FeCl3 catalyzed intermolecular reaction between enol ethers and anilines: Access to 2,3-substituted indoles through aryl group migration

Jena, Tapan Kumar and Khan, Faiz Ahmed (2020) FeCl3 catalyzed intermolecular reaction between enol ethers and anilines: Access to 2,3-substituted indoles through aryl group migration. Tetrahedron Letters, 61 (49). p. 152583. ISSN 00404039

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Abstract

An intermolecular FeCl3 catalyzed reaction between anilines and enol ethers is described. A variety of enol ethers and aromatic amines undergo a C[sbnd]C bond formation followed by cyclization via C[sbnd]N bond formation to afford the 2,3-disubstituted indoles, involving an unexpected aryl group migration. In this methodology, anilines act as bis-nucleophiles, wherein the initial attack occurs at the α-position of enol ether from the ortho position of aniline followed by the subsequent reaction of the amine moiety of aniline at the β-position, leading to the indole framework. This method is simple, obviates the use of expensive/hazardous transition-metal catalysts, and offers a wide range of substrate scope.

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IITH Creators:
IITH CreatorsORCiD
Jena, Tapan KumarUNSPECIFIED
Khan, Faiz AhmedUNSPECIFIED
Item Type: Article
Uncontrolled Keywords: Article; catalyst; chemical interaction; chemical structure; column chromatography; environmental temperature; nucleophilicity; phase transition; reaction optimization; solvent effect; substitution reaction; synthesis; tautomerization
Subjects: Chemistry
Divisions: Department of Chemistry
Depositing User: . LibTrainee 2021
Date Deposited: 19 Jul 2021 06:09
Last Modified: 19 Jul 2021 06:09
URI: http://raiith.iith.ac.in/id/eprint/8421
Publisher URL: http://doi.org/10.1016/j.tetlet.2020.152583
OA policy: https://v2.sherpa.ac.uk/id/publication/15870
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