- Aryl radical cyclizations of 1-(2′-bromobenzyl)isoquinolines with AIBN-Bu3SnH: Formation of aporphines and indolo[2,1-a]isoquinolines
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(matrix presented) 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-α-hydroxybenzyl)isoquinolines, were also found to give the corresponding oxoaporphines or oxyaporphines.
- Orito, Kazuhiko,Uchiito, Shiho,Satoh, Yoshitaka,Tatsuzawa, Takashi,Harada, Rika,Tokuda, Masao
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p. 307 - 310
(2007/10/03)
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