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
* Author to whom correspondence should be addressed.
Received: 9 September 2010; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

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(11):7742-7749.

Chicago/Turabian Style

Sébastien, Bouclé; Jérôme, Guillard; Marie-Claude, Viaud-Massuard. 2010. "α-Lithiation and Electrophilic Substitution of 1,4,4-Trimethyl-3,4-dihydroquinolin-2-one." Molecules 15, no. 11: 7742-7749.

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