Current Organic Chemistry

Back

Novel Indole Chemistry in the Synthesis of Heterocycles

Author(s): 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, Karen S. Harpp.

Abstract:

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.

Keywords: dihaloindoles, nitroindoles, nucleophilic addition, krapcho decarboethoxylation, marine natural products, diels-alder reactions

Order Reprints Order Eprints Rights & PermissionsPrintExport

Article Details

VOLUME: 9
ISSUE: 15
Year: 2005
Page: [1493 - 1519]
Pages: 27
DOI: 10.2174/138527205774370487
Price: $58