Aryl radical cyclizations of 1-(2'-bromobenzyl)isoquinolines with AIBN-Bu3SnH: formation of aporphines and indolo
[reaction: see text] Radical cyclization of alkoxy-substituted 1-(2'-bromobenzyl)-3,4-dihydroisoquinolines 1 with AIBN-Bu3SnH gave 6a,7-dehydroaporphines 2 preferentially. A steric repulsion between the respective alkoxy groups at the 7- and 3'-positions gave 5,6-dihydroindolo[2,1-a]isoquinolines 3 in a "disfavored" 5-endo cyclization mode. Radical cyclizations of the related substrates, such as 1-(2'-bromobenzoyl)isoquinolines or 1-(2'-bromo-alpha-hydroxybenzyl)isoquinolines, were also found to give the corresponding oxoaporphines or oxyaporphines.
Orito
K
Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Japan.
Uchiito
S
Satoh
Y
Tatsuzawa
T
Harada
R
Tokuda
M