Syntheses of 1-Carboxy-1, 2, 3, 4-tetrahydroisoquinoline Derivatives, 6-Carboxy-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrophenanthridine Derivatives and 6-Carboxy-dibenzo[b, d]pyran Derivatives by Phenolic Cyclization (Studies on the Syntheses of Heterocyclic Compounds. DCLXIV)

Abstract

Phenolic cyclization of 3-hydroxyphenethylamine (XII), 1-(3-hydroxyphenyl)-2-aminoethanol (XIII), 2-(3-hydroxyphenyl) cyclohexylamine (XIV), and 2-(3-hydroxyphenyl) cyclohexanol (XV) with several ketocarboxylic acids gave 1-carboxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives (I-IV), 6-carboxy-1, 2, 3, 4, 4a, 5, 6, 10b-octahydrophenanthridine derivatives (V-VIII), and 6-carboxydibenzo[b, d]pyran derivatives (IX-XI), respectively, which were expected to show an anti-inflammatory activity. In these compounds 1-benzyl-1-carboxy-1, 2, 3, 4-tetrahydro-6-hydroxyisoquinoline (III) and 1-carboxy-1, 2, 3, 4-tetrahydro-6-hydroxy-1-methylisoquinoline (I) were found to have almost the same potent anti-inflammatory activity as phenylbutazone in the initial screening of carrageenin-induced paw edema.