Crystal structure and antidiabetic activity of 2-aminospiropyrazolinium tosylates and the product of O-tosylation of β-(benzimidazol-1-yl)propioamidoxime.

2-Amino-1,5-diazaspiro[4.5]dec-1-en-5-ium salts possess bioactivity tuned by the nature of the heteroatoms in the six-membered ring and the counter-ion. The molecular environment of these cations in solids provides an opportunity to establish the conformations and hydrogen-bonding patterns typical for this family.

Redetermination of the structure of 2-amino-8-thia-1,5-di-aza-spiro-[4.5]dec-1-en-5-ium chloride monohydrate.

The reaction of β-(thio-morpholin-1-yl)propio-amidoxime with tosyl chloride in CHCl in the presence of DIPEA when heated at 343 K for 8 h afforded the title hydrated salt, CHNS·Cl·HO, in 84% yield. This course of the tosyl-ation reaction differs from the result of tosyl-ation obtained for this substrate at room temperature, when only 2-amino-8-thia-1,5-di-aza-spiro-[4.5]dec-1-ene-5-ammonium tosyl-ate was isolated in 56% yield.