Abstract
Lithiation of N-(2,2-diethoxyethyl)benzylamines I (R = Me, PhCH2) and reaction with electrophiles followed by acid-catalyzed cyclization leads to isoquinolines II (R1 = Me, MeO, CH2OH, MeS, Cl, Br, iodo) in 37-75% yield. [on SciFinder (R)]
Details
Title
An easy and versatile access to 8-substituted isoquinolines
Author(s)
Simig, Gyula ; Schlosser, Manfred
Published in
Tetrahedron Letters
Volume
31
Issue
22
Pages
3125-8
Date
1990
ISSN
0040-4039
Note
CAN 115:279864
28-5
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
137115-25-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclocondensation of); 137115-23-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclocondensation of, isoquinolinium from); 7652-71-3P; 108261-07-0P; 137115-14-1P; 137115-15-2P; 137115-16-3P; 137115-17-4P; 137115-18-5P; 137115-19-6P; 137115-20-9P; 137115-21-0P; 137115-22-1P; 137115-24-3P; 137115-26-5P; 137115-27-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 120-14-9; 591-31-1 (3-Methoxybenzaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (sequential lithiation, electrophilic substitution, and conversion of, to isoquinoline deriv.); 67280-26-6; 137115-13-0 Role: RCT (Reactant), RACT (Reactant or reagent) (sequential lithiation, electrophilic substitution, and intramol. cyclocondensation of, isoquinolines from); 624-92-0 Role: RCT (Reactant), RACT (Reactant or reagent) (substitution reaction of, with lithiated (diethoxyethyl)benzylamine)
28-5
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
137115-25-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclocondensation of); 137115-23-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and intramol. cyclocondensation of, isoquinolinium from); 7652-71-3P; 108261-07-0P; 137115-14-1P; 137115-15-2P; 137115-16-3P; 137115-17-4P; 137115-18-5P; 137115-19-6P; 137115-20-9P; 137115-21-0P; 137115-22-1P; 137115-24-3P; 137115-26-5P; 137115-27-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 120-14-9; 591-31-1 (3-Methoxybenzaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (sequential lithiation, electrophilic substitution, and conversion of, to isoquinoline deriv.); 67280-26-6; 137115-13-0 Role: RCT (Reactant), RACT (Reactant or reagent) (sequential lithiation, electrophilic substitution, and intramol. cyclocondensation of, isoquinolines from); 624-92-0 Role: RCT (Reactant), RACT (Reactant or reagent) (substitution reaction of, with lithiated (diethoxyethyl)benzylamine)
Laboratories
LSCO
Record Appears in
Scientific production and competences > SB - School of Basic Sciences > SB Archives > LSCO - Laboratory of Organic Synthesis and Catalysis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date
2006-03-03