Journal ArticleDOI
Tandem transformations of N-alkyl-N-allenylmethylanilines to N-alkyl-2-ethenylindoles
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TLDR
In this article, N-alkyl-N-allenylmethylanilines with magnesium monoperoxyphthalate in methanol-water underwent tandem transformations to furnish Nalkyl 2-ethenylindoles in good yield.Abstract:
Treatment of N-alkyl-N-allenylmethylanilines with magnesium monoperoxyphthalate in methanol–water underwent tandem transformations to furnish N-alkyl-2-ethenylindoles in good yield.read more
Citations
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Journal ArticleDOI
Isolation and synthesis of biologically active carbazole alkaloids
Journal ArticleDOI
Rearrangement of N-Oxyenamines and Related Reactions
Andrey A. Tabolin,Sema L. Ioffe +1 more
TL;DR: Direct α-Oxygenation of Carbonyl Compounds Reaction of carbonyl compounds with secondary amines is a classical method for enamine synthesis and was used in the syntheses of substituted anilines, quinolines, and other heteroaromatics as well as in the total synthesis of miltirone, sanguinarine, and chelerythrine.
Journal ArticleDOI
Synthesis and anticancer activity of new pyrrolocarbazoles and pyrrolo-β-carbolines
Marie Laronze,Michel Boisbrun,Stéphane Léonce,Bruno Pfeiffer,Pierre Renard,Olivier Lozach,Laurent Meijer,Amélie Lansiaux,Christian Bailly,Janos Sapi,J.-Y. Laronze +10 more
TL;DR: In this paper, pyrrolidino-fused (aza) carbazoles were prepared and screened towards a few cancer-related targets, including 28a and 28a derivatives.
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.
References
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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
Dimerization of 2-vinyl indoles and their alcohol precursors
Journal ArticleDOI
One-flask, consecutive [3,3]- and [2,3]-sigmatropic rearrangements for conversions of propargylic alcohols into 2-carbon-extended 4-oxo-2-alkenoate esters. Use of a new 1-chloro-1-ethoxy-2-sulfinylethylene
TL;DR: In this paper, seven differently substituted primary and secindary propargylic alcohols were shown to react with (arylsulfinyl)vinylic chloride at 100°C for 1h sequentially via a [3.3]sigmatropic rearrangement and then a [2.3]-sigmoid rearrange to form 4-oxo-2alkenoates.
Journal ArticleDOI
The reactivity of 2-vinylindoles with dimethyl acetylenedicarboxylate
TL;DR: In this paper, the Steric interaction between the N-methyl group on the indole ring and the 1-substituent on the ethenyl group prevents the diene system adopting a coplanar cisoid configuration and thereby, inhibits the π4 + π2 cycloaddition reaction of the system with dimethyl acetylenedicarboxylate.
Journal ArticleDOI
[2,3]-Sigmatropic rearrangement of .beta.-phenylsulfonyl propargylic sulfenates as a method for preparing 1,4-bis(phenylsulfonyl)-1,3-butadienes
Xiaoheng Wang,Zhijie Ni,Xiujing Lu,Andrea Hollis,Harold D. Banks,Augusto Rodriguez,Albert Padwa +6 more
TL;DR: In this article, several β-sulfoxy-substituted acetylenic carbinols were derived from thiyl radical attack at the olefinic bond to generate a propargylic radical.
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New Diels-Alder reactions with vinylindoles: a regio- and stereocontrolled access to annellated indoles and derivatives
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Olaf Wiest,Eberhard Steckhan +1 more