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, V. Harmat, J. Wölfling, L. Puskás, Iván Kanizsai

Research output: Article

1 Citation (Scopus)

Abstract

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

Original languageEnglish
Pages (from-to)4273-4281
Number of pages9
JournalJournal of Organic Chemistry
Volume84
Issue number7
DOIs
Publication statusPublished - ápr. 5 2019

Fingerprint

Azirines
Isatin
Cycloaddition
Imidazolidines
Amino Acids
Substrates
bicyclo(3.1.0)hexane
azomethine
oxindole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "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",
abstract = "A regio- A nd diastereoselective 1,3-dipolar cycloaddition of 2H-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.",
author = "Anik{\'o} Angyal and Andr{\'a}s Demj{\'e}n and V. Harmat and J. W{\"o}lfling and L. Pusk{\'a}s and Iv{\'a}n Kanizsai",
year = "2019",
month = "4",
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journal = "Journal of Organic Chemistry",
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publisher = "American Chemical Society",
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TY - JOUR

T1 - 1,3-dipolar cycloaddition of Isatin-derived azomethine ylides with 2 H-azirines

T2 - Stereoselective synthesis of 1,3-diazaspiro[bicyclo[3.1.0]hexane]oxindoles

AU - Angyal, Anikó

AU - Demjén, András

AU - Harmat, V.

AU - Wölfling, J.

AU - Puskás, L.

AU - Kanizsai, Iván

PY - 2019/4/5

Y1 - 2019/4/5

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

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