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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

UMR CNRS 6239 GICC, Laboratoire de Chimie Organique & Thérapeutique, UFR des Sciences Pharmaceutiques, Université François Rabelais de Tours, 31 avenue Monge, 37200 Tours, France
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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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Abstract

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 3.0).

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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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