Catalyst-Free Formation of Nitrile Oxides and Their Further Transformations to Diverse Heterocycles,Organic Letters

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Catalyst-Free Formation of Nitrile Oxides and Their Further Transformations to Diverse Heterocycles
Organic Letters ( IF 4.9 ) Pub Date : 2021-01-08 , DOI: 10.1021/acs.orglett.0c04130
Luca De Angelis ₁ , Alexandra M. Crawford ₁ , Yong-Liang Su ₁ , Daniel Wherritt ₁ , Hadi Arman ₁ , Michael P. Doyle ₁

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The formation of nitrile oxides with diazocarbonyl compounds by nitrosyl transfer from tert-butyl nitrite under mild conditions and without the use of a catalyst or an additive is reported. This transformation is broadly applicable to the synthesis of furoxans by dimerization and isoxazoles and isoxazolines by cycloaddition. This methodology is also applied for the millimole-scale synthesis of two biologically active compounds. The formation of the nitrile oxide from a diazoacetamide is stable and confirmed experimentally.

中文翻译：

不含催化剂的丁腈氧化物的形成及其向多元杂环的进一步转化

据报道，在温和条件下且不使用催化剂或添加剂的情况下，由亚硝酸叔丁酯经亚硝酰基转移而与重氮羰基化合物形成腈氧化物。该转化广泛适用于通过二聚作用合成呋喃喃以及通过环加成反应合成异恶唑和异恶唑啉。该方法也适用于两种生物活性化合物的毫摩尔规模的合成。由重氮乙酰胺形成的腈氧化物是稳定的，并已通过实验证实。

更新日期：2021-02-05

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