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Two‐Step Procedure for the Synthesis of 1,2,3,4‐Tetrahydro‐quinolines
Author(s) -
Warsitz Michael,
Doye Sven
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001337
Subject(s) - chemistry , regioselectivity , intramolecular force , amination , structural isomer , intermolecular force , combinatorial chemistry , catalysis , medicinal chemistry , stereochemistry , organic chemistry , molecule
A new two‐step procedure that includes an initial regioselective intermolecular hydroaminoalkylation of ortho ‐chlorostyrenes with N ‐methylanilines and a subsequent intramolecular Buchwald–Hartwig amination gives direct access to 1,2,3,4‐tetrahydroquinolines. The hydroaminoalkylation reaction of the ortho ‐chlorostyrenes is catalyzed by a 2,6‐bis(phenylamino)pyridinato titanium complex which delivers the linear regioisomers with high selectivities. In addition, the formation of unexpected dihydroaminoalkylation products from styrenes and N ‐methylanilines is reported.