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.

Intermolecular [5 + 1] cycloaddition between vinyl diazo compounds and tert-butyl nitrite leads to 1,2,3-triazine 1-oxides, which undergo dinitrogen extrusion to form isoxazoles in high yields under mild conditions

Organic letters

Intermolecular [5 + 1]-Cycloaddition between Vinyl Diazo Compounds and tert-Butyl Nitrite to 1,2,3-Triazine 1-Oxides and Their Further Transformation to Isoxazoles.

Paper

Intermolecular [5 + 1]-Cycloaddition between Vinyl Diazo Compounds and tert-Butyl Nitrite to 1,2,3-Triazine 1-Oxides and Their Further Transformation to Isoxazoles.

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