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Application of Phosphine-Phosphite Ligands in the Iridium Catalyzed Enantioselective Hydrogenation of 2-Methylquinoline
Molecules 2010, 15(11), 7742-7749; doi:10.3390/molecules15117742

α-Lithiation and Electrophilic Substitution of 1,4,4-Trimethyl-3,4-dihydroquinolin-2-one

, *  and
UMR CNRS 6239 GICC, Laboratoire de Chimie Organique & Thérapeutique, UFR des Sciences Pharmaceutiques, Université François Rabelais de Tours, 31 avenue Monge, 37200 Tours, France
* Author to whom correspondence should be addressed.
Received: 9 September 2010 / Revised: 27 October 2010 / Accepted: 28 October 2010 / Published: 29 October 2010
(This article belongs to the Section Organic Synthesis)
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Treatment of 1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one (2) with lithium diisopropylamide (LDA) followed by a wide range of electrophiles give the corresponding 4,4-dimethyl-3-substituted-3,4-dihydroquinolin-2-ones 3-13, providing a very mild electrophilic substitution of the 4,4-dimethyl-1,2,3,4-tetrahydroquinoline core.
Keywords: tetrahydroquinoline; electrophilic substitution; anti-diabetic agents tetrahydroquinoline; electrophilic substitution; anti-diabetic agents
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Sébastien, B.; Jérôme, G.; Marie-Claude, V.-M. α-Lithiation and Electrophilic Substitution of 1,4,4-Trimethyl-3,4-dihydroquinolin-2-one. Molecules 2010, 15, 7742-7749.

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