Easy Access to 2-Fluoro- and 2-Iodo-2H-azirines via the Halex Reaction

Abstract A simple gram-scale method for the preparation of esters and dialkylamides of 2-(fluoro/iodo)-2 H -azirine-2-carboxylic acids via the halogen exchange (Halex) reaction of 2-bromo-substituted analogues is reported. The method operates with inexpensive and safe reagents­, Bu 4 NF and potassiu...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2019-12, Vol.51 (24), p.4582-4589
Main Authors: Agafonova, Anastasiya V., Smetanin, Ilia A., Rostovskii, Nikolai V., Khlebnikov, Alexander F., Novikov, Mikhail S.
Format: Article
Language:English
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Summary:Abstract A simple gram-scale method for the preparation of esters and dialkylamides of 2-(fluoro/iodo)-2 H -azirine-2-carboxylic acids via the halogen exchange (Halex) reaction of 2-bromo-substituted analogues is reported. The method operates with inexpensive and safe reagents­, Bu 4 NF and potassium iodide, providing high product yields. Alternatively, 2-fluoro-2 H -azirine-2-carboxylates can be prepared from 2-iodo- and 2-chloro-analogues. The latter compounds can be obtained in practically quantitative yield by treating the 2-iodo- and 2-bromo-2 H -azirine-2-carboxylic esters with Bu 4 NCl.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0039-1690200