HOAc-Mediated Domino Diels–Alder Reaction for Synthesis of Spiro[cyclohexane-1,3′-indolines] in Ionic Liquid [Bmim]Br
Author(s) -
RenYin Yang,
Jing Sun,
ChaoGuo Yan
Publication year - 2018
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.8b00464
Subject(s) - cyclohexane , ionic liquid , domino , chemistry , diels–alder reaction , cascade reaction , dehydration , organic chemistry , medicinal chemistry , reaction conditions , catalysis , biochemistry
An efficient and diastereoselective synthetic protocol for the construction of spiro[cyclohexane-1,3'-indolin]-3-en-2'-ones and spiro[cyclohexane-1,2'-inden]-3-ene-1',3'-diones was provided by HOAc-mediated domino reaction of pinacoles with typical dienophiles, such as 3-methyleneoxindolines and 2-arylideneindane-1,3-diones, in ionic liquid [Bmim]Br. This domino reaction involved the in situ generation of 1,3-dienes from acid-mediated dehydration of various pinacoles and the sequential Diels-Alder reaction.
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