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Isoxazoles via Cycloaddition of Terminal Alkynes and Nitrile Oxides (from Oximes)
*
,
,
Rebecca G Brunner
,
Isuru M Jayalath
,
Kate G. E. Bradford
Academic Editor: Julio A. Seijas
Published:
14 November 2021
by MDPI
in The 25th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
https://doi.org/10.3390/ecsoc-25-11778
(registering DOI)
Abstract:
Conditions for the production of isoxazoles in a one-pot process are presented. Nitrile N-oxides are generated by the oxidation (using hypervalent iodine reagents) of oximes that subsequently undergo 1,3-dipolar cycloaddition with terminal alkynes affording the isoxazoles. From a collection of three terminal alkynes and four aldehydic oximes, 11 distinct isoxazoles were prepared. The effectiveness of various oxidants and solvent systems is discussed, as are side reactions.
Keywords: 1,3-dipolar cycloaddition; isoxazoles; hypervalent iodine
