An easy and versatile access to 8-substituted isoquinolines

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)]


Published in:
Tetrahedron Letters, 31, 22, 3125-8
Year:
1990
Keywords:
Note:
CAN 115:279864
28-5
Heterocyclic Compounds (More Than One Hetero Atom)
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
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:




 Record created 2006-03-03, last modified 2018-01-27


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