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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 6, pp 643–649 | Cite as

Rapid Boulton–Katritzky rearrangement of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles upon exposure to water and HCl

  • Lyudmila A. Kayukova
  • Asem B. Uzakova
  • Anna V. Vologzhanina
  • Kydyrmolla Akatan
  • Esbol Shaymardan
  • Sana K. Kabdrakhmanova
Article
  • 39 Downloads

Сhemical stability of 3-(2-aminoethyl)-5-substituted 1,2,4-oxadiazoles was studied with respect to Boulton–Katritzky rearrangement, which is known to produce planar pyrazolines and pyrazoles upon heating in DMF at 150°C or without solvent at 240°C. The reactivity of 5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles in one type of Boulton–Katritzky rearrangement was observed at room temperature in H2O, DMF + H2O, and in the presence of HCl. Hydrolysis of 3,5-disubstituted 1,2,4-oxadiazoles under the first two conditions gave 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium benzoates, while the action of HCl on 3,5-disubstituted 1,2,4-oxadiazoles produced their hydrochlorides along with 2-amino-1,5-diazaspiro[4.5]dec-1-en-5-ium chloride hydrate. Thus, the reaction afforded spiropyrazoline compounds instead of products with a planar structure.

Keywords

5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles spiropyrazolines Boulton–Katritzky rearrangement hydrolysis tendency to regroup 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Lyudmila A. Kayukova
    • 1
  • Asem B. Uzakova
    • 1
  • Anna V. Vologzhanina
    • 2
  • Kydyrmolla Akatan
    • 3
  • Esbol Shaymardan
    • 3
  • Sana K. Kabdrakhmanova
    • 3
  1. 1.A. B. Bekturov Institute of Chemical SciencesAlmatyKazakhstan
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  3. 3.S. Amanzholov East Kazakhstan State UniversityUst-KamenogorskKazakhstan

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