1,3-Oxazines and Related Compounds. X. Ring Transformation of 1,3-Oxazin-4-ones into Pyridine Derivatives
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Ring transformations of 2-aryl-6-methyl-4H-1,3-oxazin-4-ones (1-3) with carbanions derived from various ketones, esters, lactones, and nitriles to give 3-acetyl-4,5,6-trisubstituted-2-pyridone derivatives 12 were explored. 1,3-Oxazin-4-ones (1-3) underwent initial attack of the carbanions at the 2-position of the ring to give the 2-substituted-2-aryl-3,4-dihydro-2H-1,3-oxazin-4-ones (9a-o). The dihydrooxazines (9a-g) bearing a quarternary-carbon substituent at the 2-position of the 1,3-oxazine ring were stable. In contrast, the dihydrooxazines (9h-o) which possess a tertiarycarbon substituent at the 2-position were converted into the ring-opened acetoacetamide derivatives (11) and subsequently recyclized to the corresponding 3-acetyl-2-pyridone derivatives (12).
- 社団法人日本薬学会の論文
- 1985-03-25
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