Defluorinative Diazolation-Cyclization Relay for Synthesis of Furan-Bridged Triheterocycles and Colorimetric Sensor Application

IF 3.9 2区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - A European Journal Pub Date : 2024-12-17 DOI:10.1002/chem.202404324
Man-Hang Feng, Da-Qing Chen, Shu-Ji Gao, Danhua Ge, Xiaojun Chen, Mengtao Ma, Zhi-Liang Shen, Xue-Qiang Chu
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Abstract

Polyaromatics, as the assembly of diverse cyclic π-systems, exhibit unique physicochemical properties when compared to their individual constituents. In this study, we developed a strategic connection of two azacycles via a furan bridge through a defluorinative diazolation-cyclization reaction of trifluoromethyl enones and N-heterocycles. A range of modular 2,4-furan-bridged triheterocycles (FBTHs), featuring a C3-trifluoromethyl group, was synthesized with broad substrate scope and good regioselectivity under transition metal-free conditions. This three-component protocol was achieved through successive C(sp3)-F bond functionalization of one trifluoromethyl group, which is recognized for its stability and durability. Moreover, the synthetically useful functionalities such as bromide and formyl group could be easily installed on the resulting products, and the imidazole-containing FBTH could serve as a valuable ligand in the preparation of an advanced colorimetric sensor, thereby underscoring their potential applications.

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呋喃桥接三杂环合成的脱氟重氮-环化继电器及其比色传感器应用。
多芳烃作为多种环π体系的组合体,与其单独的组分相比,具有独特的物理化学性质。在本研究中,我们通过三氟甲基烯酮和n-杂环的脱氟重唑环化反应,通过呋喃桥建立了两个氮杂环的战略性连接。在无过渡金属的条件下,合成了一系列具有c3 -三氟甲基的模块化2,4-呋喃桥接三杂环(FBTHs),具有广泛的底物范围和良好的区域选择性。这种三组分协议是通过一个三氟甲基的连续C(sp3)-F键功能化实现的,其稳定性和耐久性得到了认可。此外,溴和甲酰基等合成有用的官能团可以很容易地安装在产物上,并且含有咪唑的FBTH可以作为制备先进比色传感器的有价值的配体,从而强调了它们的潜在应用。
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来源期刊
Chemistry - A European Journal
Chemistry - A European Journal 化学-化学综合
CiteScore
7.90
自引率
4.70%
发文量
1808
审稿时长
1.8 months
期刊介绍: Chemistry—A European Journal is a truly international journal with top quality contributions (2018 ISI Impact Factor: 5.16). It publishes a wide range of outstanding Reviews, Minireviews, Concepts, Full Papers, and Communications from all areas of chemistry and related fields. Based in Europe Chemistry—A European Journal provides an excellent platform for increasing the visibility of European chemistry as well as for featuring the best research from authors from around the world. All manuscripts are peer-reviewed, and electronic processing ensures accurate reproduction of text and data, plus short publication times. The Concepts section provides nonspecialist readers with a useful conceptual guide to unfamiliar areas and experts with new angles on familiar problems. Chemistry—A European Journal is published on behalf of ChemPubSoc Europe, a group of 16 national chemical societies from within Europe, and supported by the Asian Chemical Editorial Societies. The ChemPubSoc Europe family comprises: Angewandte Chemie, Chemistry—A European Journal, European Journal of Organic Chemistry, European Journal of Inorganic Chemistry, ChemPhysChem, ChemBioChem, ChemMedChem, ChemCatChem, ChemSusChem, ChemPlusChem, ChemElectroChem, and ChemistryOpen.
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