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
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U2 - 10.1002/ajoc.201500453
DO - 10.1002/ajoc.201500453
M3 - Article
AN - SCOPUS:84961157249
VL - 5
SP - 343
EP - 352
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
SN - 2193-5807
IS - 3
ER -