Synthesis of Benzo-fused Heterocycles by Intramolecular α-Arylation of Ketone Enolate Anions
JF Guastavino, RA Rossi
Index: Guastavino, Javier F.; Rossi, Roberto A. Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 460 - 472
Full Text: HTML
Citation Number: 18
Abstract
A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular α-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular CAr–CAr coupling led to the formation of five-and six-member benzo-fused heterocycles ( ...
Related Articles:
[Eisch, John J.; Galle, James E. Journal of Organic Chemistry, 1990 , vol. 55, # 16 p. 4835 - 4840]
[Nojima; Ohya; Kanno; Hirobe Chemical and Pharmaceutical Bulletin, 1982 , vol. 30, # 12 p. 4500 - 4506]
Ethylene dications substituted with electron-donating groups
[Ohwada, Tomohiko; Shudo, Koichi Journal of Organic Chemistry, 1989 , vol. 54, # 22 p. 5227 - 5237]
[Norman, David W.; Carraz, Charles A.; Hyett, David J.; Pringle, Paul G.; Sweeney, Joseph B.; Orpen, A. Guy; Phetmung, Hirrahataya; Wingad, Richard L. Journal of the American Chemical Society, 2008 , vol. 130, # 21 p. 6840 - 6847]
[Fu, J.-m.; Sharp, M.J.; Snieckus, V. Tetrahedron Letters, 1988 , vol. 29, # 43 p. 5459 - 5462]