50781-46-9

Upstream product

• 90-47-1 xanth-9-one 
• 56341-31-2 2-bromo-9H-xanthene-9-one 
• 98-80-6 phenylboronic acid 
• 92-69-3 4-Phenylphenol 
• 446-52-6 2-Fluorobenzaldehyde 
• 57279-20-6 1-(2-bromophenyl)-butane-1,3-dione 
• 80234-04-4 2-phenylacrylaldehyde diethyl acetal 
• 934691-77-7 2-(biphenyl-4-yloxy)benzaldehyde 
• 17504-13-1 methyl 4-hydroxy-[1,1’-biphenyl]-3-carboxylate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 1316277-24-3 C₁₉H₁₃NO₂ 
• 1316277-18-5 C₁₉H₁₃NO₂ 
• 1316277-36-7 C₁₉H₁₃NO₃ 
• 1316277-31-2 C₁₉H₁₃NO₃ 
• 1323153-39-4 2-hydroxy-5-phenyl-2'-hydroxybenzophenone 
• 1323153-54-3 C₂₆H₂₀N₂O₃ 

Relevant academic research and scientific papers

Formation and Disproportionation of Xanthenols to Xanthenes and Xanthones and Their Use in Synthesis

A facile and versatile strategy employing TiCl4-mediated cyclization followed by a Cannizzaro reaction has been developed for the synthesis of various xanthene derivatives. The reaction proceeded smoothly to afford both xanthenes/xanthones or their sulfur derivatives and tolerated a wide range of electronically diverse substrates. Using this methodology, pranoprofen was synthesized in three steps in 59% overall yield from commercially available starting materials.

Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H cross-dehydrogenative coupling (CDC)

A Cu(0)/Selectfluor system-catalyzed intramolecular Csp2-H/Csp2-H bond cross-dehydrogenative coupling of 2-aryloxybenzaldehydes is described. A variety of substituted xanthone derivatives are synthesized in moderate to excellent yields. Reaction can also be extended to the synthesis of 9H-thioxanthen-9-one 10,10-dioxide and phenanthridin-6(5H)-ones, respectively.

Oxidative [3+3] Annulation of Atropaldehyde Acetals with 1,3-Bisnucleophiles: An Efficient Method of Constructing Six-Membered Aromatic Rings, Including Salicylates and Carbazoles

An oxidative [3+3] annulation of atropaldehyde acetals with various 1,3-bisnucleophiles was developed using either N-bromosuccinimide or copper(II) bromide as oxidizing reagent and Br?nsted or Lewis acids as catalyst. The [3+3] annulations can be considered mechanistically as oxidizing reagent-induced acid-acid-catalyzed domino reactions established through the concept of auto-tandem catalysis. Alkyl acetoacetates, α-(indol-2-yl)acetate, anilines, 1-methyl-1H-pyrazol-3-amine, ethyl 5-amino-1H-pyrazole-3-carboxylate, and 3-amino-1H-indazole can all be used as 1,3-bisnucleophiles in this type of transformation. The established reactions can very efficiently construct six-membered aromatic rings, including salicylates and carbazoles. A four-step method of synthesizing the anti-inflammatory agent diflunisal was also developed based on the oxidative [3+3] annulation reaction, and the yield was high. (Figure presented.).

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.

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.

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.

Xanthones in heterocyclic synthesis. An efficient route for the synthesis of C-3 o-Hydroxyaryl substituted 1, 2-benzisoxazoles and their N-oxides, potential scaffolds for angiotensin(II) antagonist hybrid peptides

Regioselective substitution of xanthone and its nucleophilic cleavage allow the synthesis of C-3 ohydroxyaryl substituted 1, 2-benzisoxazoles or their V-oxides by cyclodehydration or oxidative cyclization of their corresponding ketoxime precursors, respectively. Molecular modeling analysis and 1H NMR spectra indicate an intramolecular H-bonding engaging phenol OH and the isoxazole ring N atom. The Japan Institute of Heterocyclic Chemistry.

Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates

The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.

An aryl to imidoyl palladium migration process involving intramolecular C-H activation

Biologically interesting fluoren-9-one and xanthen-9-one derivatives have been prepared by a novel aryl to imidoyl palladium migration, followed by intramolecular arylation. The fluoren-9-one synthesis appears to involve both a palladium migration mechanism and a C-H activation process proceeding through an unprecedented organopalladium(IV) hydride intermediate. The results from deuterium labeling experiments are consistent with the proposed dual mechanism.