5396-28-1

Upstream product

• 41755-73-1 phenyl 2-hydroxy-3-methylbenzoate 
• 35614-21-2 (9-oxo-9H-xanthen-4-yl)acetic acid 
• 95-48-7 ortho-cresol 
• 4549-72-8 sodium o-cresolate 
• 201230-82-2 carbon monoxide 
• 3840-18-4 2-(o-tolyloxy)aniline 
• 17264-74-3 sodium 2-chlorobenzoate 
• 1374643-16-9 bis(2-methylphenyl)iodonium trifluoromethanesulfonic acid 
• 119-36-8 methyl salicylate 
• 59907-12-9 3-bromo-2-fluorotoluene 
• 90-02-8 salicylaldehyde 
• 1072-85-1 o-fluorobromobenzene 
• 824-42-0 2-methoxy-3-methylbenzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 

Downstream Products

• 1316277-25-4 C₁₄H₁₁NO₂ 
• 1316277-19-6 C₁₄H₁₁NO₂ 
• 1316277-32-3 3-[2'-hydroxy-3'-methylphenyl]-1,2-benzisoxazole 2-oxide 
• 1316277-37-8 C₁₄H₁₁NO₃ 
• 1323153-37-2 C₁₄H₁₂O₃ 
• 1323153-50-9 C₂₁H₁₈N₂O₃ 
• 26538-97-6 4-Dimethylaminomethyl-xanthen-9-one 
• 152810-91-8 N-(4-Methyl-9H-xanthen-9-yl) benzyl carbamate 
• 35614-21-2 (9-oxo-9H-xanthen-4-yl)acetic acid 
• 154420-61-8 N-(4-methyl-9H-xanthen-9-yl)-2-chloroethanamide 

Relevant academic research and scientific papers

One-step preparation of xanthones via Pd-catalyzed annulation of 1,2-dibromoarenes and salicylaldehydes

A one-step preparation of xanthones via Pd-catalyzed annulation of 1,2-dibromoarenes and salicylaldehydes was developed.

The involvement of xanthone and (E)-cinnamoyl chromophores for the design and synthesis of novel sunscreening agents

Excessive UV exposure contributes to several pathological conditions like skin burns, er-ythema, premature skin aging, photodermatoses, immunosuppression, and skin carcinogenesis. Effective protection from UV radiation may be achieved with the use of sunscreens containing UV filters. Currently used UV filters are characterized by some limitations including systemic absorp-tion, endocrine disruption, skin allergy induction, and cytotoxicity. In the research centers all over the world new molecules are developed to improve the safety, photostability, solubility, and absorption profile of new derivatives. In our study, we designed and synthesized seventeen novel molecules by combining in the structures two chromophores: xanthone and (E)-cinnamoyl moiety. The ultraviolet spectroscopic properties of the tested compounds were confirmed in chloroform solutions. They acted as UVB or UVA/UVB absorbers. The most promising compound 9 (6-meth-oxy-9-oxo-9H-xanthen-2-yl)methyl (E)-3-(2,4-dimethoxyphenyl)acrylate) absorbed UV radiation in the range 290–369 nm. Its photoprotective activity and functional photostability were further evaluated after wet milling and incorporation in the cream base. This tested formulation with compound 9 possessed very beneficial UV protection parameters (SPFin vitro of 19.69 ± 0.46 and UVA PF of 12.64 ± 0.32) which were similar as broad-spectrum UV filter tris-biphenyl triazine. Additionally, compound 9 was characterized by high values of critical wavelength (381 nm) and UVA/UVB ratio (0.830) thus it was a good candidate for broad-spectrum UV filter and it might protect skin against UVA-induced photoaging. Compound 9 were also shown to be photostable, non-cytotoxic at con-centrations up to 50 μM when tested on five cell lines, and non-mutagenic in Ames test. It also possessed no estrogenic activity, according to the results of MCF-7 breast cancer model. Addition-ally, its favorable lipophilicity (miLogP = 5.62) does not predispose it to penetrate across the skin after topical application.

A Green Nanopalladium-Supported Catalyst for the Microwave-Assisted Direct Synthesis of Xanthones

We report an efficient, selective, rapid and eco-friendly protocol for the one-step synthesis of a small xanthone library via an intermolecular catalytic coupling from readily available salicylaldehydes and 1,2-dihaloarenes under ligand-free conditions. To achieve this advantageous direct annulation, we used a novel recoverable palladium nanocatalyst supported on a green biochar under microwave irradiation. Unlike other existing palladium-based approaches, our synthetic strategy showed a greater operational simplicity, drastic reduction in reaction times, and an excellent tolerance to diverse functional groups. The reaction proceeds in very good yields and with high regioselectivity. The novel heterogeneous catalyst can be recycled and reused up to four times without significant loss of activity.

Concise synthesis of xanthones by the tandem etherification—Acylation of diaryliodonium salts with salicylates

An efficient synthetic method for multi-substituted xanthones was developed. The reaction of diaryliodonium salts and salicylates was employed for the preparation of the xanthones. This method proceeded through an intermolecular etherification-acylation t

CBr4 promoted intramolecular aerobic oxidative dehydrogenative arylation of aldehydes: application in the synthesis of xanthones and fluorenones

A simple and practical carbon tetrabromide promoted intramolecular aerobic oxidative dehydrogenative coupling reaction has been developed to provide a straightforward ring closure protocol for 2-aryloxybenzaldehydes to furnish xanthones. The reaction was performed under metal-, additive- and solvent-free conditions with good tolerance of functional groups. The present method is also applicable to the synthesis of fluorenones by using 2-arylbenzaldehydes as substrates. Preliminary studies of the reaction mechanism indicated that the reaction may proceed through a radical pathway.

Selective Preparation of Xanthones from 2-Bromofluorobenzenes and Salicylaldehydes via Palladium-Catalyzed Acylation-SNAr Approach

A regioselective pathway for the preparation of xanthones from 2-bromofluorobenzenes and salicylaldehydes has been developed. The reaction proceeded through palladium-catalyzed acylation-SNAr sequence. Good to moderate yields of the desired xanthones were prepared in one step. Based on the results of control experiments, a possible reaction mechanism has been proposed.

Synthesis of xanthones through the palladium-catalyzed carbonylation/C-H activation sequence

A series of xanthones with the dibenzo-γ-pyrone framework were synthesized through the palladium-catalyzed carbonylation/C-H activation sequence from the ortho diazonium salts of diaryl ethers in moderate to excellent yields. After screening the reaction condition, the optimal condition was 5 mol % tetrakis (triphenylphosphine) palladium (0) as the catalyst, potassium carbonate as the base, and toluene as the solvent in the presence of catalytic amount of tetrabutyl ammonium bromide under carbon monoxide atmosphere.

FeCl3 and ether mediated direct intramolecular acylation of esters and their application in efficient preparation of xanthone and chromone derivatives

The direct intramolecular acylation of esters was developed by using the combined system of FeCl3 with Cl2CHOCH3. This unique cooperative system offered a new and efficient approach to biologically important xanthone and chromone derivatives with regioselectivity. Examples were reported, and control experiments were carried out to examine the effect of the benzyl esters and Cl2CHOCH3.

One-step synthesis of xanthones catalyzed by a highly efficient copper-based magnetically recoverable nanocatalyst

A versatile and highly efficient strategy to construct a xanthone skeleton via a ligand-free intermolecular catalytic coupling of 2-substituted benzaldehydes and a wide range of phenols has been developed. For this purpose, a novel and magnetically recoverable catalyst consisting of copper nanoparticles on nanosized silica coated maghemite is presented. The reaction proceeds smoothly with easy recovery and reuse of the catalyst. The methodology is compatible with various functional groups and provides an attractive protocol for the generation of a small library of xanthones in very good yield.

Metal-free oxidative coupling: Xanthone formation via direct annulation of 2-aryloxybenzaldehyde using tetrabutylammonium bromide as a promoter in aqueous medium

A metal-free intramolecular annulation of 2-aryloxybenzaldehydes to xanthones is disclosed, which proceeds through the direct oxidative coupling of an aldehyde C-H bond and aromatic C-H bonds using tetrabutylammonium bromide (TBAB) as a promoter in aqueous medium. This strategy works smoothly in the presence of both electron-donating and electron-withdrawing groups, and displays good tolerance towards catalytically reactive substituents, thus promising further functionalizations of xanthone products.