Novel Indole Chemistry in the Synthesis of Heterocycles
Gordon W. Gribble, Mark G. Saulnier, Erin T. Pelkey, Tara L.S. Kishbaugh, Yanbing Liu, Jun Jiang, Hernando A. Trujillo, Daniel J. Keavy, Deborah A. Davis, Sam C. Conway, Frank L. Switzer, Sujata Roy, Richard A. Silva, Judy A. Obaza-Nutaitis, Mukund P. Sibi, Nikolai V. Moskalev, Timothy C. Barden, Louis Chang, Wendy M. Habeski (nee Simon), Benjamin Pelcman, William R. Sponholtz, III, Ryan W. Chau, Brett D. Allison, Sarah D. Garaas, Michael S. Sinha, Meredeth A. McGowan, Matthew R. Reese and Karen S. Harpp
Pages 1493-1519 (27)
Indoles that are substituted at the 2- or 3-position with electron-withdrawing groups (nitro, phenylsulfonyl) undergo nucleophilic addition, 1,3-dipolar cycloaddition, and Diels-Alder reactions to give a variety of indoles, pyrroloindoles, and carbazoles. New methods for the synthesis of furo[3,4-b]indoles and the novel ring system furo[3,4- b]pyrrole are described for the first time. Diels-Alder reactions of furo[3,4-b]pyrroles afford indoles after dehydration of the primary cycloadducts. Efficient syntheses of both 2- and 3-nitroindoles from indole are reported, and the first generation and successful electrophilic trapping of a 2,3-dilithioindole has been achieved.
dihaloindoles, nitroindoles, nucleophilic addition, krapcho decarboethoxylation, marine natural products, diels-alder reactions
Department of Chemistry,Dartmouth College, Hanover, New Hampshire 03755 USA.