Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines

Frances H. Bayliffe; Alan Steven; Kaori Ando; Michael Shipman

doi:10.1055/s-0034-1380521

Synlett, Inhaltsverzeichnis

Synlett 2015; 26(10): 1371-1374
DOI: 10.1055/s-0034-1380521

letter

Sodium Amide Induced Cyclization of 2-Iodoprop-2-enylamines: Application to the Synthesis of 1-Aryl-2-methyleneaziridines

Frances H. Bayliffe

^aDepartment of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK eMail: m.shipman@warwick.ac.uk

,

Alan Steven

^bAstraZeneca Pharmaceutical Development, Charter Way, Macclesfield SK10 2NA, Cheshire, UK

,

Kaori Ando

^cDepartment of Chemistry, Faculty of Engineering, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan

,

Michael Shipman*

^aDepartment of Chemistry, University of Warwick, Gibbet Hill Road, Coventry, CV4 7AL, UK eMail: m.shipman@warwick.ac.uk

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Abstract

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Abstract

The effect of the halogen on the rate of sodium amide induced cyclization of 2-haloprop-2-enylamines to methyleneaziridines is studied. Using DFT calculations and competition experiments, it is shown to proceed faster using iodide-based substrates. A practical route to 1-aryl-2-methyleneaziridines is devised based on these observations and their further rearrangement to cyclopropanimines explored.

Key words

aziridines - cyclization - aminocyclopropanes - DFT calculations - vinylic S_N2

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Referenzen

References and Notes

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Zusatzmaterial

Supporting Information