In situ vinylindole synthesis. Diels-Alder reactions with maleic anhydride and maleic acid to give tetrahydrocarbazoles and carbazoles

Wayland E. Noland; Guang Ming Xia; Kyle R. Gee; Michael J. Konkel; Mary J. Wahlstrom; John J. Condoluci; Dale L. Rieger

doi:10.1016/0040-4020(96)00152-4

In situ vinylindole synthesis. Diels-Alder reactions with maleic anhydride and maleic acid to give tetrahydrocarbazoles and carbazoles

Wayland E. Noland
, Guang Ming Xia
, Kyle R. Gee
, Michael J. Konkel
, Mary J. Wahlstrom
, John J. Condoluci
, Dale L. Rieger

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

Tetrahydrocarbazoles have been prepared in one-flask syntheses from indoles, ketones, and maleic anhydride, with acid catalysis. The reactions involve a condensation of the indole with the ketone or aldehyde, followed by an in situ trapping of the vinylindole in a Diels-Alder reaction with maleic anhydride. Depending on which indole is used, this may or may not be followed by a double bond isomerization. If the double bond isomerization doesn't occur, the adduct may or may not be acylated at the nitrogen by maleic anhydride. 1,2,3,4-Tetrahydrocarbazole-1,2-dicarboxylic anhydrides have been hydrolyzed to the 1,2-dicarboxylic acids in good yields. The corresponding 1,2-dicarboxylic acids have been regioselectively decarboxylated at the 1-position in excellent yields. New results with the use of maleic acid as the dienophile in this reaction are also discussed.

Original language	English (US)
Pages (from-to)	4555-4572
Number of pages	18
Journal	Tetrahedron
Volume	52
Issue number	13
DOIs	https://doi.org/10.1016/0040-4020(96)00152-4
State	Published - Mar 1996

Bibliographical note

Funding Information:
We axe grateful to E. I. duPont de Nemours and Company (MJC, 1983, 1986), to the Allied Corporation (MJC, 1984), and to the Shell Companies Foundation (MJC, 1987) for summer graduate fellowships; to the 3M Company for a Research Assistantship (GMX, 1984); and to the Wayland E. Noland Research Fellowship Fund for graduate fellowships to MJC and GMX and a post-doctoral fellowship to MJK. We also thank the Lando-SOHIO Program for an undergraduate summer fellowship (KRG, 1985).

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@article{46463d8c2cc041dd84e277636ffb8c93,

title = "In situ vinylindole synthesis. Diels-Alder reactions with maleic anhydride and maleic acid to give tetrahydrocarbazoles and carbazoles",

abstract = "Tetrahydrocarbazoles have been prepared in one-flask syntheses from indoles, ketones, and maleic anhydride, with acid catalysis. The reactions involve a condensation of the indole with the ketone or aldehyde, followed by an in situ trapping of the vinylindole in a Diels-Alder reaction with maleic anhydride. Depending on which indole is used, this may or may not be followed by a double bond isomerization. If the double bond isomerization doesn't occur, the adduct may or may not be acylated at the nitrogen by maleic anhydride. 1,2,3,4-Tetrahydrocarbazole-1,2-dicarboxylic anhydrides have been hydrolyzed to the 1,2-dicarboxylic acids in good yields. The corresponding 1,2-dicarboxylic acids have been regioselectively decarboxylated at the 1-position in excellent yields. New results with the use of maleic acid as the dienophile in this reaction are also discussed.",

author = "Noland, \{Wayland E.\} and Xia, \{Guang Ming\} and Gee, \{Kyle R.\} and Konkel, \{Michael J.\} and Wahlstrom, \{Mary J.\} and Condoluci, \{John J.\} and Rieger, \{Dale L.\}",

note = "Funding Information: We axe grateful to E. I. duPont de Nemours and Company (MJC, 1983, 1986), to the Allied Corporation (MJC, 1984), and to the Shell Companies Foundation (MJC, 1987) for summer graduate fellowships; to the 3M Company for a Research Assistantship (GMX, 1984); and to the Wayland E. Noland Research Fellowship Fund for graduate fellowships to MJC and GMX and a post-doctoral fellowship to MJK. We also thank the Lando-SOHIO Program for an undergraduate summer fellowship (KRG, 1985).",

year = "1996",

month = mar,

doi = "10.1016/0040-4020(96)00152-4",

language = "English (US)",

volume = "52",

pages = "4555--4572",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "13",

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TY - JOUR

T1 - In situ vinylindole synthesis. Diels-Alder reactions with maleic anhydride and maleic acid to give tetrahydrocarbazoles and carbazoles

AU - Noland, Wayland E.

AU - Xia, Guang Ming

AU - Gee, Kyle R.

AU - Konkel, Michael J.

AU - Wahlstrom, Mary J.

AU - Condoluci, John J.

AU - Rieger, Dale L.

N1 - Funding Information: We axe grateful to E. I. duPont de Nemours and Company (MJC, 1983, 1986), to the Allied Corporation (MJC, 1984), and to the Shell Companies Foundation (MJC, 1987) for summer graduate fellowships; to the 3M Company for a Research Assistantship (GMX, 1984); and to the Wayland E. Noland Research Fellowship Fund for graduate fellowships to MJC and GMX and a post-doctoral fellowship to MJK. We also thank the Lando-SOHIO Program for an undergraduate summer fellowship (KRG, 1985).

PY - 1996/3

Y1 - 1996/3

N2 - Tetrahydrocarbazoles have been prepared in one-flask syntheses from indoles, ketones, and maleic anhydride, with acid catalysis. The reactions involve a condensation of the indole with the ketone or aldehyde, followed by an in situ trapping of the vinylindole in a Diels-Alder reaction with maleic anhydride. Depending on which indole is used, this may or may not be followed by a double bond isomerization. If the double bond isomerization doesn't occur, the adduct may or may not be acylated at the nitrogen by maleic anhydride. 1,2,3,4-Tetrahydrocarbazole-1,2-dicarboxylic anhydrides have been hydrolyzed to the 1,2-dicarboxylic acids in good yields. The corresponding 1,2-dicarboxylic acids have been regioselectively decarboxylated at the 1-position in excellent yields. New results with the use of maleic acid as the dienophile in this reaction are also discussed.

AB - Tetrahydrocarbazoles have been prepared in one-flask syntheses from indoles, ketones, and maleic anhydride, with acid catalysis. The reactions involve a condensation of the indole with the ketone or aldehyde, followed by an in situ trapping of the vinylindole in a Diels-Alder reaction with maleic anhydride. Depending on which indole is used, this may or may not be followed by a double bond isomerization. If the double bond isomerization doesn't occur, the adduct may or may not be acylated at the nitrogen by maleic anhydride. 1,2,3,4-Tetrahydrocarbazole-1,2-dicarboxylic anhydrides have been hydrolyzed to the 1,2-dicarboxylic acids in good yields. The corresponding 1,2-dicarboxylic acids have been regioselectively decarboxylated at the 1-position in excellent yields. New results with the use of maleic acid as the dienophile in this reaction are also discussed.

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U2 - 10.1016/0040-4020(96)00152-4

DO - 10.1016/0040-4020(96)00152-4

M3 - Article

AN - SCOPUS:0029879716

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VL - 52

SP - 4555

EP - 4572

JO - Tetrahedron

JF - Tetrahedron

IS - 13

ER -

In situ vinylindole synthesis. Diels-Alder reactions with maleic anhydride and maleic acid to give tetrahydrocarbazoles and carbazoles

Abstract

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