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15.3.1.2.1.2 Method 2: From 2,1-Benzisoxazole

DOI: 10.1055/sos-SD-015-00689

Larsen, R. D.; Cai, D.Science of Synthesis, (200515449.

The reaction of 2,1-benzisoxazole (247) with ketones 248 or 3-phenylprop-2-ynol (phenylpropargyl alcohol) under mercury(II) sulfate catalysis at high temperatures affords quinolines.[‌557‌] The reaction pathway proceeds through an NO bridged intermediate which undergoes elimination to a 1-oxide followed by deoxygenation to the quinoline 249 (Scheme 80). Reduction of benzisoxazoles with samarium(II) iodide generates the corresponding 2-aminobenzophenone.[‌558‌] When this is carried out in the presence of acetophenone, a Friedländer-like condensation takes place to give the 2,4-diarylquinolines in good yield.

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