6537-46-8

Usage

Uses

Used in Chemical Synthesis:
1-AZAXANTHONE is used as a reactant in chemical synthesis for its ability to participate in a wide range of organic reactions. Its unique chemical properties allow it to be a valuable component in the creation of various compounds and materials.
Used in Pharmaceutical Industry:
1-AZAXANTHONE is used as an intermediate in the pharmaceutical industry for the development of new drugs. Its chemical properties make it a promising candidate for the synthesis of various medicinal compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Research and Development:
1-AZAXANTHONE is utilized in research and development as a key compound for exploring new chemical reactions and understanding the underlying mechanisms. Its solid-state properties and reactivity contribute to the advancement of knowledge in organic chemistry and related fields.

InChI:InChI=1/C12H7NO2/c14-11-8-4-1-2-6-10(8)15-12-9(11)5-3-7-13-12/h1-7H

Upstream product

• 1438251-51-4 2-chlorophenyl 2-methoxy-3-pyridyl ketone 
• 93-15-2 1,2-dimethoxy-4-(2-propenyl)benzene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 15181-11-0 3, 5-di-tert-butyltoluene 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 106-42-3 para-xylene 
• 95-47-6 o-xylene 

Downstream Products

• 6722-09-4 5H-<1>benzopyrano<2,3-b>pyridin-5-ol 
• 54629-47-9 5-(4-benzyl-piperidin-4-yl)-5H-chromeno[2,3-b]pyridin-5-ol 
• 59303-63-8 4-benzyl-1,4-dihydro-chromeno[2,3-b]pyridin-5-one 
• 63634-00-4 5-(4-bromo-phenyl)-5H-chromeno[2,3-b]pyridin-5-ol 
• 59303-56-9 4-phenyl-1,4-dihydro-chromeno[2,3-b]pyridin-5-one 
• 59303-77-4 5-phenyl-5H-chromeno[2,3-b]pyridin-5-ol 
• 63664-03-9 5-(4-chloro-phenyl)-5H-chromeno[2,3-b]pyridin-5-ol 
• 59303-61-6 4-(4-methoxy-phenyl)-1,4-dihydro-chromeno[2,3-b]pyridin-5-one 
• 59303-83-2 5-(4-methoxy-phenyl)-5H-chromeno[2,3-b]pyridin-5-ol 
• 59303-88-7 4,5-bis-(4-methoxy-phenyl)-5H-chromeno[2,3-b]pyridine 
• 59303-58-1 4-p-tolyl-1,4-dihydro-chromeno[2,3-b]pyridin-5-one 
• 59303-90-1 4,5-di-p-tolyl-5H-chromeno[2,3-b]pyridine 
• 59303-79-6 5-p-tolyl-5H-chromeno[2,3-b]pyridin-5-ol 
• 59303-81-0 5-(4-fluoro-phenyl)-5H-chromeno[2,3-b]pyridin-5-ol 

Relevant academic research and scientific papers

Sustainable System for Hydrogenation Exploiting Energy Derived from Solar Light

Herein described is a sustainable system for hydrogenation that uses solar light as the ultimate source of energy. The system consists of two steps. Solar energy is captured and chemically stored in the first step; exposure of a solution of azaxanthone in ethanol to solar light causes an energy storing dimerization of the ketone to produce a sterically strained 1,2-diol. In the second step, the chemical energy stored in the vicinal diol is released and used for hydrogenation; the diol offers hydrogen onto alkenes and splits back to azaxanthone, which is easily recovered and reused repeatedly for capturing solar energy.

Efficient two-step access to azafluorenones and related compounds

Crystals of a lithiocuprate prepared from copper(I) chloride and lithium 2,2,6,6-tetramethylpiperidide (2 equiv) were isolated and analyzed by X-ray diffraction as (TMP)2Cu(Cl)Li2·THF. The observation of this species is consistent with its having a role in deprotocupration- aroylation. Phenyl pyridyl ketones, phenyl quinolyl ketones, and phenyl thienyl ketones were prepared in tetrahydrofuran using the lithiocuprate and aroyl chorides as electrophiles. Diaryl ketones bearing a chloro group at the 2 position (of a pyridyl or phenyl group) thus synthesized were next converted through palladium-catalyzed ring closure to polycycles of the 5H-indeno[1,2-b]pyridin-5-one, 11H-indeno[1,2-b]quinolin-11-one, 9H-indeno[2,1-c]pyridin-9-one, and 8H-indeno[2,1-b]thiophen-8-one families.

Synthesis of azafluorenones and related compounds using deprotocupration-aroylation followed by intramolecular direct arylation

The efficiency of the deprotocupration-aroylation of 2-chloropyridine using lithiocuprates prepared from CuX (X=Cl, Br) and LiTMP (TMP=2,2,6,6- tetramethylpiperidido, 2 equiv) was investigated. CuCl was identified as a more suitable copper source than CuBr for this purpose. Different diaryl ketones bearing a halogen at the 2 position of one of the aryl groups were synthesized in this way from azines and thiophenes. These were then involved in palladium-catalyzed ring closure: substrates underwent expected CH-activation-type arylation to afford fluorenone-type compounds, and were also subjected to cyclization reactions leading to xanthones, notably in the presence of oxygen-containing substituents or reagents.

Reaction pathways involved in the quenching of the photoactivated aromatic ketones xanthone and 1-azaxanthone by polyalkylbenzenes

The reactions of the photoexcited aromatic ketones, xanthone and 1-azaxanthone, with polyalkylbenzene donors yields the corresponding ketyl radicals as detected by nanosecond laser flash photolysis. On the basis of formation of these photoreduced products, the quenching of the photoexcited species is expected to occur either by a one-step hydrogen abstraction from the donor, electron transfer followed by proton transfer from the donor, or by formation of a charge-transfer type encounter complex prior to hydrogen atom transfer. The reactions of triplet xanthone and triplet 1-azaxanthone with polyalkylbenzene donors in acetonitrile were investigated to probe the effect of the nature of the triplet state and the redox properties on the relative importance of each quenching pathway. Determination of bimolecular rate constants, as well as analysis of kinetic isotope effects and ketyl radical yields, suggests that for both xanthone and 1-azaxanthone the quenching process is dominated by formation of charge-transfer encounter complexes between excited-state aromatic ketone acceptor and ground-state polyalkylbenzene donor. The reactivites of the xanthone π,π* triplet and 1-azaxanthone n,π* triplet toward these donors is shown to be governed by their reduction potentials, with their electronic configuration being unimportant to the kinetics of encounter complex formation. The only exception to this is found when sterically encumbered polyalkylbenzene donors are employed. Results with these compounds suggest that π,π* and n,π* states form encounter complexes of different structure which affects their ability to react with hindered donors. Additionally, product yields with all of the donors are controlled by both the extent of charge transfer within encounter complexes and the encounter complex structure.