Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 5, Issue 3, Pages 343-352Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.201500453
Keywords
cyclohexenes; heterocycles; isoxazoline N-oxides; N-bromosuccinimide; thiocyanation
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Funding
- Ministry of Science and Technology of the Republic of China [MOST 103-2113M-003-008-MY3]
- National Taiwan Normal University [103-07-C]
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An efficient, metal-free, NBS-mediated thiocyanation protocol has been developed for the synthesis of (6-(hydroxyimino)-2-thiocyanatocyclohex-1-en-1-yl)(phenyl)methanone derivatives from cyclohexene-fused isoxazoline N-oxides under mild conditions. This rapid, one-pot transformation is achieved in acetonitrile, and provides access to diverse SCN-containing compounds bearing a wide range of functional groups in good to excellent yields. Moreover, an SCN containing product was further utilized for the synthesis of cyclohexanone ring-fused isothiazole derivatives.
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