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Synthesis of 7 hydroxy 3 alkyl iso quinolones and 7 hydroxy 3 alkyl iso coumarins from 4 hydroxy homo phthalic acid

Synthesis of 7 hydroxy 3 alkyl iso quinolones and 7 hydroxy 3 alkyl iso coumarins from 4 hydroxy homo phthalic acid

Indian Journal of Chemistry Section B Organic Chemistry Including Medicinal Chemistry 17(4): 360-363

Pyridine-catalyzed acylation of 4-hydroxyhomophthalic acid with acetic, propionic and butyric anhydrides furnishes 4-acetyl-, 4-propionyl- and 4-butyroyl-7-hydroxy-isochroman-1, 3-diones (II) respectively. The isochromandiones (II) react with ammonia to give 3-methyl-, 3-ethyl- and 3-propyl-isoquinolones (VI) and with methyl, benzyl and ethanolamines to give N-methyl-, N-benzyl- and N-(.beta.-hydroxy)ethyl derivatives of these isoquinolones (VII, VIII and IX). The 4-acylisochromandiones (II) rearrange in the presence of concentrated sulfuric acid to give 3-methyl-, 3-ethyl- and 3-propyl-isocoumarins (III) and their 4-carboxy derivatives (IV) depending on the temperature of the reaction. The isocoumarins (III) and (IV) react with ammonia and the other amines to furnish the same isoquinolones (VI-VIII) as obtained from II. Reaction of hydroxylamine with the isocoumarins (III) and (IV) furnishes 2,7-dihydroxy-3-alkylisoquinolones, but that with the 4-acylisochromandiones (II) gives 4-carboxy derivatives of these isoquinolones.

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