Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Synthesis of Some 8-Substituted 2-Methyl-1,2,3,4-tetrahydroisoquinolinesA general route to 8-substituted tetrahydroisoquinolines is exemplified by the preparation of the 2-methyl-1,2,3,4-tetrahydroisoquinolin-8-ol (11), the -8-carbaldehyde oxime (12) and the -8-carbonitrile (13). It involves the conversion of isoquinoline (1) by partially modified Steps 1, 2, 3, and 5 (see the Scheme) into the 5-bromo-8-nitro derivative 5, reduction of the latter to the 8-amino derivative 8 and replacement of the NH2-group with an appropriate substituent by a Sandmeyer-like reaction. The selective reductions of the N-containing ring in 6 (Steps 5, 6, and 8) and of the NO2-group in 5 (Steps 4 and 7) were also studied.
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