Dihydro-naphthoquinone derivatives

Dihydro-1,4- and -1,2-naphthoquinone derivatives(1461 and 1463) in a mixture of ethanol and chloroform were oxidized with iron(III) chloride in dilute hydrochloric acid to naphthoquinones (1462 and 1464) (67JOC3210). 

The reaction of 2-anilino-l,4-naphthoquinone 374 with benzoylacetic acid hydrazide gives 3-hydrazino-pyrazolyl derivative 375, that is acetylated to produce 5-[[l,4-dihydro-l,4-dioxo-3-(phenylamino)-2-naphthalenyl]sulfonyl]-3-methyl-6-phenyl-5/7-pyrazolo[5,l-c][l,2,4]triazole 51. This latter derivative is also obtained in 51% yield from reaction of 374 with benzoylacetic acid hydrazide in the presence of a mixture of acetic acid-sodium acetate <2004PS(179)1907> (Scheme 39). 

Amino-1,4- and 4-amino-1,2-naphthoquinones (74 and 75) failed to react with EMME, probably because of the amide-like character of the amino group. However, their 2,3- and 3,4-dihydro derivatives (76 and 77)... 

Uses Intermediate for phthalic anhydride, naphthol, 1,4-naphthoquinone, 1,4-dihydro-naphthalene, 1,2,3,4-tetrahydronaphthalene (tetralin), decahydronaphthalene (decalin), 1-nitro-naphthalene, halogenated naphthalenes, naphthol derivatives, dyes, explosives mothballs manufacturing preparation of pesticides, fungicides, detergents and wetting agents, synthetic resins, celluloids, and lubricants synthetic tanning preservative emulsion breakers scintillation counters smokeless powders. 

In contrast to o-phenylenediamines, l,8,naphthylenediamine and most of its derivatives react with 2,6-di-tert-buty 1-1,4-benzoquinone to give perimidinespirocy-clohexadienone 11 (Scheme 5).4,6-8 The reaction occurs readily under noncatalytic conditions when refluxing propanol or toluene solutions of the components. By contrast, catalysis of the reaction with strong proton acids (e.g., /Hoi ucncsul Ionic acid) is necessary for the preparation of 2,3-dihydro-2-spiro[4(4//)-2-fert-butyl-l-naphthalenone pcrimidine 4 when 2,6-di- fcrt-buty 1-1,4-benzoquinonc is replaced in this reaction by 2-fert-butyl- 1,4-naphthoquinone. 9... 

Synthetically, compound 152 was prepared by the Friedel-Crafts procedure from furan-3,4-dicarbonyl chloride and a tetralin derivative (85JCR (S)338). 1,4-Dihydro-l,4-epoxy-5,8-naphthoquinone, when treated with 3,6-di(2-pyridyl)-l,2,4,5-tetrazine, yielded the quinone 153 (75JCS(P1)1339) derivatives of 153 are also known (74CC1034). The parent compound (153) is a stable derivative of the unstable isobenzofuran. Finally, 3-acetyl-2-furyl-1,4-benzo- (or -naphtho-) quinones are isomerized photochemically in aprotic solvents into the quionones 154 (66HCA1806). 

Irradiation of a system consisting of 2-methyl-1,4-dihydroxynaphthalene and benzophenone leads to formation of benzophenone ketyl radical and 2-methyl-naphthosemiquinone, and 1 a,7a-dihydro-1 a-methyl-1,1 -diphenyl-1 H-cyclopropa-[b]naphthalene-2,7-dione derivatives (4) in the presence of Mg(C104)2 give indenonaphthoquinones (5) (Scheme 1), by photoinduced intramolecular electron transfer in almost quantitative yield. In agreement with Rehm-Weller predictions, the rate constants for electron transfer between the triplet states of various substituted naphthoquinones and N,N-dimethylaniline (DMA) in acetonitrile solution were found to be diffusion controlled. " Using this information, it has been shown that the efficiencies of formation of naphthalene " and DMA are unity. 

The condensation of 4-aziridinyl-l,2-naphthoquinone (20) with 1,2-diaminoethane gives the benzo[/]quinoxaline 21. In simpler systems dihydro derivatives are isolated from the condensation of dicarbonyl compounds and 1,2-diaminoethane, but in this case the fully aromatic product is obtained. ... 

Carbonyl azides react with alcoholic hydroxy compounds to form the corresponding urethanes. In the same manner, ferrocenoyl azide, and 3-fe-rrocenylpropionyl azide can derivatized, hydroxy-steroids and the resultant derivatives are determined electrochemically by LC with the detection limits at subpicomole levels. 2-[2-(Azidocarbonyl)ethyl]-3-methyl-1,4-naphthoquinone (AMQ) reacts with primary and secondary alcohols to produce carbamic acid derivatives and is used in LC with BCD and FL detections. 7-Methoxycoumarin-4-carbonyl azide (7-MC-4-CON3) and 3,4-dihydro-6,7-dimethoxy-4-methyl-3-oxoquinoxaline-2-carbonyl azide (DMEQ-CON3) are also applied to LC with FL detection as precolumn reagents. 

Ethano derivative 71a as a naphth[2,3-/ isoindole precursor was prepared in two ways. The DA adduct 73 of 1,4-naphthoquinone and 1,3-cyclohexadiene was reduced with CeCla and NaBH4 and dehydrated under acidic conditions to give l,4-dihydro-l,4-ethanoanthracene (74) [72], The... 

---