Some pharmacologically interesting 1-substitutied 1, 2, 3, 4-tetrahydroisoquinoline-6, 7-diols were synthesized by the two following methods ·(i) 1-Benzyl or 1-heterocyclic amide derivatives, (IIa, b, VIIa, b, c) were cyclized by the Bischler-Napieralski reaction to 6, 7-dimethoxy-3, 4-dihydroisoquinolines (IIIa, b and VIIIa, b, c). wihch were reduced, and demethylated to yield Ia, b, c, and XIIa, b, c ·(ii) Compounds (Ic, d, e, f, g, h and XIVa, b, c) were obtained by the Pictet-Spengler reaction of 3, 4-dihydroxyphenylethylamine (V) and sodium phenylglycidates (IVc, d, e, f, g, h) or heterocyclic aldehyds (XIIIa, b, c) ·1-(3, 4, 5-Trimethoxybenzyl)-1, 2, 3, 4-tetrahydroisoquinoline-6, 7-diol was found to be the most active bronchodilator.
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