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

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

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...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 54; no. 6; pp. 643 - 649
Main Authors: Kayukova, Lyudmila A., Uzakova, Asem B., Vologzhanina, Anna V., Akatan, Kydyrmolla, Shaymardan, Esbol, Kabdrakhmanova, Sana K.
Format: Journal Article
Language:English
Published: New York Springer US 01-06-2018
Springer
Springer Nature B.V
Subjects:
Aromatic compounds
Benzoates
Chemistry
Chemistry and Materials Science
Hydrochlorides
Organic Chemistry
Oxadiazoles
Pharmacy
spiropyrazolines
tendency to regroup
Boulton–Katritzky rearrangement
hydrolysis
5-aryl-3-[2-(piperidin-1-yl)ethyl]-1,2,4-oxadiazoles
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Summary: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 H 2 O, DMF + H 2 O, 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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-018-2321-z