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4‐substituted‐1,2,3,4‐tetrahydro‐3,3‐dimethylisoquinolines. II.
Author(s) -
Bobowski George,
Gottlieb Jeffrey M.
Publication year - 1982
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570190102
Subject(s) - chemistry , acylation , substituent , friedel–crafts reaction , borohydride , potassium , sodium borohydride , organic chemistry , medicinal chemistry , catalysis
A practical synthesis (Scheme I) is described for the preparation of a series of 4‐substituted‐3,3‐dimethyl‐1,2,3,4‐tetrahydroisoquinolines ( 3 ). Treatment of α‐(1‐amino‐1‐methylethyl)arylmethanols or α‐(1‐amino‐1‐methylethyl)heteroarylmethanols ( 5 ) with aromatic aldehydes gave imines 7 from which amino alcohols 8 were derived by reduction with potassium borohydride. Acid catalyzed cyclization of 8 yielded 3 . An acyl substituent was installed by Friedel‐Crafts acylation as a final step. The biological activities of 3a (1) are briefly described.