Journal
TETRAHEDRON
Volume 68, Issue 47, Pages 9836-9841Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.08.076
Keywords
N-Heterocyclic carbene; Sequential one-pot reaction; Three-component reaction; Umpolung; Deoxy-Breslow intermediate
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Funding
- Grants-in-Aid for Scientific Research [24750102] Funding Source: KAKEN
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The tandem sequence of the umpolung of alpha,beta-unsaturated esters by an N-heterocyclic carbene (NHC) followed by annulation is demonstrated. The deoxy-Breslow intermediates are selectively generated from the reaction of NHC with methyl methacrylate, dimethyl itaconate, or methyl crotonate. Subsequently, they undergo annulation with isocyanates to give 4-(1,2,4-triazol-5-ylidene)pyrrolidine-2,5-diones in good isolated yields. In addition, the stoichiometric three-component reaction of NHC, methyl methacrylate, and phenyl isocyanate proceeded, accompanied by the formation of the 1:2 adduct of NHC with phenyl isocyanate. (c) 2012 Elsevier Ltd. All rights reserved.
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