Department of Chemistry, The University of Texas at San Antonio, San Antonio, Texas 78249, United States.
Org Lett. 2021 Feb 5;23(3):925-929. doi: 10.1021/acs.orglett.0c04130. Epub 2021 Jan 8.
The formation of nitrile oxides with diazocarbonyl compounds by nitrosyl transfer from -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.
本文报道了在温和条件下，通过正丁基亚硝酰从-丁基亚硝酸酯中转移亚硝酰基，形成腈氧化物，而无需使用催化剂或添加剂。这种转化广泛适用于通过二聚作用合成呋咱，以及通过环加成合成异噁唑和异噁唑啉。该方法还应用于两种生物活性化合物的毫摩尔规模合成。通过实验证实了重氮乙酰胺形成腈氧化物的稳定性。
