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Synfacts 2006(5): 0432-0432  
DOI: 10.1055/s-2006-934374
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Rh-Catalyzed C-H Addition of Quinazolines to Alkenes

Contributor(s): Victor Snieckus, Oleg M. Demchuk
S. H. Wiedemann, J. A. Ellman*, R. G. Bergman*
University of California at Berkeley, USA
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Publication History

Publication Date:
21 April 2006 (online)

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Significance

An elegant direct Rh-catalyzed addition of unactivated acyclic and cyclic olefins to dihydroquinazolines A and quinazoline D has been developed. The reaction proceeds via Rh-promoted C-H activation followed by alkene addition ­under mild conditions to give products B and C in good to excellent yields. An intramolecular version, E → F, was also reported and the method was applied to the synthesis of Vasicoline (6 steps, 8% overall yield), an alkaloid isolated from Adhatoda vasica, which exhibits antimalarial, antiinflammatory, and antitumor activity.