Facile one-pot synthesis of novel imidates as multifunctional organic fluorescent materials

被引:0
作者
Liu, Feng-Ting [1 ]
Wang, Shuo [2 ]
Chen, Yong-Shun [1 ]
Miao, Jun-Ying [2 ]
Zhao, Bao-Xiang [1 ]
Lin, Zhao-Min [3 ]
机构
[1] Shandong Univ, Inst Organ Chem, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
[2] Shandong Univ, Sch Life Sci, Shandong Prov Key Lab Anim Cells & Dev Biol, Qingdao 266237, Peoples R China
[3] Shandong Univ, Hosp 2, Inst Med Sci, Jinan 250033, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 12卷 / 01期
基金
中国国家自然科学基金;
关键词
AZA-CLAISEN REARRANGEMENT; C-H ACTIVATION; CHAPMAN REARRANGEMENT; AMIDES; MECHANISM; OXIDATION; PROBE;
D O I
10.1039/d4qo01628a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Imidates have enormous applications in the synthesis of natural products and nitrogen-containing heterocyclic compounds, as well as in drug development. However, there is currently a lack of green and efficient synthesis methods for imidate compounds. We present a novel one-pot synthesis of multifunctional organic fluorescent imidates from quinolinium salt derivatives, nitrosoarenes and alcohols. This method has the advantages of operational simplicity, mild reaction conditions, metal-free catalysis, a wide substrate scope (43 examples) and excellent isolated yields (up to 93%). Meanwhile, quinolinium-imidates exhibit good fluorescence intensity and excellent chemical stability, which makes them suitable for application in living cells, and in particular, imidate 4v can target the endoplasmic reticulum with high selectivity.
引用
收藏
页码:97 / 105
页数:9
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