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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| Format: | Article |
| Language: | English |
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Frontiers Media S.A.
2019-05-01
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| Series: | Frontiers in Chemistry |
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| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00345/full |
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| author | Nikita E. Golantsov Hung M. Nguyen Alexandra S. Golubenkova Alexey V. Varlamov Erik V. Van der Eycken Erik V. Van der Eycken Leonid G. Voskressensky |
| author_facet | Nikita E. Golantsov Hung M. Nguyen Alexandra S. Golubenkova Alexey V. Varlamov Erik V. Van der Eycken Erik V. Van der Eycken Leonid G. Voskressensky |
| author_sort | Nikita E. Golantsov |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-04-13T07:48:42Z |
| format | Article |
| id | doaj.art-09cfc6232a2e488894f802a3ada31584 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-04-13T07:48:42Z |
| publishDate | 2019-05-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-09cfc6232a2e488894f802a3ada315842022-12-22T02:55:37ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-05-01710.3389/fchem.2019.00345456949Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and AlcoholsNikita E. Golantsov0Hung M. Nguyen1Alexandra S. Golubenkova2Alexey V. Varlamov3Erik V. Van der Eycken4Erik V. Van der Eycken5Leonid G. Voskressensky6Department of Organic Chemistry, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Moscow, RussiaDepartment of Organic Chemistry, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Moscow, RussiaDepartment of Organic Chemistry, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Moscow, RussiaDepartment of Organic Chemistry, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Moscow, RussiaDepartment of Organic Chemistry, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Moscow, RussiaLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Leuven, BelgiumDepartment of Organic Chemistry, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Moscow, RussiaA 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.https://www.frontiersin.org/article/10.3389/fchem.2019.00345/fullmulticomponent reactionsisocyanidesindoleninium ionsaryl(indol-3-yl)methylium ionsimidates |
| spellingShingle | Nikita E. Golantsov Hung M. Nguyen Alexandra S. Golubenkova Alexey V. Varlamov Erik V. Van der Eycken Erik V. Van der Eycken Leonid G. Voskressensky Three-Component Reaction of 3-Arylidene-3H-Indolium Salts, Isocyanides, and Alcohols Frontiers in Chemistry multicomponent reactions isocyanides indoleninium ions aryl(indol-3-yl)methylium ions imidates |
| 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 | multicomponent reactions isocyanides indoleninium ions aryl(indol-3-yl)methylium ions imidates |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00345/full |
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