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Electrochemical synthesis of 1,2,4-triazole-fused heterocycles
Green Chemistry ( IF 9.8 ) Pub Date : 2018-02-27 , DOI: 10.1039/c7gc03739b
Zenghui Ye 1, 2, 3 , Mingruo Ding 1, 2, 3 , Yanqi Wu 2, 3, 4, 5 , Yong Li 1, 2, 3 , Wenkai Hua 1, 2, 3 , Fengzhi Zhang 1, 2, 3
Affiliation  

A reagent-free intramolecular dehydrogenative C–N cross-coupling reaction has been developed under mild electrolytic conditions. In this atom- and step-economical one-pot process, valuable 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic compounds could be synthesized efficiently from commercially available aliphatic or (hetero)aromatic aldehydes and 2-hydrazinopyridines. Various functional groups are compatible with this metal- and oxidant-free protocol which can be carried out on a gram scale easily. This novel method was applied to the synthesis of one of the top-selling drugs Xanax and late stage functionalization for generating chemical diversity in biologically relevant lead molecules.

中文翻译:

1,2,4-三唑稠合杂环的电化学合成

在温和的电解条件下已开发出无试剂的分子内脱氢C–N交叉偶联反应。在这种原子经济和一步经济的一锅法中,有价值的1,2,4-三唑并[4,3- a ]吡啶和相关的杂环化合物可以从可商购的脂族或(杂)芳族醛和2-肼基吡啶。各种官能团都与这种无金属和无氧化剂的方案兼容,可以轻松地以克为单位进行操作。这种新方法被应用于最畅销药物Xanax的合成和后期功能化,以在生物学相关的先导分子中产生化学多样性。
更新日期:2018-04-23
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