Electrocyclic Ring‐Opening of 1,2,4‐Oxadiazole[4,5‐a]piridinium Chloride: a New Route to 1,2,4‐Oxadiazole Dienamino Compounds

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 bic...

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Bibliographic Details
Published in:ChemistryOpen (Weinheim) 2019-09, Vol.8 (9), p.1209-1221
Main Authors: Carella, Stefano, Memeo, Misal Giuseppe, Quadrelli, Paolo
Format: Article
Language:English
Subjects:
1,3-dipolar cycloadditions
Amines
Ammonia
Bicarbonates
Chlorides
Chromatography
Derivatives
dienamino derivatives
Laboratories
nitrile oxides
NMR
Nuclear magnetic resonance
Nucleophiles
Oxadiazoles
Ring opening
Zincke salts
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Summary: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. Easy dienamines! 1,2,4‐Oxadiazole[4,5‐a]piridinium chloride undergoes nucleophilic addition of amines to afford 1,2,4‐oxadiazole dienamine 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.
ISSN:2191-1363
2191-1363
DOI:10.1002/open.201900230