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
Current Organic Chemistry
Title: Novel Indole Chemistry in the Synthesis of Heterocycles
Volume: 9 Issue: 15
Author(s): Mukund P. Sibi, Karen S. Harpp, Matthew R. Reese, Meredeth A. McGowan, Michael S. Sinha, Sarah D. Garaas, Brett D. Allison, Ryan W. Chau, William R. Sponholtz, III, Benjamin Pelcman, Wendy M. Habeski (nee Simon), Louis Chang, Timothy C. Barden, Nikolai V. Moskalev, Gordon W. Gribble, Judy A. Obaza-Nutaitis, Richard A. Silva, Sujata Roy, Frank L. Switzer, Sam C. Conway, Deborah A. Davis, Daniel J. Keavy, Hernando A. Trujillo, Jun Jiang, Yanbing Liu, Tara L.S. Kishbaugh, Erin T. Pelkey and Mark G. Saulnier
Affiliation:
Keywords: dihaloindoles, nitroindoles, nucleophilic addition, krapcho decarboethoxylation, marine natural products, diels-alder reactions
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.
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Sibi P. Mukund, Harpp S. Karen, Reese R. Matthew, McGowan A. Meredeth, Sinha S. Michael, Garaas D. Sarah, Allison D. Brett, Chau W. Ryan, Sponholtz, III R. William, Pelcman Benjamin, Habeski (nee Simon) M. Wendy, Chang Louis, Barden C. Timothy, Moskalev V. Nikolai, Gribble W. Gordon, Obaza-Nutaitis A. Judy, Silva A. Richard, Roy Sujata, Switzer L. Frank, Conway C. Sam, Davis A. Deborah, Keavy J. Daniel, Trujillo A. Hernando, Jiang Jun, Liu Yanbing, Kishbaugh L.S. Tara, Pelkey T. Erin and Saulnier G. Mark, Novel Indole Chemistry in the Synthesis of Heterocycles, Current Organic Chemistry 2005; 9 (15) . https://dx.doi.org/10.2174/138527205774370487
DOI https://dx.doi.org/10.2174/138527205774370487 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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