Journal
ORGANIC LETTERS
Volume 12, Issue 12, Pages 2884-2887Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol101040p
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Funding
- National Institutes of Health NIGMS [R01GM084945]
- University of Illinois at Chicago
- Petroleum Research Fund
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Iron(II) bromide catalyzes the transformation of aryl and vinyl azides with ketone or methyl oxime substituents Into 2,1-benzisoxazoles, indazoles, or pyrazoles through the formation of an N-O or N-N bond. This transformation tolerates a variety of different functional groups to facilitate access to a range of benzisoxazoles or indazoles. The unreactivity of the Z-methyloxime indicates that N-heterocycle formation occurs through a nucleophilic attack of the ketone or oxime onto an activated planar iron azide complex.
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