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Functional Ionic Liquids Promoted Double Michael Reaction of Benzofuran‐3‐one or 1‐Indone and Symmetric Dienones: Construction of Spiro[benzofuran‐2,1’‐cyclohexane]‐3‐one or Spiro[cyclohexane‐1,2’‐indene]‐1’,4(3’ H )‐dione Derivatives
Author(s) -
Liu Chunhui,
Xu Yalun,
Niu Songyang,
Wei Liquan,
Liu Yong,
Wang Yanbo,
Zhu Junyan,
Fu Jiya,
Yuan Jinfang
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600796
Subject(s) - benzofuran , chemistry , indene , cyclohexane , stereocenter , ionic liquid , catalysis , michael reaction , medicinal chemistry , organic chemistry , enantioselective synthesis
The double Michael reactions between benzofuran‐3‐one or 1‐indone and symmetric dienones in the presence of catalytic ionic liquids were successfully developed and spiro[benzofuran‐2,1’‐cyclohexane]‐3‐one or spiro[cyclohexane‐1,2’‐indene]‐1’,4(3’ H )‐dione derivatives containing a spiro quaternary stereogenic center, which widely exist in biologically active products and building blocks in organic synthesis, were obtained in excellent yields (up to 99%). This catalytic system was also extended to the double Michael reaction of less reactive 1‐indone and the desired products were also obtained in 31%‐62% yields. The catalytic system was highly active and efficient for a broad of substrates under mild conditions.