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^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

6 引文斯高帕斯（Scopus）

摘要

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.

原文	英語
頁（從 - 到）	7505-7510
頁數	6
期刊	Tetrahedron
卷	70
發行號	41
DOIs	https://doi.org/10.1016/j.tet.2014.08.024
出版狀態	已發佈 - 2014 10月 14

ASJC Scopus subject areas

生物化學
藥物發現
有機化學

存取文件

10.1016/j.tet.2014.08.024

其它文件與鏈接

CCDC 955136: Experimental Crystal Structure Determination
Rajawinslin, R. R. (Creator), Raihan, M. J. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator), Kuo, T. (Creator), Chen, M. (Creator), He, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc111wvt, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc111wvt&sid=DataCite
資料集: Dataset
CCDC 989222: Experimental Crystal Structure Determination
Rajawinslin, R. R. (Creator), Raihan, M. J. (Creator), Janreddy, D. (Creator), Kavala, V. (Creator), Kuo, C. (Creator), Kuo, T. (Creator), Chen, M. (Creator), He, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2015
DOI: 10.5517/cc126cd1, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc126cd1&sid=DataCite
資料集: Dataset

引用此

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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}",

year = "2014",

month = oct,

day = "14",

doi = "10.1016/j.tet.2014.08.024",

language = "English",

volume = "70",

pages = "7505--7510",

journal = "Tetrahedron",

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T1 - Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives

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

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.

KW - Defluorination

KW - Heterocycles

KW - N-O coupling

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84907074719&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84907074719&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2014.08.024

DO - 10.1016/j.tet.2014.08.024

M3 - Article

AN - SCOPUS:84907074719

SN - 0040-4020

VL - 70

SP - 7505

EP - 7510

JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 955136: Experimental Crystal Structure Determination

CCDC 989222: Experimental Crystal Structure Determination

引用此