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Efficient assembly of mono- and bis(1,2,4-oxadiazol-3-yl)furoxan scaffolds via tandem reactions of furoxanylamidoximes†
RSC Advances ( IF 3.9 ) Pub Date : 2015-05-20 00:00:00 , DOI: 10.1039/c5ra07295f
Leonid L. Fershtat 1, 2, 3, 4 , Ivan V. Ananyev 2, 3, 4, 5 , Nina N. Makhova 1, 2, 3, 4
Affiliation  

A general, facile, highly effective one-pot protocol for the synthesis of new types of heterocyclic systems incorporating mono- and bis(1,2,4-oxadiazol-3-yl)furoxan cores based on the tandem heterocyclization of furoxanylamidoximes with various aliphatic, aromatic, and heterocyclic carboxylic acid chlorides under very mild conditions (Cs2CO3, MeCN, 20 °C) has been developed. In addition, a solvent-free approach for the (1,2,4-oxadiazol-3-yl)furoxan synthesis by the reaction of furoxanylamidoximes with trimethyl orthoformate catalyzed by Sc(OTf)3 has been achieved. The advantages of step economy and scope make these reactions a powerful tool for assembling heterocyclic scaffolds of general chemistry and biomedical interest.

中文翻译:

通过 呋喃苯并酰胺基肟的串联反应有效组装单和双(1,2,4-恶二唑-3-基)呋喃聚糖支架

一种通用,简便,高效的一锅操作规程,用于基于呋喃西酰胺基肟与各种脂肪族化合物的串联杂环化反应,合成掺入单和双(1,2,4-恶二唑-3-基)呋喃核的新型杂环系统,已经开发了在非常温和的条件下(Cs 2 CO 3,MeCN,20°C)的芳族和杂环羧酸氯化物。此外,已经实现了一种无溶剂的方法,该方法用于通过呋喃酰胺基肟与Sc(OTf)3催化的原甲酸三甲酯反应合成(1,2,4-恶二唑-3-基)呋喃。步骤经济和作用范围的优势使这些反应成为组装具有通用化学和生物医学兴趣的杂环支架的强大工具。
更新日期:2015-05-20
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