 Rv) and multidrug resistant (MDR) strains of _M. tuberculosis_, equal to the activity of the basic antitubercular drug rifampicin; compounds **b** and **c** have antidiabetic \(\alpha\)-glucosidase activity exceeding that of the reference drug acarbose [10; 12]; compounds **d-i** demonstrate pronounced antimicrobial activity on the following bacteria set: _Staphylococcus aureus_, _Escherichia coli_, and _Pseudomonas aeruginosa_; however, this activity did not reach the activity of the reference drug, gentamicin [11]. Thus, 2-aminospiropyrazolinium compounds, which exhibit high antitubercular and antidiabetic activity, are promising candidates for extended biological tests. At the same time, 2-aminospiropyrazolinium-containing compounds have not been studied at all in practice in fields beyond a biomedical scope when compared to another related class of compounds, azoniaspiroalkanes.