Aryl Radical Cyclizations of 1-(2‘-Bromobenzyl)isoquinolines with AIBN−Bu3SnH: Formation of Aporphines and Indolo[2,1-a]isoquinolines
Organic Letters2000Vol. 2(3), pp. 307–310
Citations Over TimeTop 14% of 2000 papers
Abstract
[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.
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