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Synthesis of 4-(1-alkenyl)isoquinolines by palladium(II)-catalyzed cyclization/olefination
Qinhua Huang1, Richard C Larock
1Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
The Journal of Organic Chemistry
|February 1, 2003
Abstract:
A variety of 4-(1-alkenyl)-3-arylisoquinolines have been prepared in moderate to excellent yields by the Pd(II)-catalyzed cyclization of 2-(1-alkynyl)arylaldimines in the presence of various alkenes. The introduction of an o-methoxy group on the arylaldimine promotes the Pd-catalyzed cyclization and stabilizes the resulting Pd(II) intermediate, improving the yields of the isoquinoline products. Ketone-containing isoquinolines 36 and 49-51 have also been prepared by this process when unsaturated alcohols are employed as the alkenes.