Sc(OTf)3‐Catalyzed Tunable Thio‐(3+3) Annulation Reactions of Indoline‐2‐thiones with α‐Benzylidene‐β‐tetralones

IF 2.8 4区化学 Q1 CHEMISTRY, ORGANIC

Asian Journal of Organic Chemistry Pub Date : 2025-02-01 DOI:10.1002/ajoc.202400452

Yan Jiang , Hao‐Jie Ma , Chen‐Ying Zhai , Xue‐Long Wang , Yi Yang

引用次数: 0

Abstract

A Sc(OTf)₃‐catalyzed tunable thio‐Michael addition/nucleophilic addition/dehydration reaction of indoline‐2‐thiones with α‐benzylidene‐β‐tetralones was realized, leading to biologically important tetrahydrobenzo[7,8]isothiochromeno[3,4‐b]indoles and thiazino[3,2‐a]indoles in moderate to good yields. Moreover, by extending the reaction time, the dehydrogenated cycloadducts dihydrobenzo[7,8]isothiochromeno[3,4‐b]indoles were also obtained from the reaction of indoline‐2‐thiones with α‐benzylidene‐β‐tetralones.

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在 Sc(OTf)3 催化下，实现了吲哚啉-2-硫酮与α-亚苄基-β-四氢萘酮的可调硫代-迈克尔加成/亲核加成/脱水反应，从而以中等至良好的收率制备出具有重要生物学意义的四氢苯并[7,8]异硫代苯并[3,4-b]吲哚和噻嗪并[3,2-a]吲哚。此外，通过延长反应时间，还可以从吲哚啉-2-硫酮与α-亚苄基-β-四氢萘酮的反应中获得脱氢环加载产物二氢苯并[7,8]异硫代苯并[3,4-b]吲哚。

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来源期刊

Asian Journal of Organic Chemistry CHEMISTRY, ORGANIC-

CiteScore

4.70

自引率

3.70%

发文量

372

期刊介绍： Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.