Reactions of 1,2,4‐Oxadiazole[4,5‐a]piridinium Salts with Alcohols: the Synthesis of Alkoxybutadienyl 1,2,4‐Oxadiazoles

Reactions of 1,2,4‐Oxadiazole[4,5‐a]piridinium Salts with Alcohols: the Synthesis of Alkoxybutadienyl 1,2,4‐Oxadiazoles

Abstract 1,2,4‐Oxadiazole[4,5‐a]piridinium salts add alcohols and alkoxides to undergo electrocyclic ring opening affording alkoxybutadienyl 1,2,4‐oxadiazole derivatives. The pyridinium salts represent a special class of Zincke salts that are prone to rearrange to give alkoxybutadienyl 1,2,4‐oxadiaz...

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Bibliographic Details
Main Authors: Dr. Mattia Moiola, Dr. Marco Leusciatti, Prof. Dr. Paolo Quadrelli
Format: Article
Language:English
Published: Wiley-VCH 2020-02-01
Series:ChemistryOpen
Subjects:
Nitrile oxides
1,3-dipolar cycloadditions
Zincke salts
oxadiazoles
alkoxybutadienyl derivatives
Online Access:https://doi.org/10.1002/open.201900376
Description
Summary:Abstract 1,2,4‐Oxadiazole[4,5‐a]piridinium salts add alcohols and alkoxides to undergo electrocyclic ring opening affording alkoxybutadienyl 1,2,4‐oxadiazole derivatives. The pyridinium salts represent a special class of Zincke salts that are prone to rearrange to give alkoxybutadienyl 1,2,4‐oxadiazoles when treated with suitable nucleophiles or, alternatively, to give pyridones in the presence of bicarbonate. The pivotal tuning of the experimental conditions leads to a straightforward synthesis of valuable 1,2,4‐oxadiazole derivatives. The mechanism is also discussed in the light of previous observations.
ISSN:2191-1363

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