Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives

R. R. Rajawinslin, Mustafa J. Raihan, Donala Janreddy, Veerababurao Kavala, Chun Wei Kuo, Ting Shen Kuo, Mei Ling Chen, Chiu Hui He, Ching Fa Yao

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A Selectfluor and base mediated protocol for the synthesis of cyclohexanone ring fused isoxazole derivatives from isoxazoline N-oxides has been successfully developed. This rapid, one-pot, two-step transformation is achieved in acetonitrile, through nitroso intermediate followed by hydration, defluorination and N-O coupling in the presence of triethylamine. The scope and mechanism of the protocol have been demonstrated.

Original languageEnglish
Pages (from-to)7505-7510
Number of pages6
JournalTetrahedron
Volume70
Issue number41
DOIs
Publication statusPublished - 2014 Oct 14

Fingerprint

Isoxazoles
Hydration
Oxides
Derivatives
cyclohexanone
triethylamine
acetonitrile
selectfluor

Keywords

  • Defluorination
  • Heterocycles
  • N-O coupling
  • Synthetic methods

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Rajawinslin, R. R., Raihan, M. J., Janreddy, D., Kavala, V., Kuo, C. W., Kuo, T. S., ... Yao, C. F. (2014). Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives. Tetrahedron, 70(41), 7505-7510. https://doi.org/10.1016/j.tet.2014.08.024

Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives. / Rajawinslin, R. R.; Raihan, Mustafa J.; Janreddy, Donala; Kavala, Veerababurao; Kuo, Chun Wei; Kuo, Ting Shen; Chen, Mei Ling; He, Chiu Hui; Yao, Ching Fa.

In: Tetrahedron, Vol. 70, No. 41, 14.10.2014, p. 7505-7510.

Research output: Contribution to journalArticle

Rajawinslin, RR, Raihan, MJ, Janreddy, D, Kavala, V, Kuo, CW, Kuo, TS, Chen, ML, He, CH & Yao, CF 2014, 'Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives', Tetrahedron, vol. 70, no. 41, pp. 7505-7510. https://doi.org/10.1016/j.tet.2014.08.024
Rajawinslin RR, Raihan MJ, Janreddy D, Kavala V, Kuo CW, Kuo TS et al. Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives. Tetrahedron. 2014 Oct 14;70(41):7505-7510. https://doi.org/10.1016/j.tet.2014.08.024
Rajawinslin, R. R. ; Raihan, Mustafa J. ; Janreddy, Donala ; Kavala, Veerababurao ; Kuo, Chun Wei ; Kuo, Ting Shen ; Chen, Mei Ling ; He, Chiu Hui ; Yao, Ching Fa. / Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives. In: Tetrahedron. 2014 ; Vol. 70, No. 41. pp. 7505-7510.
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