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

doi:10.1002/ajoc.201500453

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

Department of Chemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	343-352
Number of pages	10
Journal	Asian Journal of Organic Chemistry
Volume	5
Issue number	3
DOIs	https://doi.org/10.1002/ajoc.201500453
Publication status	Published - 2016 Mar 1

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Keywords

Cyclohexenes
Heterocycles
Isoxazoline N-oxides
N-bromosuccinimide
Thiocyanation

ASJC Scopus subject areas

Organic Chemistry

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

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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.",

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AU - Ichake, Sachin S.

AU - Rajawinslin, R. R.

AU - Kavala, Veerababurao

AU - Villuri, Bharath Kumar

AU - Yang, Huei Ting

AU - Kuo, Chun Wei

AU - Yao, Ching-Fa

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AB - 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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Access to Document

10.1002/ajoc.201500453