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,Advanced Synthesis & Catalysis

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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
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-12-14 , DOI: 10.1002/adsc.201801193
Jialin Xie ₁ , Zhonglin Guo ₁ , Yuanqiong Huang ₁ , Yi Qu ₁ , Hongjian Song ₁ , Haibin Song ₁ , Yuxiu Liu ₁ , Qingmin Wang _{1,

2}

Affiliation

An atom‐economical method for synthesizing N‐heterocyclic indoles from readily available o‐alkynylphenyl isothiocyanates and propargylamine derivatives is reported. This method involves a copper‐catalyzed cascade bicyclization process consisting of an intramolecular 5‐exo‐dig hydrothiolation reaction and an intramolecular hydroamination reaction and, depending on whether or not molecular oxygen is present, selectively affords Z‐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.

中文翻译：

一锅铜催化的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-基芳基酮氧气作为氧气源

据报道，一种原子经济的方法可以从现成的邻炔基苯基异硫氰酸酯和炔丙基胺衍生物合成N杂环吲哚。该方法包括由分子内的5-铜催化级联bicyclization过程外切挖hydrothiolation反应和分子内加氢胺化反应，并且根据分子氧是否存在时，选择性地得到ž -异构体的2-（1 ħ -吲哚-1-基）-4,5-二氢噻唑或2-（1 H-吲哚-1-基）噻唑-5-基芳基酮，收率令人满意。机理研究表明，分子氧充当产物中酮部分的氧源。

更新日期：2018-12-14

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