5-(1h-indol-1-yl)-dihydrofuran-2-(3h)-ones and methods for their synthesis

CN118388460BActive Publication Date: 2026-06-19SOUTH CHINA UNIV OF TECH
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Patent Information

Application Number
CN202410493067.7
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-04-23
Publication Date
2026-06-19
Estimated Expiration
2044-04-23

AI Technical Summary

Technical Problem

但在已有的报道中，大多通过导向基如8-氨基喹啉等保护3-丁烯酸的羧基，只利用3-丁烯酸的碳碳双键参与反应，活性官能团的利用率并不高(Nimmagadda,S.K.；Liu,M.；Karunananda,M.K.；Gao,D.W.；Apolinar,O.；Chen,J.S.；Liu,P.；Engle,K.M.Angew.Chem.,Int.Ed.,2019,58,3923.；Wang,C.；Xiao,G.；Guo,T.；Ding,Y.；Wu,X.；Loh,T.P.J.Am.Chem.Soc.,2018,140,9332.；Wang,H.；Bai,Z.；Jiao,T.；Deng,Z.；Tong,H.；He,G.；Peng,Q.；Chen,G.P.J.Am.Chem.Soc.,2018,140,3542-3546.；Lv,H.；Xiao,L.；Zhao,D.；Zhou,Q.；Chem.Sci.,2018,9,6839.；Shen,H.；Zhang,L.；Chen,S.；Feng,J.；Zhang,B.；Zhang,Y.；Zhang,X.；Wu,Y.；Gong,L.ACS Catal.,2018,9,791.；Wei,C.；Ye,X.；Xing,Q.；Hu,Y.；Xie,Y.；Shi,X.Org.Biomol.Chem.,2019,17,6607.)

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Abstract

This invention discloses a 5-(1H-indol-1-yl)-dihydrofuran-2-(3H)-one compound and its synthetic method. The synthetic method involves reacting 2-ethynylaniline and 3-butenoic acid in an organic solvent under an air atmosphere with a palladium catalyst, ligand, oxidant, and additives to obtain the 5-(1H-indol-1-yl)-dihydrofuran-2-(3H)-one compound. This invention constructs a series of highly functionalized 5-(1H-indol-1-yl)-dihydrofuran-2-(3H)-one compounds, exhibiting extremely high step economy and atom economy. Furthermore, the method is characterized by readily available and simple starting materials, safe operation, good regioselectivity, and broad substrate universality.
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