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. 2024 Jun 7;89(11):7780-7789.
doi: 10.1021/acs.joc.4c00448. Epub 2024 May 16.

Regioselective N-Trideuteromethylation of Tautomeric Polyaza Heterocycles

Jianxin Zhang  1 , Bowen Lei  1 , Mingrui Qin  1 , Tao Lei  1 , Ge Yang  1 , Junjie Liu  1 , Qianhui Liu  1 , Da-Jin Yang  2 , Shu-Feng Song  2 , Yudong Yang  1
Affiliations

Regioselective N-Trideuteromethylation of Tautomeric Polyaza Heterocycles

Jianxin Zhang et al. J Org Chem. .

Abstract

Methods for regioselective N-trideuteromethylation of tautomeric polyaza heterocycles are highly sought-after. Disclosed herein is an N-trideuterated methylation reaction of imidazoles and pyrazoles with high regioselectivity and deuterium purity using easily available CF3SO3CD3 as the -CD3 source. This method enables the easy synthesis of important deuterium-labeled azoles, including dimetridazole-d3, ipronidazole-d3, hydroxy dimetridazole-d3, and ronidazole-d3.

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