N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides

Sachin S. Ichake, R. R. Rajawinslin, Veerababurao Kavala, Bharath Kumar Villuri, Huei Ting Yang, Chun Wei Kuo, Ching-Fa Yao

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 languageEnglish
Pages (from-to)343-352
Number of pages10
JournalAsian Journal of Organic Chemistry
Volume5
Issue number3
DOIs
Publication statusPublished - 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