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26.8.4.7 Synthesis via Cycloaddition of Arynes

DOI: 10.1055/sos-SD-126-00085

Sellars, J. D.Science of Synthesis Knowledge Updates, (20141441.

Arynes generated from ortho-silylaryl trifluoromethanesulfonates on treatment with cesium fluoride react smoothly with aryl dimethylhydrazones to generate aryl ketones possessing an ortho-dimethylamino group (Scheme 64).[‌180‌] Interestingly, this methodology is exploited to produce a naturally occurring acridone which, when demethylated, exhibits anti-HIV activity.

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References


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