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

doi:10.1016/j.tet.2014.08.024

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 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 language	English
Pages (from-to)	7505-7510
Number of pages	6
Journal	Tetrahedron
Volume	70
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2014.08.024
Publication status	Published - 2014 Oct 14

Keywords

Defluorination
Heterocycles
N-O coupling
Synthetic methods

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.08.024

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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 journal › Article › peer-review

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title = "Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives",

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.",

keywords = "Defluorination, Heterocycles, N-O coupling, Synthetic methods",

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

note = "Funding Information: Financial support for this work by the National Science Council of the Republic of China ( NSC 99-2119-M-003-003-MY3 ) and National Taiwan Normal University ( 99T3030-2 , 99-D , 100-D-06 ) and spectral data collected by the instrumentation center of National Taiwan Normal University is gratefully acknowledged. ",

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AU - Rajawinslin, R. R.

AU - Raihan, Mustafa J.

AU - Janreddy, Donala

AU - Kavala, Veerababurao

AU - Kuo, Chun Wei

AU - Kuo, Ting Shen

AU - Chen, Mei Ling

AU - He, Chiu Hui

AU - Yao, Ching Fa

N1 - Funding Information: Financial support for this work by the National Science Council of the Republic of China ( NSC 99-2119-M-003-003-MY3 ) and National Taiwan Normal University ( 99T3030-2 , 99-D , 100-D-06 ) and spectral data collected by the instrumentation center of National Taiwan Normal University is gratefully acknowledged.

PY - 2014/10/14

Y1 - 2014/10/14

N2 - 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.

AB - 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.

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