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^*

^*Corresponding author for this work

Department of Chemistry

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

9 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

Keywords

Cyclohexenes
Heterocycles
Isoxazoline N-oxides
N-bromosuccinimide
Thiocyanation

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1002/ajoc.201500453

Cite this

@article{89da414eeecf4061a4e9e003a50c3665,

title = "N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides",

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.",

keywords = "Cyclohexenes, Heterocycles, Isoxazoline N-oxides, N-bromosuccinimide, Thiocyanation",

author = "Ichake, {Sachin S.} and Rajawinslin, {R. R.} and Veerababurao Kavala and Villuri, {Bharath Kumar} and Yang, {Huei Ting} and Kuo, {Chun Wei} and Yao, {Ching Fa}",

note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

month = mar,

day = "1",

doi = "10.1002/ajoc.201500453",

language = "English",

volume = "5",

pages = "343--352",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "John Wiley and Sons Inc.",

number = "3",

}

TY - JOUR

T1 - N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides

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

PY - 2016/3/1

Y1 - 2016/3/1

N2 - 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.

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.

KW - Cyclohexenes

KW - Heterocycles

KW - Isoxazoline N-oxides

KW - N-bromosuccinimide

KW - Thiocyanation

UR - http://www.scopus.com/inward/record.url?scp=84961157249&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84961157249&partnerID=8YFLogxK

U2 - 10.1002/ajoc.201500453

DO - 10.1002/ajoc.201500453

M3 - Article

AN - SCOPUS:84961157249

SN - 2193-5807

VL - 5

SP - 343

EP - 352

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 3

ER -

N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 1412254: Experimental Crystal Structure Determination

CCDC 1412886: Experimental Crystal Structure Determination

CCDC 1412637: Experimental Crystal Structure Determination

Cite this

N-Bromosuccinimide-Mediated Thiocyanation of Cyclohexene-Fused Isoxazoline N-Oxides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 1412254: Experimental Crystal Structure Determination

CCDC 1412886: Experimental Crystal Structure Determination

CCDC 1412637: Experimental Crystal Structure Determination

Cite this