Aminolysis of 3, 4-Dihydroisocoumarins

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Other Title
  • 3,4-Dihydroisocoumarin類のAminolysis
  • 3 4 Dihydroisocoumarinルイ ノ Aminolysis

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Abstract

Ammonolysis of 3, 4-dihydroisocoumarins to obtain 3, 4-dihydroisocarbostyrils was investigated. Heating of a solution of 8-deoxyphyllodulcin (3) or phyllodulcin (8), a 3, 4-dihydroisocoumarins having a phenyl group substituted at 3-position, in ethanolic ammonia gave the corresponding 3, 4-dihydroisocarbostyrils (1 or 2) and stilbenes (4 and 5 or 9). By the same reaction, agrimonolide (10) an 3-alkyl-3, 4-dihydroisocoumarins, gave only 3-alkyl-3, 4-dihydroisocarbostyril (11). Aminolysis of 3 with methylamine or N, N-dimethylaminoethylamine gave the corresponding 2-(2-N-alkylcarbamoylphenyl)-1-(3-hydroxy-4-methoxyphenyl) ethanols in a high yield, which gave the corresponding 2-alkyl-3, 4-dihydroisocarbostirils (14 or 15) by heating with 50% acetic acid containing 4% sulfuric acid.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 98 (11), 1498-1502, 1978

    The Pharmaceutical Society of Japan

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