Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3-b]indole-3(5H)-thiones,The Journal of Organic Chemistry

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Lithium-Promoted Cycloaddition of Indole-2,3-dienolates and Carbon Disulfide as a One-Pot Route to Thiopyrano[4,3-b]indole-3(5H)-thiones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2021-08-02 , DOI: 10.1021/acs.joc.1c01200
Konstantin F Suzdalev ₁ , Julia V Vyalyh ₁ , Valery V Tkachev ₂ , Ekaterina A Lysenko ₁ , Oleg N Burov ₁ , Anton V Lisovin ₁ , Mikhail E Kletskii ₁ , Sergey V Kurbatov ₁

Affiliation

A new approach for the annulation of a thiopyrane ring to an indole core under mild conditions was developed. Treating 2-methyl-3-acylindoles with lithium diisopropyl amide leads to the elimination of a proton from the 2-methyl group. The lithium indole-2,3-dienolates obtained were found to react with CS₂ to give the corresponding thiopyrano[4,3-b]indole-3(5H)-thiones. The mechanism represents a stepwise addition through ion-pair formation, according to PCM/B3LYP/6-311++G**, PBE1PBE/6-311++G**, and MP2//HF/6-311++G** quantum chemical calculations. AIM calculations revealed the essential role of the Li atom at all stages of the process.

中文翻译：

锂促进 Indole-2,3-dienolates 和二硫化碳的环加成作为一锅法合成噻吩并 [4,3-b]indole-3(5H)-thiones

开发了一种在温和条件下将噻喃环与吲哚核成环的新方法。用二异丙基氨基锂处理 2-甲基-3-酰基吲哚导致从 2-甲基基团消除一个质子。发现获得的吲哚-2,3-二烯醇锂与CS ₂反应得到相应的噻喃并[4,3 - b ]吲哚-3(5 H )-硫酮。根据 PCM/B3LYP/6-311++G**、PBE1PBE/6-311++G** 和 MP2//HF/6-311++G，该机制代表通过离子对形成的逐步加成** 量子化学计算。AIM 计算揭示了锂原子在该过程的所有阶段的重要作用。

更新日期：2021-09-03

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