Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

被引：21
作者：
Yata, Tetsuji [2 ]
Kita, Yuji [2 ]
Nishimoto, Yoshihiro [1 ]
Yasuda, Makoto [2 ]
机构：
[1] Osaka Univ, Grad Sch Engn, Ctr Open Innovat Res & Educ COiRE, Frontier Res Base Global Young Researchers, 2-1 Yamadaoka, Suita, Osaka 5650871, Japan
[2] Osaka Univ, Grad Sch Engn, Dept Appl Chem, 2-1 Yamadaoka, Suita, Osaka 5650871, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期
关键词：
UNUSUAL FLUORESCENT PROPERTIES; ORGANOTIN COMPOUNDS; FACILE SYNTHESIS; ALPHA-PYRONES; ACIDS; FUNCTIONALIZATION; CYCLOADDITION; CONSTRUCTION; ISOCOUMARINS; DIMERIZATION;
D O I：
10.1021/acs.joc.9b02186
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The oxyindation of carbonyl-ene-yne compounds with indium trihalides proceeded efficiently to give di-, tri-, and tetrasubstituted 2-pyrones bearing a carbon-indium bond. The metalated 2-pyrone and a zwitterion intermediate were identified by X-ray crystallographic analysis. The application of organoindium compounds to oxidation or cross-coupling provided easy access to various multifunctionalized 2-pyrones. Some 2-pyrone derivatives show intense fluorescence only in the solid state (aggregation-induced emission).
引用
收藏
页码：14330 / 14341
页数：12
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