Science of Synthesis

Parrain, J.-L.; Thibonnet, J., Science of Synthesis, (2005) 26, 817.

α-Alkoxy-α-amino ketones can be prepared by oxidation of the corresponding α-amino ketones using diverse oxidation conditions. Nevertheless, it is not a popular way to access the title compounds. This type of reaction is mainly used in heterocyclic chemistry. For example, N-acetyl-2-hydroxyindolones are prepared by oxidation of N-acetylindol-3-ones with an oxodiperoxomolybdenum–hexamethylphosphoric triamide complex.[‌411‌] Equally, N-tosyl-α-methoxyphenacylaniline is prepared from the corresponding aniline by manganese(IV) oxide promoted oxidation or photochemical oxidation in the presence of methanol.[‌412‌,‌413‌] Finally, the acetoxyisoquinoline-1,4-dione ‌229‌ is prepared by oxidation of ‌228‌ with lead(IV) acetate in dichloromethane in 80% yield. By elimination of acetic acid, ‌229‌ was found to be a good precursor of the corresponding cyclic acylimine (2-N-substituted quinone) ‌230‌, which gives hetero-Diels–Alder adducts ‌231‌ with conjugated dienes. By refluxing ‌229‌ with methanol, ethanol, or water, the corresponding 3-methoxy, 3-ethoxy, or 3-hydroxy derivatives are obtained in good yields (‌Scheme 96‌).[‌414‌]

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References

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• 8.Meeeee-Meee, (8888) M 88e8, 888.