33753-12-7

Upstream product

• 2348-77-8 2-phenyl[1,4]naphthoquinone 
• 2684-02-8 benzenediazonium 
• 130-15-4 [1,4]naphthoquinone 
• 30069-72-8 2,3-diphenylnaphthalen-1-ol 
• 64-19-7 acetic acid 
• 70489-30-4 2,3-diphenylnaphthalene 
• 876497-43-7 1,2-bis-(dibromo-phenyl-acetyl)-benzene 
• 100-63-0 phenylhydrazine 
• 98-80-6 phenylboronic acid 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 13243-65-7 2,3-Dibromo-1,4-naphthoquinone 
• 886-38-4 diphenylcyclopropenone 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 71-43-2 benzene 

Downstream Products

• 95161-80-1 2,3-diphenyl-naphthalene-1,4-diol 
• 856197-04-1 1,2,3,4-tetraphenyl-1,4-dihydro-naphthalene-1,4-diol 
• 96003-01-9 1,4-diacetoxy-2,3-diphenyl-naphthalene 

Relevant academic research and scientific papers

Computational and crystallographic examination of naphthoquinone based diarylethene photochromes

Photochromic compounds have a lengthy history of study and a profusion of applications that stand to gain from these studies. Among the classes of photochromic compounds, diarylethenes show desirable properties including high fatigue resistance and thermal stability, thus meeting some of the most important criteria necessary to enter the realm of practical applications. Recently, photochromic diarylethenes containing quinone functionalities have demonstrated interesting optical and solid-state properties. When properly interfaced with suitable electron withdrawing groups on the aryl component, both the ring-opening and ring-closing reactions can be achieved with visible light; this is in contrast to most other diarylethenes where UV light is required for ring closure. Unfortunately, quantitative conversion from open to closed forms is not possible. In this work, we examine the relative energies of conformations of solid-state structures observed by X-ray crystallography and evaluate their thermal stabilities based on density functional theory (DFT) calculations. Time-dependent DFT (TD-DFT) is used to model the UV-vis absorption spectra of these quinone diarylethenes. We show that spectral overlap between open and closed forms is a major hindrance to full photoconversion.

A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones

straightforward and practical synthesis of 2,3-diiodo-1,4-naphthoquinone is reported. Based on the prepared diiodide, a new synthetic approach to symmetric bisubstituted 1,4-naphthoquinones via double Suzuki-Miyaura reaction at room temperature has been researched and developed. The presented general method combines broad-spectrum applicability, efficiency, and simplicity providing target materials in good to quantitative yields.

Nitrone Directing Groups in Rhodium(III)-Catalyzed C?H Activation of Arenes: 1,3-Dipoles versus Traceless Directing Groups

Functionalizable directing groups (DGs) are highly desirable in C?H activation chemistry. The nitrone DGs are explored in rhodium(III)-catalyzed C?H activation of arenes and couplings with cyclopropenones. N-tert-butyl nitrones bearing a small ortho subst

New family of antimicrobial agents derived from 1,4-naphthoquinone

Naphthalene-1,4-dione derivatives were synthesized and tested against selected bacterial strains. All the tested compounds were prepared by direct introduction of corresponding substituents into the naphthoquinone core in oxidative conditions. In this stu

Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione

Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.

Synthesis of tetraaryl-p-benzoquinones and 2,3-diaryl-1,4-naphthoquinones via Suzuki-Miyaura cross-coupling reactions

The palladium-catalyzed Suzuki-Miyaura coupling reaction of tetrabromo-p-benzoquinone and 2,3-dibromonaphthoquinone provide a convenient approach to tetraaryl-p-benzoquinones and 2,3-diarylnaphthoquinones. Suzuki-Miyaura of tetrabromo-1,4-phenylene bis(tr

Approaching ambient temperatures in 1,2-DCE to deliver efficient intermolecular D?tz benzannulation processes

Conditions have been developed that enable intermolecular D?tz benzannulations to be carried out under extremely mild conditions, using 1,2-DCE as the reaction solvent and without the requirement for any additional reaction promoters. The new protocols, at temperatures close to ambient, have been applied successfully to a range of internal and terminal alkynes with a series of aryl and alkenyl carbene complexes, resulting in good to high yields of the benzannulation products. The developed conditions did, however, return lower benzannulation yields when utilised with the traditionally more troublesome 2-furyl carbene complex. It was found that increased reaction temperatures in 1,2-DCE did deliver high yields for the processes with this heteroaryl species.

Microwave-assisted solid-phase D?tz benzannulation reaction: A facile synthesis of 2,3-disubstituted-1,4-naphthoquinones

A microwave-assisted solid-supported D?tz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1, 4-naphthoquinone derivatives in good to moderate yields with high purities.

Palladium-catalyzed cross-coupling reaction of organobismuth compounds with aryl and alkenyl chlorides

Cross-coupling reactions of hypervalent organobismuth compounds, 6-tert-butyl-5,6,7,12-tetrahydrodibenz[c,f][1,5]azabismocines, with aryl and alkenyl chlorides are efficiently catalyzed by the Pd(OAc)2/dppf [dppf = 1,1′-bis(diphenylphosphino)fe

Palladium-Catalysed Cross Coupling of Arylboronic Acids with 2-Chloro-1,4-naphthoquinones: The Synthesis of 2-Aryl- and 2,3-Bisaryl-1,4-naphthoquinones

2-Chloro-1,4-naphthoquinones underwent palladium-catalysed cross coupling reactions with arylboronic acids to give the corresponding 2-aryl-1,4-naphthoquinones. Similarly, 2,3-dichloro-1,4-naphthoquinone underwent efficient cross coupling reactions with arylboronic acids to give mono or bis adducts. The required 2-chloro-1,4-naphthoquinones were conveniently prepared from the corresponding 2-hydroxy-1,4-naphthoquinones by treatment with oxalyl chloride.