Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

Organics Pub Date : 2024-04-02 DOI:10.3390/org5020004
Zhao-Hua Chen, Shijin Yu, Wen-Jin Xu, Miao-Xin Li, Yong Zeng, Si-Wei Deng, Jian-Yun Lin, Zhao-Yang Wang
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引用次数: 1

Abstract

Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize a series of trisubstituted olefin-type compounds 3 simultaneously bearing with the structure of two N-heterocyclic rings in the absence of transition metal catalysts with a yield of 62–86%. The optimal reaction conditions were systematically explored, and the structure of the obtained compounds 3 were well characterized with 1H NMR, 13C NMR, X-ray single-crystal and HR-MS. The preliminary observation showed that, in the presence of base, mucobromic acid 1 reacts as its ring-opening structure, and the successive nucleophilic substitution reaction and Michael addition reaction can generate the target product 3. Considering that the aldehyde group in the molecular structure of the trisubstituted olefin-type compounds 3 may react with malononitrile, we carried out some relevant investigations so as to realize the visual detection of malononitrile. Interestingly, among the products, compounds 3a–3c can be prepared in portable test strips through a simple process and used to achieve the naked-eye detection of malononitrile in environmental systems as designed.
含 N-杂环的新型三取代烯烃类探针分子的合成及其在检测丙二腈中的应用
最近,三取代烯烃类探针分子的构建引起了许多研究人员的关注。然而,同时合成含有两个 N-杂环的三取代烯烃型探针却鲜有报道。在本研究中,我们首先从价格低廉的粘溴酸 1 和 N-杂环化合物 2 开始,利用简单的一步反应,在无过渡金属催化剂的条件下同时合成了一系列具有两个 N-杂环结构的三取代烯烃类化合物 3,收率高达 62-86%。系统地探索了最佳反应条件,并用 1H NMR、13C NMR、X 射线单晶和 HR-MS 对所获化合物 3 的结构进行了表征。初步观察结果表明,在碱存在的条件下,粘溴酸 1 以其开环结构发生反应,通过连续的亲核取代反应和迈克尔加成反应生成目标产物 3。考虑到三取代烯烃类化合物 3 分子结构中的醛基可能会与丙二腈发生反应,我们进行了相关研究,以实现对丙二腈的目视检测。有趣的是,在这些产物中,化合物 3a-3c 可以通过简单的工艺制备成便携式试纸,并按设计用于实现环境系统中丙二腈的肉眼检测。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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