Synthesis of 3-substituted 2-trifluomethyl imidazo[1,2-a]pyridine through [3+2] cycloaddition of pyridinium ylide with trifluoroacetonitrile

[Display omitted] •A general method for synthesis of 2-trifluomethyl imidazo[1,2-a]pyridines was developed.•The use of 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as convenient precursor of trifluoroacetonitrile.•A variety of functional groups were tolerated. A general approach to prepare 2-trifluorom...

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Bibliographic Details
Published inTetrahedron letters Vol. 111; p. 154206
Main Authors Hong, Biqiong, Lin, Bo, Yao, Yunfei, Li, Sailan, Weng, Zhiqiang
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 23.11.2022
Subjects
2-a]pyridines
Cycloaddition
Imidazo
Synthetic methods
Trifluomethylation
Trifluoroacetonitrile
Cycloaddition
Imidazo
Synthetic methods
Trifluoroacetonitrile
2-a]pyridines
Trifluomethylation
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Summary:[Display omitted] •A general method for synthesis of 2-trifluomethyl imidazo[1,2-a]pyridines was developed.•The use of 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as convenient precursor of trifluoroacetonitrile.•A variety of functional groups were tolerated. A general approach to prepare 2-trifluoromethyl imidazo[1,2-a]pyridines by a [3+2] cycloaddition of pyridinium ylide with trifluoroacetonitrile is described. By using 2,2,2-trifluoroacetaldehyde O-(aryl)oxime as convenient precursor of trifluoroacetonitrile, the reaction exhibits a broad substrate scope of pyridinium ylides. The process is a scalable method for the synthesis of potentially bioactive class of 2-trifluoromethyl imidazo[1,2-a]pyridines.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154206