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

页码：1741 / 1756

页数：16

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