Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 343-352 |
| Number of pages | 10 |
| Journal | Asian Journal of Organic Chemistry |
| Volume | 5 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - 2016 Mar 1 |
Keywords
- Cyclohexenes
- Heterocycles
- Isoxazoline N-oxides
- N-bromosuccinimide
- Thiocyanation
ASJC Scopus subject areas
- Organic Chemistry
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Cite this
Ichake, S. S., Rajawinslin, R. R., Kavala, V., Villuri, B. K., Yang, H. T., Kuo, C. W., & Yao, C-F. (2016). N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides. Asian Journal of Organic Chemistry, 5(3), 343-352. https://doi.org/10.1002/ajoc.201500453