偕二卤亚甲基-3-氧代酮肟衍生物的卤化鎓离子介导合成：异恶唑啉 N-氧化物。
Halonium ion mediated synthesis of 2-halomethylene-3-oxoketoxime derivatives from isoxazoline N-oxides.
机构信息
Department of Chemistry, National Taiwan Normal University, 88, Sec. 4, Tingchow Road, Taipei116, Taiwan, R.O.C.
出版信息
J Org Chem. 2013 Sep 6;78(17):8872-9. doi: 10.1021/jo401283x. Epub 2013 Aug 27.
A protocol for the N-bromosuccinimide (NBS)- and trichloroisocyanuric acid (TCCA)-mediated synthesis of novel 2-halomethylene-3-oxoketoximes via one-pot halogenation/oxidation of isoxazoline N-oxide derivatives is described here. The keto functionality of 3-ketoximes was selectively reduced by lithiumaluminum hydride to synthesize an unprecedented type of Baylis-Hillman oxime, which underwent N-O coupling to produce new isoxazoline N-oxide derivative.
本文描述了通过异噁唑啉 N-氧化物衍生物的一锅卤化/氧化反应，用 N-溴代琥珀酰亚胺（NBS）和三氯异氰尿酸（TCCA）合成新型 2-卤亚甲基-3-氧代酮肟的方法。通过氢化锂铝选择性还原 3-酮肟的酮官能团，合成了一种前所未有的 Baylis-Hillman 肟，该肟发生 N-O 偶联生成新的异噁唑啉 N-氧化物衍生物。
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