Hyperconjugation-Driven Isodesmic Reaction of Indoles and Anilines: Reaction Discovery, Mechanism Study, and Antitumor Application

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成果类型：

期刊论文

作者：

Xiao, Yu-Qing;Fang, Kai-Xin;Zhang, Zhihan;Zhang, Chen;Li, Yu-Jie;...

通讯作者：

Lu, LQ;Tan, Y

作者机构：

[Lu, Liang-Qiu; Lu, LQ; Xiao, Yu-Qing; Zhang, Zhihan; Zhang, Bin-Jun; Wang, Bao-Cheng; Xiao, Wen-Jing; Li, Yu-Jie] Cent China Normal Univ, Coll Chem, Minist Educ, Engn Res Ctr Photoenergy Utilizat Pollut Control &, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.

[Zhang, Miao; Jiang, Yu-Qing; Zhang, Chen; Tan, Ying; Fang, Kai-Xin] Tsinghua Univ, Inst Biomed & Hlth Engn, Shenzhen Int Grad Sch, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China.

[Lu, Liang-Qiu; Lu, LQ; Xiao, Wen-Jing] Wuhan Inst Photochem & Technol, Wuhan 430082, Hubei, Peoples R China.

[Lu, Liang-Qiu; Lu, LQ] Chinese Acad Sci, Lanzhou Inst Chem Phys LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China.

[Lu, Liang-Qiu; Lu, LQ] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China.

通讯机构：

[Lu, LQ ] C

[Tan, Y ] T

Cent China Normal Univ, Coll Chem, Minist Educ, Engn Res Ctr Photoenergy Utilizat Pollut Control &, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.

Tsinghua Univ, Inst Biomed & Hlth Engn, Shenzhen Int Grad Sch, State Key Lab Chem Oncogen, Shenzhen 518055, Peoples R China.

Wuhan Inst Photochem & Technol, Wuhan 430082, Hubei, Peoples R China.

语种：

英文

关键词：

antitumor activities;hyperconjugation;quindolines;sodesmic reaction

期刊：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

ISSN：

1433-7851

年：

2024

页码：

e202408426

DOI：

10.1002/anie.202408426

基金类别：

National Key R & D Program of the Ministry of Science and Technology; National Natural Science Foundation of China [22271113, 21820102003, 91956201, 22203034]; Wuhan Institute of Photochemistry and Technology; [2023YFA1507203]

机构署名：

本校为第一机构

院系归属：

化学学院

摘要：

Isodesmic reactions, in which chemical bonds are redistributed between substrates and products, provide a general and powerful strategy for both biological and chemical synthesis. However, most isodesmic reactions involve either metathesis or functional-group transfer. Here, we serendipitously discovered a novel isodesmic reaction of indoles and anilines that proceeds intramolecularly under weakly acidic conditions. In this process, the five-membered ring of the indole motif is broken and a new indole motif is constructed on the aniline side, accompanied by the formation of a new aniline motif...

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