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1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2<i>H</i>‑Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles

By Anikó Angyal (4925659), András Demjén (4925656), Veronika Harmat (24766), János Wölfling (2384725), László G. Puskás (4925662) and Iván Kanizsai (4925650)


A regio- and diastereoselective 1,3-dipolar cycloaddition of 2<i>H</i>-azirines with azomethine ylides generated in situ from isatins and α-amino acids has been elaborated, affording an unprecedented aziridine-fused spiro­[imidazolidine-4,3′-oxindole] framework. This one-pot three-component reaction tolerates a wide range of substrates and enables the construction of highly diverse 1,3-diazaspiro­[bicyclo[3.1.0]­hexane]­oxindoles in isolated yields up to 81% under mild conditions

Topics: Biochemistry, Medicine, Microbiology, Molecular Biology, Ecology, Sociology, Plant Biology, Space Science, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, diastereoselective, aziridine-fused, one-pot three-component reaction, azirine, Stereoselective Synthesis, Isatin-Derived Azomethine Ylides, Dipolar, acid, cycloaddition, spiro, azomethine ylides, Diazaspiro, dipolar, construction, diazaspiro, regio, substrate, framework, yield, Azirine, isatin, 2 H, α-, Cycloaddition
Year: 2019
DOI identifier: 10.1021/acs.joc.9b00242.s003
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Provided by: FigShare
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