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Synthesis of some alkaloid derivatives. XVII

I. Ježo, M. Karvaš, and K. Tihlárik

Slovak Academy of Sciences, Bratislava

Abstract: cf. CA 53, 20107a. The prepn. of derivs. of 6,7-dimethoxy-l,2,3,4-tetrahydroisoquinoline, substituted in positions 1,2,3 were described. These compds. were prepd.: (±)-N-carbamoylsalsolidine, m. 189-90° (EtOH); (±)-N-thiocarbamoylsalsolidine, m. 137-8° (EtOH); 3,4-dimethoxyphenylisopropylamine, b9 151-2°, n22D 1.5350; 1-(3,4-dimethoxyphenyl)-2-acetamidopropane, m. 85-6° (C₆H₆-petr. ether); 1-(3,4-dimethoxyphenyl)-2-benzyloxyacetamidopropane, m. 74-5° (C₆H₆-petr. ether); 1,3-dimethyl-6,7-dimethoxy-3,4-dihydroisoquinoline,-HCl, m. 224-5° (EtOH); 1-benzyloxymethyl-3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline-0.5H₂PtCl₆, m. 214-16° (EtOH); 1,3-dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-HCl, m. 269-70° (EtOH); 1-benzyloxymethyl-3-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-HCl, m. 243-5° (EtOH); 1-hydroxymethyl-3-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-HCl, m. 227-9° (EtOH); 2-methyl-4-(3,4-dimethoxybenzal)-5-oxazolone, m. 167° (EtOH); Me α-acetamido-3,4-dimethoxycinnamate, m. 196° (EtOH); Me α-acetamido-β-(3,4-dimethoxyphenyl)propionate, m. 110° (MeOH), 1-methyl-3-carbomethoxy-6,7-dimethoxy-3,4-dihydroisoquinoline-HCl, m. 210° (EtOH); 1-methyl-3-carbomethoxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-HCl, m. 233° (EtOH), 1-methyl-3-hydroxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline, m. 141°.

Full paper in Portable Document Format: 142a95.pdf (in Slovak)

Chemical Papers 14 (2) 95–104 (1960)