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^*

^*Corresponding author for this work

Department of Chemistry

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

6 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

Access to Document

10.1016/j.tet.2014.08.024

Cite this

@article{b59c84e8b0d6440f9e56027732b18fe2,

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",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "41",

}

TY - JOUR

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 955136: Experimental Crystal Structure Determination

CCDC 989222: Experimental Crystal Structure Determination

Cite this

Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 955136: Experimental Crystal Structure Determination

CCDC 989222: Experimental Crystal Structure Determination

Cite this