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Preparation of Thioanisole Biscarbanion and C–H Lithiation/Annulation Reactions for the Access of Five-Membered Heterocycles
Organic Letters ( IF 5.2 ) Pub Date : 2018-05-23 00:00:00 , DOI: 10.1021/acs.orglett.8b00850
Ranran Zhu 1, 2, 3 , Zheyuan Liu 2, 4 , Jie Chen 1, 2, 3 , Xiaoyu Xiong 1, 2, 3 , Yuntao Wang 1, 2, 3 , Lin Huang 1, 2, 3 , Jinshan Bai 1, 2, 3 , Yanfeng Dang 2, 4 , Jianhui Huang 1, 2, 3
Affiliation  

The synthesis, isolation, and X-ray structure of a thioanisole-based trilithium complex are reported. On the basis of the double-lithiation strategy, two novel synthetic methodologies have been developed under mild reaction conditions (room temperature): (1) reactions of lithiated thioanisoles with nitriles give benzoisothiazoles via a [3 + 2]-type of approach with two new bond formations and (2) formation of benzothiophenes from thioanisoles and amides through a [4 + 1] pattern forming 4 new chemical bonds.

中文翻译:

硫代苯甲醚双骨架化合物的制备和CH锂化/环化反应,可用于五元杂环

报道了基于硫代苯甲醚的三锂配合物的合成,分离和X射线结构。在双重锂化策略的基础上,在温和的反应条件(室温)下开发了两种新颖的合成方法:(1)锂硫代苯甲醚与腈的反应通过[3 + 2]型方法得到苯并异噻唑,其中两种新的键形成和(2)通过[4 +1]模式由硫代苯甲醚和酰胺形成苯并噻吩,形成4个新的化学键。
更新日期:2018-05-23
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