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Larsen, R. D.; Cai, D., Science of Synthesis, (2005) 15, 449.
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 N—O 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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8-Meeeeeeeeeeeeee-8-eeeeeeeeeeee (888, M8 = MMM; M8 = Me); Meeeeee Meeeeeeee:[888]
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References
[557] | Meee, M.; Meeeee, M.; Meeeeeee, M., Meeeee Meeeeee Mee. Meee., (8888) 888, 888. |
[558] | Mee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
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- 8.Meeeee-Meee, (8888) M 8e, 888.