Syntheses of 1-(3-Hydroxy-4-methoxyphenethyl)-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline-6-ol and 1-(3-Hydroxy-4-methoxybenzyl)-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline-6, 8-diol and Attempt to cyclize the Isoquinoline Derivatives by Phenol Oxidation : Studies on the Syntheses of Heterocyclic Compounds. CCXXVIII

Abstract

Reaction of phenethylamine (XVII) and a carboxylic acid (XVIII) afforded the amide (XIX) which was converted to the amide (XX) and submitted to the Bischler-Napieralski reaction to prepare the 3, 4-dihydroisoquinoline compound (XXI). XXI was converted, via its methiodide (XXII) and 3'-hydroxyisoquinoline compound (XXIV), into 1-(3-hydroxy-4-methoxyphenethyl)-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinolin-6-ol (VIII). Another reaction of the amine (XXVII) and a carboxylic acid (XXVIII) afforded the amide (XXIX) whose Bischler-Napieralski reaction gave the 3, 4-dihydroisoquinoline compound (XXX), which was converted via its methiodide (XXXI) and the 2-methyl compound (XXXII) into 1-(3-hyrdoxy-4-methoxybenzyl)-7-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline-6, 8-diol (XI). The amide (XIX) was derived to the secondary amine (XXVI) via the amide (XXV) and debenzylation of XXVI afforded 3, 3'-dihydroxyamine (XV). Phenolic oxidative coupling was examined with the compounds so obtained, VIII, XI, and XV, but the reaction did not materialize.