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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6641705 | PMC |
| http://dx.doi.org/10.1021/acsomega.8b00464 | DOI Listing |
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HOAc-Mediated Domino Diels-Alder Reaction for Synthesis of Spiro[cyclohexane-1,3'-indolines] in Ionic Liquid [Bmim]Br.
ACS Omega
May 2018
College of Chemistry, Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
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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