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Synthesis 2018; 50(10): 2124-2130
DOI: 10.1055/s-0037-1609433
DOI: 10.1055/s-0037-1609433
paper
Preparation of Trifluoromethylated (Arylaminomethylene)malononitriles Suitable for Synthesis of 4-Amino-2-(trifluoromethyl) quinoline Derivatives by Intramolecular Friedel–Crafts Reaction
Authors
We gratefully acknowledge the Vali-e-Asr University of Rafsanjan Faculty Research Grant for financial support.
Further Information
Publication History
Received: 28 December 2017
Accepted after revision: 26 February 2018
Publication Date:
28 March 2018 (online)
Abstract
An approach for the synthesis of 4-amino-2-(trifluoromethyl)quinolines via the intramolecular Friedel–Crafts reaction of 2-(1-(arylamino)-2,2,2-trifluoroethylidene)malononitrile derivatives is reported. This simple protocol provides a wide variety of 4-amino-2-(trifluoromethyl)quinolines in good to excellent yields, without any purification. Furthermore, the 2-(1-(arylamino)-2,2,2-trifluoroethylidene) malononitrile derivatives used in this project have been synthesized by the reaction of N-aryl-2,2,2-trifluoroacetimidoyl chlorides and malononitrile at ambient temperature and under microwave irradiation in excellent yields, for the first time.
Key words
4-amino-2-(trifluoromethyl)quinolones - intramolecular Friedel–Crafts reaction - trifluoromethylated (arylaminomethylene)malononitriles - trifluoroacetimidoyl chlorides - trifluoromethylated compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609433.
- Supporting Information (PDF)
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