Open AccessElectrocyclic Ring‐Opening of 1,2,4‐Oxadiazole[4,5‐ a ]piridinium Chloride: a New Route to 1,2,4‐Oxadiazole Dienamino Compounds
Author(s) -
Carella Stefano,
Memeo Misal Giuseppe,
Quadrelli Paolo
Publication year - 2019
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201900230
Subject(s) - oxadiazole , pyridinium , chemistry , nucleophile , ring (chemistry) , chloride , bicarbonate , combinatorial chemistry , computational chemistry , organic chemistry , catalysis
1,2,4‐Oxadiazole[4,5‐ a ]piridinium chloride adds nucleophiles to undergo electrocyclic ring opening affording 1,2,4‐oxadiazole dienamino derivatives. These pyridinium salts represent a special class of Zincke salts that are prone to rearrange when treated with primary amines or in the presence of bicarbonate to give the pyridones. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4‐oxadiazole dienamine derivatives. The mechanism is also discussed in the light of NMR experiments and theoretical calculations.