Aztequine and Related Compounds. III. : Synthesis of dl-1-(4-Bromo-3-hydroxybenzyl)-1, 2, 3, 4-tetrahydro-6-methoxy-2-methyl-7-isoquinolinol Studies on the Syntheses of Heterocyclic Compounds.CLXXXIV

Abstract

The acid chloride (VI) was derived to diazoketone by treatment with diazomethane, further derived to the homo-ester (VIIIa) according to the method of Newman and others, using silver benzoate, and fusion-condensation of VIIIa and 4-benzyloxy-3-methoxyphenethylamine gave N-(4-benzyloxy-3-methoxyphenethyl)-2-(3-benzyloxy-4-bromophenyl) acetamide (IX). This amide (IX) was submitted to the Bischler-Napieralski reaction to form the 3, 4-dihydro-isoquinoline derivative (X), reduced with sodium borohydride to 1, 2, 3, 4-tetrahydroisoquinoline derivative (XII), and submitted to the Eschweiler-Clarke reaction to obtain the objective compound (IIc). This latter compound was also obtained by rendering X ammonia alkaline, deriving the free base thereby obtained to its methiodide (XI) by treatment with methyl iodide, and its reduction with sodium borohydride. Debenzylation of IIc with 20% methanolic hydrochloric acid afforded the debenzylated compound (IIb), m.p.106∼108°.