One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source
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一锅铜催化级联双环化策略合成 2-(1H-吲哚-1-基)-4,5-二氢噻唑和 2-(1H-吲哚-1-基)噻唑-5-基芳基酮
DOI：
10.1002/adsc.201801193
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发表时间：
2019
影响因子：
5.4
通讯作者：
Wang Qingmin
中科院分区：
文献类型：
--
作者：
Xie Jialin;Guo Zhonglin;Huang Yuanqiong;Qu Yi;Song Hongjian;Song Haibin;Liu Yuxiu;Wang Qingmin
本文报道了一种从邻炔基苯基异硫氰酸酯和炔丙胺衍生物合成N-杂环吲哚的原子经济方法。该方法涉及由分子内5-外-二氢硫醇化反应和分子内氢胺化反应组成的铜催化级联双环化过程，并且取决于分子氧是否存在，以令人满意的产率选择性地提供2-（1H-吲哚-1-基）-4，5-二氢噻唑或2-（1H-吲哚-1-基）噻唑-5-基芳基酮的Z-异构体。机理研究表明，分子氧作为氧源的酮部分的产品。
An atom‐economical method for synthesizingN‐heterocyclic indoles from readily availableo‐alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper‐catalyzed cascade bicyclization process consisting of an intramolecular 5‐exo‐dighydrothiolation reaction and an intramolecular hydroamination reaction and, depending on whether or not molecular oxygen is present, selectively affordsZ‐isomers of 2‐(1H‐indol‐1‐yl)‐4,5‐dihydrothiazoles or 2‐(1H‐indol‐1‐yl)thiazol‐5‐yl aryl ketones in satisfactory yields. Mechanistic studies indicate that molecular oxygen acts as the oxygen source for the ketone moiety in the products.