1,4-二取代丁-3-炔-1-酮的5-内-亲电环化反应：2,5-二取代3-溴呋喃和3-碘呋喃的区域选择性合成
5-Endo-dig electrophilic cyclization of 1,4-disubstituted but-3-yn-1-ones: regiocontrolled synthesis of 2,5-disubstituted 3-bromo- and 3-iodofurans.
作者信息
Sniady Adam, Wheeler Kraig A, Dembinski Roman
机构信息
Department of Chemistry, Oakland University, 2200 North Squirrel Road, Rochester, Michigan 48309-4477, USA.
出版信息
Org Lett. 2005 Apr 28;7(9):1769-72. doi: 10.1021/ol050372i.
PMID:15844902
Abstract
[reaction: see text] 5-Endo-dig electrophilic cyclization of 1,4-diaryl but-3-yn-1-ones with N-bromosuccinimide or N-iodosuccinimide/acetone and iodine monochloride/CH(2)Cl(2), at room temperature, in the absence of base, provides 3-halo-2,5-diarylfurans with excellent regiocontrol and high yields (81-94%).
摘要
[反应：见正文] 在室温下，于无碱条件下，1,4 - 二芳基 - 3 - 丁炔 - 1 - 酮与N - 溴代琥珀酰亚胺或N - 碘代琥珀酰亚胺/丙酮以及一氯化碘/二氯甲烷发生5 - 内型 - 亲电环化反应，可提供具有出色区域选择性控制和高收率（81 - 94%）的3 - 卤代 - 2,5 - 二芳基呋喃。
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