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A Ruthenium‐Catalyzed Approach to the Friedländer Quinoline Synthesis
Author(s) -
Vander Mierde Hans,
Van Der Voort Pascal,
De Vos Dirk,
Verpoort Francis
Publication year - 2008
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.200701001
Subject(s) - chemistry , ruthenium , quinoline , catalysis , yield (engineering) , alcohol , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
In a modification of the Friedländer reaction, 2‐aminobenzyl alcohol is oxidatively cyclized with a variety of ketones to yield substituted quinolines. Of all the ruthenium catalysts that were tested for this reaction, the second‐generation Grubbs' catalyst gives the highest quinoline yield, in combination with KO t Bu as a base. The presence of a hydrogen acceptor is required to regenerate the catalyst. Also the reaction mechanism is discussed, and the results show that there are possibly two different pathways towards quinolines.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)