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Updated: May 30, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
N2-Alkylation of 1,2,3-Triazoles with Ethers under Thermodynamical Control
Hui Zhang1, Zijian Zhang2, Lifang Tian2
1School of Chemistry and Chemical Engineering, Zhoukou Normal University, Wenchang Road, Zhoukou 466001, China.
Abstract:
Herein, a relay strategy incorporating oxidative cross dehydrogenative coupling (CDC) and N1- to N2-isomerization is disclosed for the formal N2-selective alkylation of triazoles with ethers under thermodynamic control conditions. By taking advantage of the different thermodynamical stabilities of N1- and N2-alkylated triazoles (3.65 kcal/mol), the initially formed N1-isomers can be in situ converted into their more stable N2-isomers when reaching thermodynamic equilibrium. PhI(OAc)2 has been discovered to function as both an oxidant for the CDC process and an efficient mediator for the isomerization step.
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