Regioselective formation of 1,2,4-triazoles by the reaction of amidrazones in the presence of diethyl azodicarboxylate and catalyzed by triethylamine

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Aly , A A , Hassan , A A , Mohamed , N K , Ramadan , M , Brown , A B , Abd El-Aal , A S , Bräse , S & Nieger , M 2019 , ' Regioselective formation of 1,2,4-triazoles by the reaction of amidrazones in the presence of diethyl azodicarboxylate and catalyzed by triethylamine ' , Molecular Diversity , vol. 23 , no. 1 , pp. 195-203 . https://doi.org/10.1007/s11030-018-9868-6

Title: Regioselective formation of 1,2,4-triazoles by the reaction of amidrazones in the presence of diethyl azodicarboxylate and catalyzed by triethylamine
Author: Aly, Ashraf A.; Hassan, Alaa A.; Mohamed, Nasr K.; Ramadan, Mohamed; Brown, Alan B.; Abd El-Aal, Amal S.; Bräse, Stefan; Nieger, Martin
Contributor: University of Helsinki, Department of Chemistry
Date: 2019-02
Language: eng
Number of pages: 9
Belongs to series: Molecular Diversity
ISSN: 1381-1991
URI: http://hdl.handle.net/10138/310814
Abstract: A general method for the synthesis of 1,3,5-trisubstituted 1,2,4-triazoles has been developed from reaction of amidrazones with ethyl azodicarboxylate and triethylamine (Mitsunobu reagent) in EtOH. This highly regioselective one-pot process provides rapid access to highly diverse triazoles. The reaction was explained, based on Mitsunobu reagent oxidizing ethanol to acetaldehyde, which would then react with amidrazones to give the substituted 3-methyltriazoles. A [2 + 3] cycloaddition reaction between two oxidized forms of amidrazones produced the second type of triazoles. X-ray structure analyses proved the structure of each type of product. [GRAPHICS] .
Subject: Amidrazones
Mitsunobu reagent
Regioselective
1,2,4-Triazoles
DIISOPROPYL AZODICARBOXYLATE
CHLORIDE
ACID
116 Chemical sciences
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