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; Loius Chang; Wendy M. Habeski; Benjamin Pelcman; William R. Sponholtz; Ryan W. Chau; Brett D. Allison; Sarah D. Garaas; Michael S. Sinha; Meredeth A. McGowan; Matthew R. Reese; Karen S. Harpp

doi:10.2174/138527205774370487

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, Loius Chang, Wendy M. Habeski, Benjamin PelcmanWilliam R. Sponholtz, Ryan W. Chau, Brett D. Allison, Sarah D. Garaas, Michael S. Sinha, Meredeth A. McGowan, Matthew R. Reese, Karen S. Harpp

Research output: Contribution to journal › Review article › peer-review

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.

Original language	English (US)
Pages (from-to)	1493-1519
Number of pages	27
Journal	Current Organic Chemistry
Volume	9
Issue number	15
DOIs	https://doi.org/10.2174/138527205774370487
State	Published - Oct 2005
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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Gribble, G. W., Saulnier, M. G., Pelkey, E. T., Kishbaugh, T. L. S., Liu, Y., Jiang, J., Trujillo, H. A., Keavy, D. J., Davis, D. A., Conway, S. C., Switzer, F. L., Roy, S., Silva, R. A., Obaza-Nutaitis, J. A., Sibi, M. P., Moskalev, N. V., Barden, T. C., Chang, L., Habeski, W. M., ... Harpp, K. S. (2005). Novel indole chemistry in the synthesis of heterocycles. Current Organic Chemistry, 9(15), 1493-1519. https://doi.org/10.2174/138527205774370487

Gribble, GW, Saulnier, MG, Pelkey, ET, Kishbaugh, TLS, Liu, Y, Jiang, J, Trujillo, HA, Keavy, DJ, Davis, DA, Conway, SC, Switzer, FL, Roy, S, Silva, RA, Obaza-Nutaitis, JA, Sibi, MP, Moskalev, NV, Barden, TC, Chang, L, Habeski, WM, Pelcman, B, Sponholtz, WR, Chau, RW, Allison, BD, Garaas, SD, Sinha, MS, McGowan, MA, Reese, MR & Harpp, KS 2005, 'Novel indole chemistry in the synthesis of heterocycles', Current Organic Chemistry, vol. 9, no. 15, pp. 1493-1519. https://doi.org/10.2174/138527205774370487

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title = "Novel indole chemistry in the synthesis of heterocycles",

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.",

author = "Gribble, {Gordon W.} and Saulnier, {Mark G.} and Pelkey, {Erin T.} and Kishbaugh, {Tara L.S.} and Yanbing Liu and Jun Jiang and Trujillo, {Hernando A.} and Keavy, {Daniel J.} and Davis, {Deborah A.} and Conway, {Sam C.} and Switzer, {Frank L.} and Sujata Roy and Silva, {Richard A.} and Obaza-Nutaitis, {Judy A.} and Sibi, {Mukund P.} and Moskalev, {Nikolai V.} and Barden, {Timothy C.} and Loius Chang and Habeski, {Wendy M.} and Benjamin Pelcman and Sponholtz, {William R.} and Chau, {Ryan W.} and Allison, {Brett D.} and Garaas, {Sarah D.} and Sinha, {Michael S.} and McGowan, {Meredeth A.} and Reese, {Matthew R.} and Harpp, {Karen S.}",

year = "2005",

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doi = "10.2174/138527205774370487",

language = "English (US)",

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T1 - Novel indole chemistry in the synthesis of heterocycles

AU - Gribble, Gordon W.

AU - Saulnier, Mark G.

AU - Pelkey, Erin T.

AU - Kishbaugh, Tara L.S.

AU - Liu, Yanbing

AU - Jiang, Jun

AU - Trujillo, Hernando A.

AU - Keavy, Daniel J.

AU - Davis, Deborah A.

AU - Conway, Sam C.

AU - Switzer, Frank L.

AU - Roy, Sujata

AU - Silva, Richard A.

AU - Obaza-Nutaitis, Judy A.

AU - Sibi, Mukund P.

AU - Moskalev, Nikolai V.

AU - Barden, Timothy C.

AU - Chang, Loius

AU - Habeski, Wendy M.

AU - Pelcman, Benjamin

AU - Sponholtz, William R.

AU - Chau, Ryan W.

AU - Allison, Brett D.

AU - Garaas, Sarah D.

AU - Sinha, Michael S.

AU - McGowan, Meredeth A.

AU - Reese, Matthew R.

AU - Harpp, Karen S.

PY - 2005/10

Y1 - 2005/10

N2 - 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.

AB - 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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Novel indole chemistry in the synthesis of heterocycles

Abstract

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