Sc(OTf)3-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

被引：38
|
作者：
Li, Xi-An [1 ]
Wang, Hong-Li [1 ]
Yang, Shang-Dong [1 ,2 ]
机构：
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 08期
关键词：
ACRIDONE DERIVATIVES; COUPLING REACTION; DIRECTED ORTHO; MARINE SPONGE; DIRECT ACCESS; PALLADIUM; KETONES; ALDEHYDES; METALATION; AMINATION;
D O I：
10.1021/ol400371h
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.
引用
收藏
页码：1794 / 1797
页数：4
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