Divergent Synthesis of Multisubstituted Hydroindole Derivatives via [3+2] Annulations of p‐Quinamines with Nitroalkenes

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-11-19 DOI:10.1002/adsc.202400647
Hao Qin , Didi Liu , Bingrui Wan , Zhe Liu , Yan Ding , Haonan Zong , Yi Huang , Liang‐Hua Zou , Zengwei Lai
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Abstract

The synthesis of two stereoisomers of hydroindole derivatives was achieved through [3+2] annulations of p‐quinamines with nitroalkenes. Catalyst‐free or in the presence of DMAP, the annulation reactions were employed to produce the target products containing four contiguous stereogenic centers. This method enables the efficient construction of multisubstituted and functionalized hydroindole derivatives from readily accessible building blocks and reagents. Furthermore, the anti‐inflammatory activity of some resulting hydroindoles was evaluated, with three derivative products showing effective inhibition of NLRP3 inflammasome activation.

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通过对喹胺与硝基烯的 [3 + 2] 嵌合分歧合成多取代吲哚衍生物
通过对喹胺与硝基烯的[3 + 2]环化反应,合成了氢吲哚衍生物的两种立体异构体。在无催化剂或有 DMAP 存在的情况下,环化反应生成了含有四个连续立体中心的目标产物。通过这种方法,可以利用容易获得的构筑基块和试剂,有效地评估多取代和功能化吲哚衍生物。此外,还评估了一些氢吲哚衍生物的抗炎活性,其中三种衍生物能有效抑制 NLRP3 炎性体的激活。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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