Synfacts 2006(5): 0428-0428  
DOI: 10.1055/s-2006-934361
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Regioselective Synthesis of Dihydrophenanthridines, Benzazepinones and Benzoazocinones

Contributor(s): Victor Snieckus, Bärbel Wittel
E. L. Cropper, A. J. P. White, A. Ford, K. K. (M.) Hii*
Imperial College London, UK
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
21. April 2006 (online)

Significance

Efficient Pd-catalyzed regioselective synthesis of dihydrophenathridine or benz­azepinone and benzazocinone derivatives from 2-iodophenylamides, whose regioselectivity depends on choice of conditions, is reported. These intramolecular Heck reactions require the use of phosphine ligands of which PPh3 gave the highest yields of benzazepinone and benzazocinone products. On the other hand, in the absence of phosphine ligands (Jeffery conditions: T. Jeffery Tetrahedron 1996, 52, 10113-10130), a biaryl coupling reaction is observed to give the dihydrophenanthridine. For substrates with n = 1, the reaction affords quinolinone products in 87% yield.