Journal
ORGANIC LETTERS
Volume 21, Issue 11, Pages 4219-4223Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01395
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Funding
- Ministry of Science and Technology of the Republic of China [MOST 107-2628-M-003-001-MY3]
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alpha-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of alpha-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.
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