Issue 15, 2019

Intramolecular electrochemical dehydrogenative N–N bond formation for the synthesis of 1,2,4-triazolo[1,5-a]pyridines

Abstract

A metal- and oxidant-free intramolecular dehydrogenative N–N bond formation has been developed under mild and scalable electrolytic conditions. Various valuable 1,2,4-triazolo[1,5-a]pyridines were synthesized efficiently from the readily available N-(2-pyridyl)amidines. The reactions were conducted in a simple undivided cell under constant current conditions with nBu4NBr as both the redox mediator and the electrolyte. This protocol was applied to the efficient synthesis of key intermediates for anti-diabetic compounds.

Graphical abstract: Intramolecular electrochemical dehydrogenative N–N bond formation for the synthesis of 1,2,4-triazolo[1,5-a]pyridines

Supplementary files

Article information

Article type
Communication
Submitted
06 Jun 2019
Accepted
10 Jul 2019
First published
12 Jul 2019

Green Chem., 2019,21, 4035-4039

Intramolecular electrochemical dehydrogenative N–N bond formation for the synthesis of 1,2,4-triazolo[1,5-a]pyridines

Y. Li, Z. Ye, N. Chen, Z. Chen and F. Zhang, Green Chem., 2019, 21, 4035 DOI: 10.1039/C9GC01895F

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