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

Anikó Angyal; András Demjén; Veronika Harmat; János Wölfling; László G Puskás; Iván Kanizsai

doi:10.1021/acs.joc.9b00242

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

J Org Chem. 2019 Apr 5;84(7):4273-4281. doi: 10.1021/acs.joc.9b00242. Epub 2019 Mar 19.

Authors

Anikó Angyal^{1

2}, András Demjén¹, Veronika Harmat³, János Wölfling², László G Puskás¹, Iván Kanizsai¹

Affiliations

¹ AVIDIN Ltd. , Alsó kikötő sor 11/D, Szeged H-6726 , Hungary.
² Department of Organic Chemistry , University of Szeged , Dóm tér 8, H-6720 Szeged , Hungary.
³ Laboratory of Structural Chemistry and Biology, and MTA-ELTE Protein Modeling Research Group , Institute of Chemistry, Eötvös Loránd University , Pázmány P. sétány 1/A, H-1117 Budapest , Hungary.

PMID: 30860375
DOI: 10.1021/acs.joc.9b00242

Abstract

A regio- and diastereoselective 1,3-dipolar cycloaddition of 2 H-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.

Publication types

Research Support, Non-U.S. Gov't