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HOAc-Mediated Domino Diels-Alder Reaction for Synthesis of Spiro[cyclohexane-1,3'-indolines] in Ionic Liquid [Bmim]Br.

ABSTRACT: 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.

SUBMITTER: Yang RY

PROVIDER: S-EPMC6641705 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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HOAc-Mediated Domino Diels-Alder Reaction for Synthesis of Spiro[cyclohexane-1,3'-indolines] in Ionic Liquid [Bmim]Br.

Yang Ren-Yin RY Sun Jing J Yan Chao-Guo CG

ACS omega 20180521 5

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-Ald ...[more]

PMID: 31458748

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