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
L De Angelis, H Zheng, MT Perz, H Arman… - Organic …, 2021 - ACS Publications
Organic Letters, 2021•ACS Publications
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.
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.
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.
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