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16.12.2.2.3.3 Variation 3: Reaction of 1,3-Oxazin-4-one with Thioamides

DOI: 10.1055/sos-SD-016-00463

von Angerer, S.Science of Synthesis, (200416482.

Treatment of 6-methyl-2-phenyl-4H-1,3-oxazin-4-one with various thioamides in the presence of sodium hydride affords 6-substituted 5-acetylpyridin-4-ols 356 in good yields whereas the use of the corresponding amides results in far lower yields (Scheme 190).[‌440‌] This ring conversion can formally be regarded as a CNCC+NC pyrimidine-forming reaction.

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