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The synthesis and reactions of 4-(2- and 3-thienyl)-tetrahydroisoquinolines
Authors:David E Tupper  Terrence M Hotten  William G Prowse
Abstract: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.
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