α-Lithiation and electrophilic substitution of 1,4,4-trimethyl-3,4-dihydroquinolin-2-one

Bouclé Sébastien; Guillard Jérôme; Viaud-Massuard Marie-Claude

doi:10.3390/molecules15117742

α-Lithiation and electrophilic substitution of 1,4,4-trimethyl-3,4-dihydroquinolin-2-one

Molecules. 2010 Oct 29;15(11):7742-9. doi: 10.3390/molecules15117742.

Authors

Bouclé Sébastien¹, Guillard Jérôme, Viaud-Massuard Marie-Claude

Affiliation

¹ UMR CNRS 6239 GICC, Laboratoire de Chimie Organique & Thérapeutique, UFR des Sciences Pharmaceutiques, Université François Rabelais de Tours, 31 Avenue Monge, 37200 Tours, France.

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Hypoglycemic Agents / chemical synthesis*
Hypoglycemic Agents / chemistry*
Molecular Structure
Propylamines / chemistry*
Quinolines / chemical synthesis*
Quinolines / chemistry*

Substances

4,4-dimethyl-1,2,3,4-tetrahydroquinoline
Hypoglycemic Agents
Propylamines
Quinolines
diisopropylamine