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

Comprehensive Summary A three‐component synthesis of benzo[α]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[α]phenanthridines in satisfactory yields. The pr...

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Bibliographic Details
Published in:Chinese journal of chemistry 2022-02, Vol.40 (3), p.365-370
Main Authors: Jiang, Pingyu, Shan, Zhifei, Chen, Shanping, Wang, Quanyuan, Jiang, Shuxin, Zheng, Haolin, Deng, Guo‐Jun
Format: Article
Language:English
Subjects:
Cyclization
Dehydroaromatization
Metal‐free
Multicomponent reactions
Nitrogen heterocycles
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Summary:Comprehensive Summary A three‐component synthesis of benzo[α]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[α]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[α]phenanthridines.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.202100670