Novel and rapid approach for benzanthrone synthesis: BBr3-promoted annulation of 8-aryl-1-naphthoic acid derivatives
Literature Information
Publication Date
2023-12-14
DOI
10.1039/D3NJ03905F
Impact Factor
3.591
Authors
Xinkun An, Haoyun Ma, Guoen Cui, Tingting Zhang, Leichuan Xu, Mingan Wang
View Original
Abstract
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.
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Source Journal
New Journal of Chemistry
CiteScore:
5.3
Self-citation Rate:
3.7%
Articles per Year:
2153
NJC (New Journal of Chemistry) is a broad-based primary journal encompassing all branches of chemistry and its sub-disciplines. It contains full research articles, communications, perspectives and focus articles. This well-established journal, owned by the Centre National de la Recherche Scientifique (CNRS) of France, has been co-published with the Royal Society of Chemistry since January 1998. NJC is the forum for the publication of high-quality, original and significant work that opens new directions in chemistry or other scientific disciplines. In addition to having a significant chemical component, work published in NJC must demonstrate that it will have an impact on areas of research other than that of the reported work.
Recommended Compounds
1-isopropyl-3,5-dimethyl-1H-pyrazole-4-carboxylic acid
CAS Number:
1007542-01-9
Molecular Formula:
C9H14N2O2
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Methyl 5-iodo-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-2-thiophenecarboxylate
CAS Number:
1007171-35-8
Molecular Formula:
C11H14INO4S
![7-Amino-5-methyl-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one hydrochloride (1:1) structure](https://static.chemtradehub.com/structs/209/209984-32-7-9912.webp "7-Amino-5-methyl-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one hydrochloride (1:1) structure")
7-Amino-5-methyl-5,7-dihydro-6H-dibenzo[b,d]azepin-6-one hydrochloride (1:1)
CAS Number:
209984-32-7
Molecular Formula:
C15H15ClN2O
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