α-Lithiation and electrophilic substitution of 1,4,4-trimethyl-3,4-dihydroquinolin-2-one.
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.
UMR CNRS 6239 GICC, Laboratoire de Chimie Organique & Thérapeutique, UFR des Sciences Pharmaceutiques, Université François Rabelais de Tours, 31 Avenue Monge, 37200 Tours, France.
Bouclé
B
Sébastien
Guillard
G
Jérôme
Viaud-Massuard
VM
Marie-Claude
D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011437:Propylamines / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
C528892:4,4-dimethyl-1,2,3,4-tetrahydroquinoline; D007004:Hypoglycemic Agents; D011437:Propylamines; D011804:Quinolines; C007442:diisopropylamine