Diels-Alder reactions of fused 5-, 6- and 7-membered ring 2-vinylindoles: Synthesis of annulated tetrahydrocarbazoles

Wayland E. Noland; Ryan J. Herzig; Honnaiah Vijay Kumar; Venkata Srinivasarao Narina; Pavel K. Elkin; Karen I. Valverde; Briana L. Kim

doi:10.1016/j.tet.2017.09.025

Diels-Alder reactions of fused 5-, 6- and 7-membered ring 2-vinylindoles: Synthesis of annulated tetrahydrocarbazoles

Wayland E. Noland, Ryan J. Herzig, Honnaiah Vijay Kumar, Venkata Srinivasarao Narina, Pavel K. Elkin, Karen I. Valverde, Briana L. Kim

Chemistry (Twin Cities)

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

6 Scopus citations

Abstract

Scaffolds of tetrahydrocarbazoles are an important class of biologically active compounds found abundant in nature. In the present investigation, functionalized polycyclic tetrahydrocarbazoles were synthesized using Diels-Alder cycloaddition between fused 5-, 6- and 7-membered ring 2-vinylindoles and various dienophiles. The dienophiles used were N-phenylmaleimides, 1,4-naphthoquinone, and dimethyl acetylenedicarboxylate (DMAD). When 1,4-naphthoquinone was used as a dienophile, the 5-membered ring Diels-Alder adduct was obtained in the oxidized form, but this form was not observed in the case of 6- and 7-membered ring Diels-Alder adducts. The desired product yields ranged from 60–70% and the structure of final compounds were determined using 1D and 2D NMR analysis. ¹H NMR studies confirmed excellent diastereoselectivity (>99% de).

Original language	English (US)
Pages (from-to)	6341-6346
Number of pages	6
Journal	Tetrahedron
Volume	73
Issue number	44
DOIs	https://doi.org/10.1016/j.tet.2017.09.025
State	Published - Nov 2 2017

Bibliographical note

Funding Information:
The authors thank the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project. We are grateful to Dr. Kenneth J. Tritch and to all referees for constructive suggestions.

Publisher Copyright:
© 2017

Keywords

2-Vinylindoles
Diels-Alder
Tetrahydrocarbazoles

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10.1016/j.tet.2017.09.025

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title = "Diels-Alder reactions of fused 5-, 6- and 7-membered ring 2-vinylindoles: Synthesis of annulated tetrahydrocarbazoles",

abstract = "Scaffolds of tetrahydrocarbazoles are an important class of biologically active compounds found abundant in nature. In the present investigation, functionalized polycyclic tetrahydrocarbazoles were synthesized using Diels-Alder cycloaddition between fused 5-, 6- and 7-membered ring 2-vinylindoles and various dienophiles. The dienophiles used were N-phenylmaleimides, 1,4-naphthoquinone, and dimethyl acetylenedicarboxylate (DMAD). When 1,4-naphthoquinone was used as a dienophile, the 5-membered ring Diels-Alder adduct was obtained in the oxidized form, but this form was not observed in the case of 6- and 7-membered ring Diels-Alder adducts. The desired product yields ranged from 60–70% and the structure of final compounds were determined using 1D and 2D NMR analysis. 1H NMR studies confirmed excellent diastereoselectivity (>99% de).",

keywords = "2-Vinylindoles, Diels-Alder, Tetrahydrocarbazoles",

author = "Noland, {Wayland E.} and Herzig, {Ryan J.} and Kumar, {Honnaiah Vijay} and Narina, {Venkata Srinivasarao} and Elkin, {Pavel K.} and Valverde, {Karen I.} and Kim, {Briana L.}",

note = "Funding Information: The authors thank the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project. We are grateful to Dr. Kenneth J. Tritch and to all referees for constructive suggestions. Publisher Copyright: {\textcopyright} 2017",

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doi = "10.1016/j.tet.2017.09.025",

language = "English (US)",

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T1 - Diels-Alder reactions of fused 5-, 6- and 7-membered ring 2-vinylindoles

T2 - Synthesis of annulated tetrahydrocarbazoles

AU - Noland, Wayland E.

AU - Herzig, Ryan J.

AU - Kumar, Honnaiah Vijay

AU - Narina, Venkata Srinivasarao

AU - Elkin, Pavel K.

AU - Valverde, Karen I.

AU - Kim, Briana L.

N1 - Funding Information: The authors thank the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project. We are grateful to Dr. Kenneth J. Tritch and to all referees for constructive suggestions. Publisher Copyright: © 2017

PY - 2017/11/2

Y1 - 2017/11/2

N2 - Scaffolds of tetrahydrocarbazoles are an important class of biologically active compounds found abundant in nature. In the present investigation, functionalized polycyclic tetrahydrocarbazoles were synthesized using Diels-Alder cycloaddition between fused 5-, 6- and 7-membered ring 2-vinylindoles and various dienophiles. The dienophiles used were N-phenylmaleimides, 1,4-naphthoquinone, and dimethyl acetylenedicarboxylate (DMAD). When 1,4-naphthoquinone was used as a dienophile, the 5-membered ring Diels-Alder adduct was obtained in the oxidized form, but this form was not observed in the case of 6- and 7-membered ring Diels-Alder adducts. The desired product yields ranged from 60–70% and the structure of final compounds were determined using 1D and 2D NMR analysis. 1H NMR studies confirmed excellent diastereoselectivity (>99% de).

AB - Scaffolds of tetrahydrocarbazoles are an important class of biologically active compounds found abundant in nature. In the present investigation, functionalized polycyclic tetrahydrocarbazoles were synthesized using Diels-Alder cycloaddition between fused 5-, 6- and 7-membered ring 2-vinylindoles and various dienophiles. The dienophiles used were N-phenylmaleimides, 1,4-naphthoquinone, and dimethyl acetylenedicarboxylate (DMAD). When 1,4-naphthoquinone was used as a dienophile, the 5-membered ring Diels-Alder adduct was obtained in the oxidized form, but this form was not observed in the case of 6- and 7-membered ring Diels-Alder adducts. The desired product yields ranged from 60–70% and the structure of final compounds were determined using 1D and 2D NMR analysis. 1H NMR studies confirmed excellent diastereoselectivity (>99% de).

KW - 2-Vinylindoles

KW - Diels-Alder

KW - Tetrahydrocarbazoles

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Diels-Alder reactions of fused 5-, 6- and 7-membered ring 2-vinylindoles: Synthesis of annulated tetrahydrocarbazoles

Abstract

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