Microwave-assisted transition-metal-free intramolecular Ullmann-type O-arylation in water for the synthesis of xanthones and azaxanthones

Zhang, Xiaojin; Li, Yang; Wu, Yue; Du, Jianyao; Mao, Yingle; Wang, Xiao; Luan, Shijie; Lei, Yonghua; Li, Xiang; Sun, Haopeng; You, Qidong

doi:10.1016/j.tetlet.2014.07.003

Cited by 15 publications

(9 citation statements)

References 41 publications

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“…In the presence of 2-halo-2′-hydroxybenzophenones, a transition-metal-free intramolecular Ullmann-type O-arylation reaction (Scheme 7B) can be employed for the synthesis of the corresponding xanthones 27, either using K 2 CO 3 or tetrabutylammonium hydroxide (TBAOH) as a base. 143 The latter is an efficient, rapid, and green method which uses microwave irradiation, resulting in a short reaction time and excellent yields. The O-arylation reaction proceeds smoothly, regardless of the nature of the halogen leaving group present in the aromatic moiety, with several functional groups being well-tolerated in all the examples, and extendable to the synthesis of azaxanthones.…”

Section: Synthesis Of Xanthonesmentioning

confidence: 99%

“…Azaxanthone was prepared in two minutes with an excellent yield (98%). 143 3.1.2.2 Cyclization of benzophenones to xanthones via an oxidative cyclization. Despite not being used as often as the basecatalysed intramolecular nucleophilic aromatic substitution, methodologies based on the oxidative cyclization of the benzophenone are also employed for the synthesis of xanthone derivatives.…”

Section: Synthesis Of Xanthonesmentioning

confidence: 99%

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Recent advances in the synthesis of xanthones and azaxanthones

et al. 2020

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Section: Synthesis Of Xanthonesmentioning

confidence: 99%

Section: Synthesis Of Xanthonesmentioning

confidence: 99%

Recent advances in the synthesis of xanthones and azaxanthones

et al. 2020

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“…Aminoxanthones Selective amination, ketone-assisted, ruthenium-catalyzed [161,162] Amphiphilic xanthone Condensation of phloroglucinol and 2,4,6-trihydroxybenzoic acid in the presence of Eaton's reagent [163,164] Annulated xanthones Heck reaction/double CÀ H activation/retro-DielsÀ Alder [165] Azaxanthones Regioselective, Copper catalyzed, Ullmann coupling [166][167][168][169] Benzophenone xanthones…”

Section: Derivativesmentioning

confidence: 99%

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Klein‐Júnior

Campos

Niero

et al. 2020

Chemistry & Biodiversity

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Xanthones are a class of heterocyclic natural products that have been widely studied for their pharmacological potential. In fact, they have been serving as scaffolds for the design of derivatives focusing on drug development. One of the main study targets of xanthones is their anticancer activity. Several compounds belonging to this class have already demonstrated cytotoxic and antitumor effects, making it a promising group for further exploration. This review therefore focuses on recently published studies, emphasizing their natural and synthetic sources and describing the main mechanisms of action responsible for the anticancer effect of promising xanthones.

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“…Michael and Kostanecki introduced one of the first methods for the synthesis of xanthones, which involved the distillation of a mixture of a phenol, O -hydroxybenzoic acid, and acetic anhydride [101,102]. Since then, several other routes affording higher yields and less drastic experimental conditions have been developed [103,104,105,106,107,108,109,110].…”

Section: Synthetic Carboxyxanthone Derivativesmentioning

confidence: 99%

Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives

et al. 2019

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Xanthones represent a structurally diverse group of compounds with a broad range of biological and pharmacological activities, depending on the nature and position of various substituents in the dibenzo-γ-pyrone scaffold. Among the large number of natural and synthetic xanthone derivatives, carboxyxanthones are very interesting bioactive compounds as well as important chemical substrates for molecular modifications to obtain new derivatives. A remarkable example is 5,6-dimethylxanthone-4-acetic acid (DMXAA), a simple carboxyxanthone derivative, originally developed as an anti-tumor agent and the first of its class to enter phase III clinical trials. From DMXAA new bioactive analogues and derivatives were also described. In this review, a literature survey covering the report on carboxyxanthone derivatives is presented, emphasizing their biological activities as well as their application as suitable building blocks to obtain new bioactive derivatives. The data assembled in this review intends to highlight the therapeutic potential of carboxyxanthone derivatives and guide the design for new bioactive xanthone derivatives.

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Microwave-assisted transition-metal-free intramolecular Ullmann-type O-arylation in water for the synthesis of xanthones and azaxanthones

Cited by 15 publications

References 41 publications

Recent advances in the synthesis of xanthones and azaxanthones

Recent advances in the synthesis of xanthones and azaxanthones

Xanthones and Cancer: from Natural Sources to Mechanisms of Action

Carboxyxanthones: Bioactive Agents and Molecular Scaffold for Synthesis of Analogues and Derivatives

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