Journal ArticleDOI
Proton-induced Diels-Alder reactions of 2-Vinylindoles
Siegfried Blechert,Thomas Wirth +1 more
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In this article, new induction methods for the Diels-Alder reaction of acceptor-substituted 2-vinylindoles with carbodienophiles are described.About:
This article is published in Tetrahedron Letters.The article was published on 1992-10-27. It has received 19 citations till now. The article focuses on the topics: Diene.read more
Citations
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Book ChapterDOI
Functionalization of Indole and Pyrrole Cores via Michael-Type Additions
TL;DR: The present review focuses only on the functionalization of indoles and the pyrroles via Michael additions because of the potential biological activity exhibited by these compounds.
Journal ArticleDOI
Synthesis of new 2-vinylation products of indole via a Michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles.
TL;DR: Reaction of 4,7-dihydroindole and dimethyl acetylenedicarboxylate provided a convenient route to functionalized 2-vinylindoles and their cycloadduct.
Journal ArticleDOI
Brønsted acid mediated tandem Diels-Alder/aromatization reactions of vinylindoles.
TL;DR: A Brønsted acid catalyzed tandem Diels-Alder/aromatization reaction of 2-vinylindoles has been developed that provides a highly efficient and concise approach to 3-indolyl-substituted tetrahydrocarbazoles with various substituents in high yields under mild conditions.
Journal ArticleDOI
Diels-alder reactions of 2-vinylindoles with open-chain C=C dienophiles
TL;DR: In this paper, the synthesis of diastereoisomeric 3,4-disubstituted 1,2,3, 4-tetrahydrocarbazoles by Diels-Alder cycloaddition reactions between [(E)-2-vinyl]indole-1-carboxylic acid ethyl esters and open-chain C=C dienophiles is reported and discussed.
Journal ArticleDOI
[4 + 2]-Cycloaddition Reactions between β-Acceptor-Substituted Enamines and 2-Vinylindole Radical Cations Acting as Hetero-Dienes
TL;DR: Cycloaddition reactions between 2-vinylindoles acting as hetero-dienes and beta-acceptor substituted cyclic and acyclic enamines can be induced by formation of 2-vindylindole radical cations either via anodic oxidation or photoelectron transfer (PET) using catalytic amounts of triarylpyrylium tetrafluoroborates as sensitizers.
References
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Journal ArticleDOI
Reactions of 2-vinylindoles with carbodienophiles: synthetic and mechanistic aspects
Manfred Eitel,Ulf Pindur +1 more
Journal ArticleDOI
Reactions on solid supports part IV: Reactions of αβ-unsaturated carbonyl compounds with indoles using clay as catalyst
TL;DR: In this article, a 3-benzyl substituent already present migrated to the 2-position, being displaced by the incoming electrophile, thus confirming that electrophilic substitution in indole occurs primarily at the 3-position.
Journal ArticleDOI
Hetero-cope rearrangements - vI1 short and stereoselective syntheses of 2-vinylindoles by a tandem-process
TL;DR: In this article, the initially formed N-phenylnitrone-intermediates are converted by a tandem reaction (cycloaddition, Cope rearrangement, retro-Michael addition, and indolization) to 2-vinylindoles.
Journal ArticleDOI
First Synthesis of 2-Vinylindole and its diels-Alder Reactions with CC-Dienophiles†‡
Ulf Pindur,Manfred Eitel +1 more
TL;DR: In this article, 2-vinylindole (2) was prepared by means of an intramolecular Wittig process, and the indole 2 functions as a heterocyclic, donor-activated 1,3-diene and undergoes cycloaddition reactions with dimethyl acetylenedicarboxylate, N-phenylmaleimide, and p-benzoquinone leading to the novel carbazole dervatives 3, 4, 5c, 6 and 7 respectively.
Journal ArticleDOI
Diels‐alder reactions of methyl‐ and π‐acceptor‐substituted 2‐vinylindoles with dimethyl acetylenedicarboxylate and tetracyanoethylene: Novel functionalized carbazoles
Ulf Pindur,Manfred Eitel +1 more
TL;DR: In this paper, the Diels-Alder reactions of the 2-vinylindoles with dimethyl acetylenedicarboxylate and tetracyanoethylene give rise to the novel 1,2-dihydro- and 1, 2,3,4-tetrahydrocarbazoles 2, 4, and 5 as well as the fully aromatized carbazoles 3.
Related Papers (5)
Reactions of 2-vinylindoles with carbodienophiles: synthetic and mechanistic aspects
Manfred Eitel,Ulf Pindur +1 more
Electron Transfer‐Catalyzed Diels–Alder Reactions with 2‐Vinylindoles
Olaf Wiest,Eberhard Steckhan +1 more