Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols

A novel isocyanide-based multicomponent synthesis of alkyl aryl(indol-3-yl)acetimidates has been established. Starting from aryl(indol-3-yl)methylium tetrafluoroborates, aromatic isocyanides and alcohols, the imidates were obtained in moderate to very good yields. Consecutive four-component synthesi...

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Autores principales: Golantsov, Nikita E., Nguyen, Hung M., Golubenkova, Alexandra S., Varlamov, Alexey V., Van der Eycken, Erik V., Voskressensky, Leonid G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6532454/
https://www.ncbi.nlm.nih.gov/pubmed/31157211
http://dx.doi.org/10.3389/fchem.2019.00345
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author Golantsov, Nikita E.
Nguyen, Hung M.
Golubenkova, Alexandra S.
Varlamov, Alexey V.
Van der Eycken, Erik V.
Voskressensky, Leonid G.
author_facet Golantsov, Nikita E.
Nguyen, Hung M.
Golubenkova, Alexandra S.
Varlamov, Alexey V.
Van der Eycken, Erik V.
Voskressensky, Leonid G.
author_sort Golantsov, Nikita E.
collection PubMed
description A novel isocyanide-based multicomponent synthesis of alkyl aryl(indol-3-yl)acetimidates has been established. Starting from aryl(indol-3-yl)methylium tetrafluoroborates, aromatic isocyanides and alcohols, the imidates were obtained in moderate to very good yields. Consecutive four-component synthesis of the above mentioned imidates from N-alkylindoles, aromatic aldehydes, aromatic isocyanides and alcohols was also proposed. In addition, it was shown that in the presence of water, aryl(indol-3-yl)methylium tetrafluoroborates reacted with isocyanides to furnish aryl(indol-3-yl)acetamides.
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spelling pubmed-65324542019-05-31 Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols Golantsov, Nikita E. Nguyen, Hung M. Golubenkova, Alexandra S. Varlamov, Alexey V. Van der Eycken, Erik V. Voskressensky, Leonid G. Front Chem Chemistry A novel isocyanide-based multicomponent synthesis of alkyl aryl(indol-3-yl)acetimidates has been established. Starting from aryl(indol-3-yl)methylium tetrafluoroborates, aromatic isocyanides and alcohols, the imidates were obtained in moderate to very good yields. Consecutive four-component synthesis of the above mentioned imidates from N-alkylindoles, aromatic aldehydes, aromatic isocyanides and alcohols was also proposed. In addition, it was shown that in the presence of water, aryl(indol-3-yl)methylium tetrafluoroborates reacted with isocyanides to furnish aryl(indol-3-yl)acetamides. Frontiers Media S.A. 2019-05-16 /pmc/articles/PMC6532454/ /pubmed/31157211 http://dx.doi.org/10.3389/fchem.2019.00345 Text en Copyright © 2019 Golantsov, Nguyen, Golubenkova, Varlamov, Van der Eycken and Voskressensky. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Golantsov, Nikita E.
Nguyen, Hung M.
Golubenkova, Alexandra S.
Varlamov, Alexey V.
Van der Eycken, Erik V.
Voskressensky, Leonid G.
Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols
title Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols
title_full Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols
title_fullStr Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols
title_full_unstemmed Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols
title_short Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols
title_sort three-component reaction of 3-arylidene-3h-indolium salts, isocyanides, and alcohols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6532454/
https://www.ncbi.nlm.nih.gov/pubmed/31157211
http://dx.doi.org/10.3389/fchem.2019.00345
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