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

文献情報

出版日 2023-12-14

DOI 10.1039/D3NJ03905F

インパクトファクター 3.591

著者

Xinkun An, Haoyun Ma, Guoen Cui, Tingting Zhang, Leichuan Xu, Mingan Wang

原文を見る

要旨

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.

掲載誌

New Journal of Chemistry

CiteScore: 5.3

自己引用率: 3.7%

年間論文数: 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.

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

文献情報

おすすめジャーナル

関連文献

Functionalized polycarbonates from dihydroxyacetone: insights into the immortal ring-opening polymerization of 2,2-dimethoxytrimethylene carbonate

Preparation of jellyfish-shaped amphiphilic block-graft copolymers consisting of a poly(ε-caprolactone)-block-poly(pentafluorostyrene) ring and poly(ethylene glycol) lateral brushes

High relaxivity MRI imaging reagents from bimodal star polymers

Two dimensional size controlled confinement of poly(vinyl pyrrolidone) in the interlayer space of swelling clay mineral

An improved grafting technique for producing imprinted thin film composite beads

Facile synthesis of cross-linked patchy fluorescent conjugated polymernanoparticles by click reactions

Synthesis of microporous polymers by Friedel–Crafts reaction of 1-bromoadamantane with aromatic compounds and their surface modification

Back cover

Photo-cross-linked mPEG-poly(γ-cinnamyl-l-glutamate) micelles as stable drug carriers

Random introduction of degradable linkages into functional vinyl polymers by radical ring-opening polymerization, tailored for soft tissue engineering

こちらもおすすめ

N-乙酰基-L-精氨酸はどのように合成されますか？

カウウェルパリミタートを含む廃棄物はどのように処理すべきですか？

タテライル1,4,8,11-テトラエチルアセートの代替品はありますか？

異丁卡因を取り扱う際の実験室安全事項は何ですか？

4-氯-2-丙基吡啶を取り扱う際の実験室安全事項は何ですか？

9,10-脱水阿霉素について適用される法規ガイドラインは何ですか？

4-(3-溴苯基)噻唑-2-甲酸の物理化学的性質は何ですか？

3-(4-塩素フェニル)-3-オキセタニアミン塩酸塩はどの業界で使用されていますか？

氮卓斯汀杂质Eを取り扱う際の実験室安全事項は何ですか？

デシシボチル-n-ブチルボルテゾミブはどのように保存すればよいですか？

掲載誌

New Journal of Chemistry

おすすめ化合物

Ethyl 2-[(3-bromo-4-pyridinyl)sulfanyl]-2-methylpropanoate

Calcium hexonate 2-hydroxypropanoate (1:1:1)

Methyl 5-iodo-3-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-2-thiophenecarboxylate

1-Iodo-3,5-dinitrobenzene

6-Hydroxy-1-naphthonitrile

おすすめサプライヤー