4.4 Article

3-cyanomethyl-2-vinylindoles as thermal indole-2,3-quinodimethane equivalents: synthesis of functionalized 1,2,3,4-tetrahydrocarbazoles

Journal

TETRAHEDRON LETTERS
Volume 43, Issue 44, Pages 7925-7928

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)01907-X

Keywords

Diels-Alder reaction; 3-cyanomethyl-2-vinylindole; indole-2,3-quinodimethane; [1,5]-sigmatropic hydrogen shift; tetrahydrocarbazoles

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Electron-donating substituted 3-cyanomethyl-2-vinylindoles were found to rearrange via thermal [1,5]H shift into the corresponding indole-2,3-quinodimethanes which were trapped by dienophiles to afford tetrahydrocarbazoles. (C) 2002 Elsevier Science Ltd. All rights reserved.

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