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The synthesis and reactions of 4‐(2‐ and 3‐thienyl)‐tetrahydroisoquinolines
Author(s) -
Tupper David E.,
Hotten Terrence M.,
Prowse William G.
Publication year - 1996
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.5570330420
Subject(s) - thiophene , chemistry , electrophile , ring (chemistry) , metalation , electrophilic substitution , tetrahydroisoquinoline , substitution reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis
Tetrahydroisoquinoline derivatives substituted in the 4‐position by either a 2‐ or 3‐substituted thiophene ring have been synthesised. Simple electrophilic substitution reactions of these systems take place as expected in the α‐position of the thiophene ring. Metalation reactions are more complex and take place at the benzylic 4‐position of the tetrahydroisoquinoline nucleus in the case of the 2‐substituted thiophene derivatives or at either the thiophene α‐positions or the benzylic 4‐position depending on the nature of the attacking electrophile in the case of the 3‐substituted thiophene system.