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SPIROPYRAZOLINIUM COMPOUNDS AS A RESULT OF β-AMINOPROPIOAMIDOXIMES INTRAMOLECULAR REARRANGEMENTS

The monograph deals with unexpected rearrangements of β-aminopropioamidoxime derivatives, which form previously unknown spiropyrazolinium compounds. Recently we found that the 3,5-substituted 1,2,4-oxadiazoles, which are derivatives of β-aminopropioamidoximes, are of interest for practical medicine since they possess local anaesthetic, anti-tubercular and anti-diabetic properties. But when analyzing biological activity, it is necessary to take into account the chemical stability of the studied compounds. It turned out that 3,5-substituted 1,2,4-oxadiazoles taken for screening according to the Boughton–Katritzky rearrangement scheme are easily transformed into previously unknown spiropyrazolinium compounds and, thus, the pronounced biological activity observed in practice, should be attributed to them. In addition, when studying the reactivity of β-aminopropioamidoximes in the arylsulfochlorination reaction, it was found that salts (chlorides and arylsulfonates) of spiropyrazolinium compounds are instantly formed without isolating of the expected O-sulfoaryl-β-aminopropioamidoximes. The monograph describes this interesting structural feature of β-aminopropioamidoximes - to form spiropyrazolinium systems with a rich potential for biologically useful properties.