PPh3-促进邻炔基硝基苯合成3-羟基-2-吲哚酮
收稿日期: 2023-04-13
修回日期: 2023-06-05
网络出版日期: 2023-06-14
基金资助
江苏省自然科学基金(BK20171449)
PPh3-Mediated Synthesis of 3-Hydroxy-2-oxindoles from o-Alkynylnitrobenzenes
Received date: 2023-04-13
Revised date: 2023-06-05
Online published: 2023-06-14
Supported by
Natural Science Foundation of Jiangsu Province-Grants(BK20171449)
3-羟基-2-吲哚酮核心结构在合成化学和药物化学中都具有重要的意义. 发现了一种新的、有效的由邻炔基硝基芳烃制备3-羟基-2-吲哚酮的碱促进方法, 该反应可在不含过渡金属的条件下进行. 对各种邻炔基硝基芳烃进行测定, 并以中等至良好的产率获得所需的产物. 由三苯基膦引发的Wittig反应和随后的偶姻重排构成了主要的反应过程.
关键词： PPh3; Wittig反应; 3-羟基-2-吲哚酮; 邻炔基硝基
赵雪纯 , 樊辉 , 徐瑶 , 廖小铭 , 张小祥 . PPh3-促进邻炔基硝基苯合成3-羟基-2-吲哚酮[J]. 有机化学, 2023 , 43(11) : 3997 -4002 . DOI: 10.6023/cjoc202304017
The 3-hydroxy-2-oxindole core structure is of considerable significance in both synthetic and medicinal chemistry. A novel and efficient base-promoted method for the preparation of 3-hydroxy-2-oxindoles from o-alkynylnitroarenes has been discovered. The reaction could be conducted under transition metal free conditions. Various o-alkynylnitroarenes were checked and the desired products were obtained in moderate to good yields. The Wittig-like reaction triggered by the PPh3 and the subsequent acyloin rearrangement constituted the main reaction process.
Key words： PPh3; Wittig reaction; 3-hydroxy-2-oxindoles; o-alkynylnitroarenes
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