First Synthesis of 2‐Vinylindole and its diels‐Alder Reactions with CC‐Dienophiles
- 10 August 1988
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 71 (5) , 1060-1064
- https://doi.org/10.1002/hlca.19880710517
Abstract
By means of an intramolecular Wittig process, 2‐vinylindole (2) was prepared. The indole 2 functions as a heterocyclic, donor‐activated 1,3‐diene and undergoes [4+2] cycloaddition reactions with dimethyl acetylenedicarboxylate, N‐phenylmaleimide, and p‐benzoquinone leading to the novel carbazole dervatives 3, 4, 5c, 6 and 7 respectively. The reaction of 2 with acceptor (A)‐Substituted dienophiles (e.g.) ACHCH2, AC≡(CH) does not yield products that can be isolated.This publication has 14 references indexed in Scilit:
- New Reactions of 3‐Vinyl‐ and 3‐(2‐Propenyl)Indoles with N‐Phenylmaleimide: [4 + 2] Cycloaddition, ene reaction, and dimerizationHelvetica Chimica Acta, 1988
- New Reractions of 2-Vinylindoles with Azodienophiles: Diels-Alder Reaction versus Michael-type AdditionHETEROCYCLES, 1988
- Isomerisierung der Dihydropentalene und Umsetzung mit TetracyanethylenEuropean Journal of Inorganic Chemistry, 1987
- Diels‐Alder‐Reaktionen von 2′‐substituierten 3‐Vinyl‐1H‐indolen zu neuen anellierten Indol‐und Carbazol‐DerivatenHelvetica Chimica Acta, 1987
- Synthesis and [4 + 2]-Cycloadditions ofN-Phenylsulfonyl-3-vinylindoleSynthesis, 1986
- New synthesis of indoles from o-acylaminobenzyltriphenylphosphonium saltsJournal of the Chemical Society, Chemical Communications, 1981
- Mechanistic Aspects of Diels‐Alder Reactions: A Critical SurveyAngewandte Chemie International Edition in English, 1980
- Mechanistische Aspekte der Diels-Alder-Reaktion: Ein kritischer RückblickAngewandte Chemie, 1980
- The Wittig Reaction of Indole-2-methyltriphenylphosphonium Iodide with 4-Piperidone Derivatives and Aromatic AldehydesCanadian Journal of Chemistry, 1973
- Recognition of stereochemical paths by orbital interactionAccounts of Chemical Research, 1971