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Synthesis of α‐Amidoacrylates Containing a 3‐Ylideneoxindole Motif
Author(s) -
Song Shuai,
Li Ya,
Chen DeYin,
Wang XiaoPing,
Liu YongLiang,
Chen LingYan
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202100578
Subject(s) - propargyl , chemistry , aryl , alkyl , motif (music) , combinatorial chemistry , stereochemistry , cascade , medicinal chemistry , organic chemistry , catalysis , physics , acoustics , chromatography
Both the α‐amidoacrylate and 3‐ylideneooxindole frameworks are important in medicinal chemistry because of their associated biological activities. We report a novel approach to accessing α‐amidoacrylates containing a 3‐ylideneoxindole motif through a novel cascade process involving condensation between 3‐fluorooxindoles and α‐iminoacetates followed by elimination of HF. This protocol has a broad substrate scope: N ‐alkyl‐, N ‐aryl‐, N ‐allyl‐, N ‐propargyl 3‐fluorooxindoles and 3‐fluorooxindoles with different substituents on the aromatic rings were all suitable for this reaction. A plausible reaction pathway is also presented.