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通过铑（III）催化偶氮苯与含氟亚胺基硫鎓叶立德的C-H [4+1]环化反应合成含氟吲唑类化合物。

Synthesis of CF-Indazoles via Rh(III)-Catalyzed C-H [4+1] Annulation of Azobenzenes with CF-Imidoyl Sulfoxonium Ylides.

作者信息

Shang Yilong, Li Chen, Wang Guiqiu, Yao Guiwei, Wu Hongliang, Chen Xun, Zhai Ruirui

机构信息

Engineering Research Center of Tropical Medicine Innovation and Transformation of Ministry of Education, International Joint Research Center of Human-Machine Intelligent Collaborative for Tumor Precision Diagnosis and Treatment of Hainan Province, Hainan Provincial Key Laboratory of Research and Development on Tropical Herbs, School of Pharmaceutical Sciences, Hainan Medical University, Haikou 571199, China.

出版信息

Molecules. 2025 Jan 5;30(1):183. doi: 10.3390/molecules30010183.

DOI:10.3390/molecules30010183
PMID:39795239
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11720978/
Abstract

An efficient Rh(III)-catalyzed C-H activation of azobenzenes and subsequent [4+1] cascade annulation with CF-imidoyl sulfoxonium ylides was developed, yielding diverse CF-indazoles. This protocol featured easily available starting materials, excellent functional group tolerance and high efficiency. Moreover, the antitumor activities of selected CF-indazoles against human cancer cell lines were also studied, and the results indicated that several compounds displayed considerable antiproliferative activities.

摘要

开发了一种高效的铑（III）催化的偶氮苯C-H活化反应，随后与CF-亚胺基锍叶立德进行[4+1]串联环化反应，生成多种CF-吲唑。该方法具有起始原料易得、官能团耐受性好和效率高的特点。此外，还研究了所选CF-吲唑对人癌细胞系的抗肿瘤活性，结果表明几种化合物表现出相当可观的抗增殖活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/b725e802cb09/molecules-30-00183-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/3cdaa10a0ba9/molecules-30-00183-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/14de4d33675f/molecules-30-00183-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/9a2d957d30c3/molecules-30-00183-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/b725e802cb09/molecules-30-00183-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/3cdaa10a0ba9/molecules-30-00183-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/14de4d33675f/molecules-30-00183-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/9a2d957d30c3/molecules-30-00183-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/004f/11720978/b725e802cb09/molecules-30-00183-sch003.jpg

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本文引用的文献

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Copper-Catalyzed Defluorinative [3 + 2] Cyclization of Amidines and Trifluoromethyl Carbenoids for the Synthesis of 5-Fluoroimidazoles.铜催化脒与三氟甲基类卡宾的脱氟[3+2]环化反应合成5-氟咪唑
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A quick access to CF-containing functionalized benzofuranyl, benzothiophene and indolyl heterocycles under catalyst-free conditions.在无催化剂条件下快速获得含碳氟化合物的官能化苯并呋喃基、苯并噻吩基和吲哚基杂环化合物。
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Recent advances in the synthesis of trifluoromethyl-containing heterocyclic compounds trifluoromethyl building blocks.
含三氟甲基杂环化合物——三氟甲基砌块合成的最新进展
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Rhodium(III)-Catalyzed Coupling of Quinolin-8-carboxaldehydes with CF-Imidoyl Sulfoxonium Ylides by Chelation-Assisted C(sp)-H Bond Activation for the Synthesis of Trifluoromethyl-Substituted Enaminones.铑（III）催化喹啉-8-甲醛与CF-亚胺基硫鎓叶立德通过螯合辅助C（sp）-H键活化反应合成三氟甲基取代的烯胺酮
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