73671-07-5

Upstream product

• 36159-76-9 4-phenyl-1-naphthol 
• 101727-37-1 2-Nitro-4-phenyl-[1]naphthol 
• 524-42-5 1,2-naphthoquinone 
• 71-43-2 benzene 
• 36159-74-7 4-phenylnaphthalen-2-ol 
• 98-80-6 phenylboronic acid 
• 18099-96-2 4-bromonaphthalene-1,2-dione 

Downstream Products

• 113057-92-4 5-phenylbenzo[a]phenazine 
• 92439-00-4 4-phenyl-1H-2-benzopyran-1-one 
• 15185-05-4 4-phenylcoumarin 

Relevant academic research and scientific papers

Rapid, Operationally Simple, and Metal-free NBS Mediated One-pot Synthesis of 1,2-Naphthoquinone from 2-Naphthol

A metal-free, one-pot synthesis of 1,2-naphthoquinone was accomplished from 2-naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1-dibromonaphthalen-2-one and subsequent transformation afforded the 1,2-naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3-dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents. (Figure presented.).

Rhodium(I)-Catalyzed Decarbonylative Aerobic Oxidation of Cyclic α-Diketones: A Regioselective Single Carbon Extrusion Strategy

A rhodium-catalyzed decarbonylative aerobic oxidation of cyclic α-diketones has been developed for the first time, where the regioselective formations of α-pyrones and isocoumarins have been achieved. The current decarbonylative aerobic oxidation pathway proceeds via the C-C bond cleavage followed by a C-O bond formation, representing a biomimetic oxidation approach to unsaturated six-membered cyclic lactones. The unique ability of rhodium catalysts to induce the decarbonylative aerobic oxidation opens up a new synthetic toolbox that utilizes the "regioselective single carbon" extrusion strategy.

Copper-catalyzed divergent oxidative pathways of 2-naphthol derivatives:: Ortho -naphthoquinones versus 2-BINOLs

Catalyst-dependent divergent pathways of 2-naphthol derivatives have been investigated. A readily available CuCl2-DMAP catalyst system promotes the aerobic oxidation of 2-naphthol derivatives to ortho-naphthoquinones whereas switching the catalyst system to Cu(OAc)2-DBN under an argon atmosphere allows the oxidative coupling of 2-naphthols to 1,1′-bi-2-naphthols (BINOLs) in good to excellent yields.

The 3-substitution of naphthalene-1,2-diones with boronic acids: A C-H functionalization approach to novel spirooxazine photochromics

The addition of alkyl and aryl boronic acids to naphthalene-1,2-diones in the presence of an excess of ammonium persulfate and catalytic silver nitrate to yield 3-functionalized naphthalene-1,2-diones is reported. The products of these reactions were then

Cd45 inhibitors

Substituted naphthalenediones in accord with structural diagram (I): compositions thereof and methods for the use thereof, for the treatment of T cell mediated conditions such as autoimmune diseases and organ graft rejection. In compounds of the invention

Synthesis and PTP1B inhibition of 1,2-naphthoquinone derivatives as potent anti-diabetic agents.

A new series of 1,2-naphthoquinone derivatives was synthesized by various synthetic methods and evaluated for their ability to inhibit protein tyrosine phosphatase 1B (PTP1B). 1,2-Naphthoquinone derivatives with substituent at R(4) position showed submicromolar inhibitory activity, and compound 24 demonstrated 10- to 60-fold selectivity against the tested phosphatases. Also, several 4-aryl-1,2-naphthoquinone derivatives with substituents at R(3), R(6), R(7), or/and R(8) showed submicromolar inhibitory activity and good plasma stability.

Potent reversible inhibitors of the protein tyrosine phosphatase CD45

The cytosolic portion of CD45, a major transmembrane glycoprotein found on nucleated hematopoietic cells, contains protein tyrosine phosphatase activity and is critical for T-cell receptor-mediated T-cell activation. CD45 inhibitors could have utility in the treatment of autoimmune disorders and organ graft rejection. A number of 9,10-phenanthrenediones were identified that reversibly inhibited CD45-mediated p-nitrophenyl phosphate (pNPP) hydrolysis. Chemistry efforts around the 9,10-phenanthrenedione core led to the most potent inhibitors known to date. In a functional assay, the compounds were also potent inhibitors of T-cell receptor-ediated proliferation, with activities in the low micromolar range paralleling their enzyme inhibition. It was also discovered that the nature of modification to the phenanthrenedione pharmacophore could affect selectivity for CD45 over PTP1B (protein tyrosine phosphatase 1B) or vice versa.

Quinones. Part 11. The Reaction of o-Aminothiophenol with o-Benzo- and o-Naphtho-quinones: A New Route to 1H-Phenothiazin-1-ones

1H-Phenothiazin-1-ones can be obtained by the condensation of o-aminothiophenol with 3,5-di-t-butyl- and 3-t-butyl-5-phenyl-o-benzoquinones.In the absence of large blocking groups the phenothiazinones are unstable.A methyl group at C-4 leads via the quinone-methide tautomer, to formation of a spiro-dimer the crystal structure of which was determined by X-ray analysis.By further reaction with o-aminothiophenol, 1H-phenothiazin-1-ones yield triphenodithiazines (benzothiazinophenothiazines). o-Naphthoquinones do not form benzo-1H-phenothiazin-1-ones with o-aminothiophenol.The parent compound yields 4-hydroxy-3H-benzophenothiazin-3-one by initial thiol addition at C-4 followed by rearrangement.

Oxidative Coupling of Quinones and Aromatic Compounds by Palladium(II) Acetate

The oxidation of 1,4-benzoquinone, 2-phenyl-1,4-benzoquinone, 1,4-naphthoquinone, and 1,2-naphthoquinone by palladium(II) acetate in acetic acid containing arenes gave the corresponding aryl-sustituted quinones.Treatment of 1,4-naphthoquinone with aromatic heterocycles such as furfural, 2-acetylfuran, methyl 2-furoate, 2-acetylthiophene, 1-(phenylsulfonyl)pyrrole, 1-(phenylsulfonyl)indole, 4-pyrone, and 1-methyl-2-pyridone in the presence of palladium acetate gave the corresponding 2-heteroaryl-substituted 1,4-naphthoquinones.

Arylation of Quinones with Arenes and Palladium Acetate

Oxidation of quinones with palladium acetate in acetic acid, which contained arenes, gave arylated quinones.