Regioselective synthesis of 1, 5-diarylpyrazole derivatives from hex-1-en-3-uloses. (19th November 2022)

• Record Type: Journal Article
• Authors: Chen, Po-Yen; Huang, Wei-Tsung; Hsieh, Min-Tsang; Chang, Chih-Shiang; Lin, Hui-Chang
• Is Part Of: Tetrahedron. Volume 127(2022)
• Publication Date: 2022-11-19
• Subjects: Heck reaction -- 1, 5-Diarylpyrazole -- C-Glycosylation -- Hex-1-en-3-uloses -- Microwave; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.133070
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: 1, 5-diarylpyrazoles were synthesized by a two-step procedure starting from hex-1-en-3-uloses. The initial microwave-assisted oxidative Heck type C-glycosylation of hex-1-en-3-uloses with arylboronic acids in the presence of Pd(OAc)2 and DDQ afforded C -1 aryl enones. The resulting product further reacted with arylhydrazines in the presence of InCl3 and oxygen to give the 1, 5-diarylpyrazoles in moderate to good yields (51–83%). Graphical abstract: Image 1