Premium
N ‐Bromosuccinimide‐Mediated Thiocyanation of Cyclohexene‐Fused Isoxazoline N ‐Oxides
Author(s) -
Ichake Sachin S.,
Rajawinslin R. R.,
Kavala Veerababurao,
Villuri Bharath Kumar,
Yang HueiTing,
Kuo ChunWei,
Yao ChingFa
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500453
Subject(s) - chemistry , isothiazole , cyclohexanone , n bromosuccinimide , cyclohexene , acetonitrile , ring (chemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , halogenation , catalysis
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.