Benzocinnoline N-oxides give azomethine ylides with dimethyl acetylenedicarboxylate at elevated temperatures, most probably by 1,3-dipolar cycloaddition which is unprecedented for azoxy compounds, followed by electrocyclic ring opening; this mechanism is confirmed for the same reactions of the closely related N-iminobenzocinnolinium ylides.
S. R. Challand, C. W. Rees and R. C. Storr, J. Chem. Soc., Chem. Commun., 1973, 837 DOI: 10.1039/C39730000837
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