Synthesis of difluorinated 3-oxo-N, 3-diarylpropanamides from 4-arylamino coumarins mediated by Selectfluor. Issue 23 (21st October 2021)

• Record Type: Journal Article
• Authors: Chen, Weiqiang; Li, Hui-Jing; Liu, Mei; Gong, Pi-Xian; Wu, Yan-Chao
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 23(2021)
• Page Start: 6636
• Page End: 6641
• Publication Date: 2021-10-21
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01273h
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : An expeditious approach to synthesize difluorinated 3-oxo- N, 3-diarylpropanamides from 4-arylamino coumarins has been accomplished in the presence of Selectfluor, which plays the dual role of a mild oxidant and a source of fluorine. Abstract : An expeditious approach to synthesize difluorinated 3-oxo- N, 3-diarylpropanamides from 4-arylamino coumarins has been accomplished in the presence of Selectfluor, which plays the dual role of a mild oxidant and a source of fluorine. The use of five equivalents of water as an additive plays a key role in this tandem reaction, and the reaction will not occur in the absence of water. The reaction is proposed to involve the difluorination of 4-arylamino coumarins by Selectfluor via a radical process, cleavage of the in situ generated imines, and an amide-formation reaction. The products are confirmed unambiguously from their spectra and by single-crystal X-ray analysis, and are found to exhibit certain hypoglycemic activity.