Metal-Free Synthesis of Benzo[a]phenanthridines from Aromatic Aldehydes, Cyclohexanones, and Aromatic Amines

被引:19
|
作者
Jiang, Pingyu [1 ]
Shan, Zhifei [1 ]
Chen, Shanping [1 ]
Wang, Quanyuan [1 ]
Jiang, Shuxin [1 ]
Zheng, Haolin [1 ]
Deng, Guo-Jun [1 ,2 ]
机构
[1] Xiangtan Univ, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environmentally Friendly Chem & Applicat, Minist Educ,Coll Chem, Xiangtan 411105, Hunan, Peoples R China
[2] South China Univ Technol, Guangdong Prov Key Lab Luminescence Mol Aggregate, Guangzhou 510640, Guangdong, Peoples R China
来源
CHINESE JOURNAL OF CHEMISTRY | 2022年 / 40卷 / 03期
基金
中国国家自然科学基金;
关键词
Nitrogen heterocycles; Multicomponent reactions; Dehydroaromatization; Cyclization; Metal-free; BENZOPHENANTHRIDINE ALKALOIDS; 3-COMPONENT REACTION; PHENANTHRIDINES; DERIVATIVES; QUINOLINES; CYCLIZATION; ANNULATION; ARYLATION; PYRIDINES;
D O I
10.1002/cjoc.202100670
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Comprehensive Summary A three-component synthesis of benzo[alpha]phenanthridines from aromatic aldehydes, cyclohexanones, and aromatic amines has been developed, which is mediated by KI/DMSO/camphorsulfonic acid to afford a variety of functionalized benzo[alpha]phenanthridines in satisfactory yields. The present strategy provides a biaryl motif ortho to the nitrogen atom which has the potential to be used as ligand by further modification. With the advantages of readily available starting materials, transition-metal-free conditions, gram-scale synthesis, and broad substrate scope, this three-component protocol provides an efficient approach for the preparation of diverse benzo[alpha]phenanthridines.
引用
收藏
页码:365 / 370
页数:6
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