Reactivity of Isocoumarins. II. Reaction of 1-Ethoxyisochroman with Nucleophilic Reagents

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概要

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• The C_<(1)>-position of 1-ethoxyisochroman (3) is very susceptible to attack by various nucleophilic reagents. Reaction of 3 with various alcohols, such as benzyl alcohols, N, N-dimethylaminoethanol and ethyl lactate, gave corresponding 1-alkoxyisochromans (5,7,8,and 9). Reaction of 3 with phenols, such as phenol and methyl p-hydroxybenzoate, gave 1-(hydroxyphenyl) isochromans (11,12,13,and 16). Some monoalkoxybenzenes were unreactive with 3 but 1,3-dimethoxybenzene gave corresponding 1-(dimethoxyphenyl) isochromans (14 and 15). Reaction of 3 with an emanine such as 1-morpholino-1-cyclohexene gave 2-(1-isochromanyl)-1-(4-morpholino) cyclohexene, which was hydrolyzed to give 2-(1-isochromanyl) cyclohexanone (17). Reaction of 3 with ketones, i. e., cyclohexanone and ethyl acetoacetate, gave 17 and ethyl α-(1-isochromanyl) acetoacetate (18), respectively.

• 公益社団法人日本薬学会の論文
• 1980-10-25

著者

• 大和 正利

  Faculty Of Pharmaceutical Sciences Okayama University

• 小林 利雄

  Faculty of Pharmaceutical Sciences, Kyushu University

• 石川 忠興

  Faculty Of Pharmaceutical Sciences Okayama University

• 小林 利雄

  Faculty Of Pharmaceutical Sciences Kyushu University

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