Skip to Content
Merck
CN
  • α-Lithiation and electrophilic substitution of 1,4,4-trimethyl-3,4-dihydroquinolin-2-one.

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

Molecules (Basel, Switzerland) (2010-11-03)
Bouclé Sébastien, Guillard Jérôme, Viaud-Massuard Marie-Claude
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Diisopropylamine, puriss. p.a., ≥99.0% (GC)
Supelco
Diisopropylamine, analytical standard
Sigma-Aldrich
Diisopropylamine, ≥99.5%
Sigma-Aldrich
Lithium diisopropylamide solution, 2.0 M in THF/heptane/ethylbenzene
Sigma-Aldrich
Diisopropylamine, purified by redistillation, 99.95%