通过涉及 C-C 键裂解的间断海因斯重排，区域选择性合成 2,3 二甲基吲哚。

IF 3.5 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemistry - An Asian Journal Pub Date : 2024-11-04 Epub Date: 2024-10-03 DOI:10.1002/asia.202400731

Minakshi Altia, Pazhamalai Anbarasan

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引用次数: 0

摘要

我们开发了一种新型的无金属、以布氏酸为介导且操作简单的策略，用于以α-羟基酮和邻氨基芳基酮为原料，区域选择性合成 2,3-二取代吲哚，收率极高。该反应通过间断的 Heyns 重排，生成氨基烯醇中间体，然后进行分子内捕获和芳香化，C-C 键断裂并释放出相应的酯。通过 GCMS 鉴定出酯，并与环状 α-羟基二甲基缩酮反应，得到了酯系吲哚衍生物，从而进一步证实了该机理。

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Regioselective Synthesis of 2,3-Disubstituted Indoles via Interrupted Heyns Rearrangement Involving C-C Bond Cleavage.

A novel metal free, Brønsted acid mediated and operationally simple strategy has been developed for regioselective synthesis of 2,3-disubstituted indoles from α-hydroxyketones and o-aminoaryl ketones in excellent yields. The reaction proceeds via interrupted Heyns rearrangement through the generation of aminoenol intermediate followed by intramolecular trapping and aromatization with C-C bond cleavage and release of corresponding ester. The mechanism was further supported by the identification of ester in GCMS and reaction of cyclic α-hydroxydimethylketal, which afforded ester tethered indole derivative.

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来源期刊

Chemistry - An Asian Journal 化学-化学综合

CiteScore

7.00

自引率

2.40%

发文量

535

审稿时长

1.3 months

期刊介绍： Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).