8-Methoxyisoquinoline derivatives through ortho-selective metalation of 2-(3-methoxyphenyl)ethylamine
Butyllithium in Et2O smoothly metalates 3-MeOC6H4CH2CH2NHCOCMe3 at the ortho position flanked by the two substituents. Subsequent reaction with DMF followed by acid catalyzed cyclization and redn. gives 8-methoxy-1,2,3,4-tetrahydroisoquinoline (I). [on SciFinder (R)]
1991
32
17
1965
6
CAN 115:92035
27-17
Heterocyclic Compounds (One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
3282-30-2 (Pivaloyl chloride) Role: RCT (Reactant), RACT (Reactant or reagent) (acylation with, of anisylethylamine); 2039-67-0 Role: RCT (Reactant), RACT (Reactant or reagent) (pivaloylation of); 135338-84-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclocondensation of); 24693-45-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. or methylation of); 24693-40-1P; 24693-46-7P; 34146-68-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 134699-74-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn., regioselective metalation and formylation of)
REVIEWED
EPFL