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Synthese einiger 8‐substituierter 2‐Methyl‐1,2,3,4‐tetrahydroisochinoline
Author(s) -
Rey Max,
Vergnani Tiziana,
Dreiding André S.
Publication year - 1985
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19850680704
Subject(s) - chemistry , isoquinoline , substituent , oxime , derivative (finance) , ring (chemistry) , medicinal chemistry , nitro , stereochemistry , organic chemistry , alkyl , financial economics , economics
Synthesis of Some 8‐Substituted 2‐Methyl‐1,2,3,4‐tetrahydroisoquinolines A 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 NH 2 ‐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 NO 2 ‐group in 5 ( Steps 4 and 7 ) were also studied.