The three component reaction has the advantages of simple operation and efficient reaction, in line with the principles of atomic economy and green environmental protection. At present, the arylation without transition metal catalyst is mainly divided into three types of as following: (1) the direct arylation, (2) the insertion of aryne into σ-bond or π-bond, and (3) the three-component reactions involving aryne. Compared with the direct arylation and the insertion of aryne into σ-bond or π-bond, the mechanism of three component reactions involving aryne is still unclear, and the published reviews are still lacking. In order to facilitate the scientific researchers to consult and understand the three-component reaction involved in aryne, the progresses in the three-component reaction involving aryne in recent years are reviewed. Keywords aryne; three component reaction; carbon and heteroatom; arylation 芳炔作为一类重要的反应活性中间体一直备受人 们的关注, 其参与的反应为构建碳-碳键和碳-杂键提供 了新的反应模式 [1][2][3][4][5][6] , 并且在天然产物、生物碱和药物中 间体的合成中具有广泛的应用 [7] . 自 1983 年 Kobayashi 课题组 [8] 首次报道 2-(三甲基甲硅烷基)苯基三氟甲磺酸 酯为苯炔前体, 在氟负离子作用下高效生成苯炔的方法 以来(Scheme 1), 芳炔参与的芳基化反应推动了芳炔化 学的快速发展.
Pyrimidine aryl ether derivatives have attracted widespread attention from chemists for their diverse biological activity and pharmacological properties. In this paper, a series of pyrimidine-2-arylether derivatives were synthesized with moderate to good yield by using 2-(trimethylsilyl)phenyl trifluoromethanesulfonate as a source of benzyne to react with 2-hydroxypyrimidine. Compared with the traditional method, this method has the advantages of transition-metal-free, easy preparation of 2-aryloxypyrimidine derivatives, wide functional group compatibility and high yield. Keywords benzyne; pyrimidine derivatives; nucleophilic addition; 2-phenoxy pyrimidine 嘧啶类化合物因具有多样的生物活性和药理学特 性而受到化学家的广泛关注 [1] . 其中, C2 位芳基官能团 化的嘧啶骨架是一类重要的有机结构单元, 广泛存在于 药物分子和天然产物中 [2] . 例如, 双嘧啶钠 [3] 和嘧霉胺 [4] 含有 2-芳氧基功能化的嘧啶类骨架是常用的除草剂, 这 类除草剂除草效果好, 对环境友好, 且容易被土壤中的 菌类降解. 而且, 含有芳氧基官能化的嘧啶类化合物-嘌吗啡胺, 已经被证明是合成骨激动剂的有效成分 [5] . 此外, 最新研究表明含有苯氧基嘧啶骨架的衍生物对血 小板源生长因子受体 α(PDGFRα)具有抑制作用, 从而 诱导癌细胞的凋亡和自噬 [6] . 因此, 2-芳氧基嘧啶衍生 物的合成具有重要意义. 传统上, 2-苯氧基嘧啶衍生物 的合成方法主要包括碱促进 2-(拟)卤代嘧啶与苯酚的亲 核取代反应 [7] (Scheme 1a)和 Ullmann 类型的 C-O 交叉 偶联反应 [8] (Scheme 1b). 但是, 这些反应往往需要对嘧 啶底物预官能团化, 反应过程中需要高温或者金属催化 剂, 而且反应条件复杂. 近年来, 无金属催化在有机合 成领域具有重要的应用价值. 例如, 何卫民等 [9][10] 利用 可见光催化方法, 合成了一系列具有潜在生物活性的 (杂)芳基(亚)砜、稠环喹唑啉酮类化合物. 此外, 该作者 还使用电化学引发自由基策略对异喹啉-1(2H)-的硒化 反应作了详细的研究 [11] . 这些方法的发展拓展了杂环类 化合物的构建.苯炔 [12] 作为一类重要的活性中间体, 在有机合成 中有着广泛的应用, 尤其是 Kobayashi 等 [13] 发展的 2-(三 甲基甲硅烷基
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