Rearrangement in Dihydroresorcinol Derivatives. II. Synthesis of 3-Alkoxy and Hydroxy-2-cyclohexen-1-one Oximes

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概要

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• The synthetic methods for 3-alkoxy- (IIa, b, c and IIIa, b, c) and hydroxy-2-cyclohexen-1-one oximes (IVa, c) were established. Treatment of dihydroresorcinol (Ia), dihydroorcinol (Ib), dimedone (Ic) and their derivatives with hydroxylamine hydrochloride in methanol, ethanol and water afforded good yields of IIa, b, c, IIIa, b, c and IVa, c. The reaction mechanisms and configurations of the oximes are also mentioned. Inaddition, our experiments revealed that the Gittel's assignment on the product obtained the bytreatment of dimedone (Ic) and NH_2OH・HCl in ethanol was erronous, that is, the product was not 3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one oxime (IVc) assigned by him, but 3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one oxime (IIIc).

• 公益社団法人日本薬学会の論文
• 1971-03-25

著者

• 田村 恭光

  Faculty Of Pharmaceutical Sciences Osaka University

• 寺島 正直

  Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen University

• 北 泰行

  Faculty Of Pharmaceutical Sciences Osaka University

• 松高 佳子

  Faculty Of Pharmaceutical Sciences Osaka University

• 寺島 正直

  Faculty Of Pharmaceutical Sciences Higashi-nippon-gakuen University

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