Luca De Angelis, Haifeng Zheng, Matthew T Perz
Aug 9, 2021
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Influential Citations
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Organic letters
Abstract
1,2,3-Triazine 1-oxides are formed by nitrosyl addition from tert-butyl nitrite to the vinylogous position of vinyl diazo compounds. This transformation, which is a formal intermolecular [5 + 1] cycloaddition, occurs under mild conditions, with high functional group tolerance and regioselectivity, and can be employed for late-stage functionalization. Upon heating at refluxing chlorobenzene temperature, these triazine-N-oxides undergo dinitrogen extrusion to form isoxazoles in very high yields.