Novel and rapid approach for benzanthrone synthesis: BBr3-promoted annulation of 8-aryl-1-naphthoic acid derivatives

被引：2
|
作者：
An, Xinkun [1 ]
Ma, Haoyun [1 ]
Cui, Guoen [1 ]
Zhang, Tingting [1 ]
Xu, Leichuan [1 ]
Wang, Mingan [1 ]
机构：
[1] China Agr Univ, Coll Sci, Dept Appl Chem, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China
来源：
NEW JOURNAL OF CHEMISTRY | 2024年 / 48卷 / 04期
基金：
中国国家自然科学基金;
关键词：
ANTIMICROBIAL ACTIVITY; OXOAPORPHINE ALKALOIDS; AZADIRACHTIN; 3-NITROBENZANTHRONE; 3-AMINOBENZANTHRONE; FLUORESCENT; CONCISE; CELLS;
D O I：
10.1039/d3nj03905f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The synthesis of 3-methoxy-benzanthrones was achieved in two steps by Suzuki-Miyaura coupling and BBr3-promoted Friedel-Crafts acylation under mild conditions with an overall yield of 17-74% and tolerance toward various substrates using commercially available reagents. The competitive mechanism between demethylation and Friedel-Crafts acylation was first rationalized via a deuterium-labelling experiment and DFT calculations. Basic photochemical characteristics of 3-methoxy-benzanthrones and 3-hydroxy benzanthrones were investigated, and the benzanthrones were found to possess excellent photochemical properties. Additionally, using this novel strategy, alkaloid oxoglaucine with a similar tetracyclic skeleton was successfully synthesized with a 70% overall yield via two steps.
引用
收藏
页码：1741 / 1756
页数：16
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