33670-73-4

Upstream product

• 90-15-3 α-naphthol 
• 68432-16-6 1(2H)-naphthalenone 
• 135-19-3 β-naphthol 
• 524-42-5 1,2-naphthoquinone 
• 7732-18-5 water 
• 606-41-7 2-amino-1-naphthol 
• 7758-99-8 copper(II) sulfate 
• 41772-23-0 1-hydroxy-2-naphthylamine hydrochloride 
• 4323-69-7 [1]naphthyl-nitro-amine 

Downstream Products

• 6336-79-4 1,2-naphthalenediol diacetate 
• 1888-41-1 2-methoxy-1-naphthol 
• 99365-86-3 4-Nitro-1,2-naphthochinon-2-diazid 

Relevant academic research and scientific papers

Solid-State Electron Beam Chemistry of Mixtures of Diazoketones in Phenolic Resins: AZ Resists

Equimolar mixtures of a 2-diazo-1-naphthaquinone and a phenolic resin are exposed to a 25-kV electron beam and UV light.The mechanism for the photochemistry is explained on the basis of the well-known Wolff rearrangement.The electron beam exposure, however, does not appear to proceed via the Wolff rearrangement but instead invokes reactions of a carbene with the phenolic resin.The carbene, formed by loss of N2 from the diazoketone, forms chemical products with the resin which are soluble in base.In essence, this explains the functioning of a large class of electron beam resists consisting of diazoketone/resin mixtures.Electron beam exposures are also performed on mixtures of 2-diazo-1-naphthoquinone in m-cresol or in benzene; the results of these experiments suggest that a major product of the electron beam induced chemistry is a substituted haphthol.

3-Naphthylindole Construction by Rhodium(II)-Catalyzed Regioselective Direct Arylation of Indoles with 1-Diazonaphthalen-2-(1H)-ones

The regioselective direct 3-arylation of indoles with 1-diazonaphthalen-2-(1H)-ones was developed by means of a rhodium(II) pivalate-catalyzed cross-coupling reaction. This procedure provided a variety of novel 3-naphthylindoles in high yield. The direct coupling of benzofuran, pyrrole or furan with 1-diazonaphthalen-2-(1H)-ones afforded 2- or 3-naphthyl substituted heterocycles.

Dissociative electron capture of diazoquinones: Matrix isolation ESR study

It is postulated that the electron beam of the AZ-type resist (those containing diazoquinones as the labile component) is initiated by dissociative electron capture producing a phenoxy radical anion and N2. Na atoms and model diazoquinone molecules, 1-oxo-2-diazonaphthoquinone, 2-oxo-1-diazonapithoquinone, and o-diazobenzoquinone, were cocondensed in argon matrices, and the Na-to-diazoquinone electron transfer was induced by mild radiation (λ > 580 nm). ESR examination of the matrices that the three diazoquinones all readily captured low-energy electrons and dissociated to yield the respective phenoxy anion radicals resulting from N2 cleavage as postulated.

Rh(II)-catalyzed formal [3+3] cycloaddition of diazonaphthoquinones and propargyl alcohols: Synthesis of 2,3-dihydronaphtho-1,4-dioxin derivatives

A Rh(II)-catalyzed formal [3+3] cyclization of diazonaphthoquinones and propargyl alcohol is reported to afford 2,3-dihydro-1,4-benzodioxins. Various terminal propargyl alcohols react with diazonapthoquinone in the presence of Rh2(OAc)4/s

Synthesis of diazonaphthoquinones from naphthols by diazo-transfer reaction with 2-azido-1,3-dimethylimidazolinium chloride

An efficient synthetic method for the synthesis of diazonaphthoquinones from naphthols is described. A variety of diazonaphthoquinones were synthesized from the corresponding naphthols by the diazo transfer with 2-azido-1,3- dimethylimidazolinium chloride prepared by the reaction of 2-chloro-1,3- dimethylimidazorinium chloride and sodium azide. Georg Thieme Verlag Stuttgart New York.

Synthesis of diazonaphthoquinones from naphthols by diazo-transfer reaction

Various orthodiazonaphthoquinones (1-diazo-2(1H)-naphthalenones and 2-diazo-1(2H)-naphthalenones) were synthesized using the diazo-transfer reaction between the appropriate naphthol and 2-azido-1,3-dimethylimidazolinium chloride (ADMC). The ADMC was prepa

Preparation of α-diazocarbonyl compounds from β-lapachone derivatives and other 1,2-naphthoquinones: Use of the 2D NMR 1H, 15N and 1H,13C HMBC techniques in assigning regiochemistry

The assignment of the diazo site in products of the reaction of p-toluenesulfonylhydrazine with β-lapachone, 3,4-dihydro-2,2-dimethyl-2H- naphtho[1,2-b]pyran-5,6-dione, and other 1,2-naphthoquinones in methanol solution at room temperature has been accomplished using 1H 13C HMBC and 1H15N HMBC NMR experiments. Only one diazo-naphthalenone product was isolated in yields ranging from 50-100% from each reaction. The site of diazo substitution of β-lapachone and derivatives is the 1-position, in contrast to substitution at the 2-position in 4-MeO-1,2-naphthoquinone. Steric factors, rather than electronic factors, control the reaction site. Along with 2-diazo-1(2H)-naphthalenone, an additional product isolated from the reaction of p-toluenesulfonylhydrazide with 1,2-naphthoquinone was 2-diazo-4-hydroxy-1(2H)-naphthalenone. Confirmation of the formation of 6-diazo-2,2-dimethyl-2,3,4,6-tetrahydro-2H-benzo[h]cromen-5- one, obtained from β-lapachone, was achieved using single crystal X-ray diffraction. Copyright

PHOTOCHEMICAL GENERATION OF KETENES. AN ULTRA-VIOLET AND INFRA-RED SPECTROSCOPIC STUDY OF 1- AND 2-DIAZONAPHTHALENONES AT 77K

Direct photolysis of 1- or 2-diazonaphthalenone and 2-diazonaphthalenone-5-sulfonyl chloride at 77K yields the respective indenoketenes which were identified by ultra-violet and infra-red spectroscopy.

A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis

Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.

Rh(iii)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds

A straightforward Rh(iii)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp3)-H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective with a wide scope and functional group tolerance. The synthetic utility was established through gram-scale synthesis and biologically active molecule construction.