639. Synthesis of fluoranthenes. Part V. 11-Methoxyfluoranthene

Hawkins, John L.; Tucker, S. Horwood

doi:10.1039/jr9500003286

Cited by 4 publications

(3 citation statements)

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“…Reagent grade benzanthrone was purchased from Tokyo Kasei Kogyo Co. Ltd. and used after recrystallization from ethanol (purity >99.9%). Isomeric mono-and dinitrobenzanthrones used as reference compounds were prepared from appropriately substituted methyl nitro-2iodobenzoates 9 and nitro-1-iodonaphthalenes 10 via the reaction sequence involving the Ullmann coupling and intramolecular Friedel-Crafts ring closure (17)(18)(19) as illustrated in Scheme 2. Details of the preparation as well as physical properties of these and related compounds are reported elsewhere (20).…”

Section: Methodsmentioning

confidence: 99%

3-Nitrobenzanthrone, a Powerful Bacterial Mutagen and Suspected Human Carcinogen Found in Diesel Exhaust and Airborne Particulates

Enya¹,

Suzuki²,

Watanabe³

et al. 1997

Environ. Sci. Technol.

276

229

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3-Nitrobenzanthrone (3-nitro-7H-benz[d,e]anthracen-7one) was isolated from the organic extracts of both diesel exhaust and airborne particles and was identified as a new class of powerful direct mutagen. Its mutagenicity by Ames Salmonella assay is very high (208 000 revertants/ nmol in Salmonella typhimurium TA98 and 6 290 000 revertants/ nmol in YG1024) and compares with that of 1,8-dinitropyrene, which is the direct mutagen of strongest activity (257 000 revertants/nmol in TA98 and 4 780 000 revertants/nmol in YG1024) so far reported in the literature. The new mutagen was also shown to induce micronuclei in mouse peripheral blood reticulocytes after intraperitoneal administration (micronucleated reticulocytes, 0.64% against 25 mg/kg dose after 48 h), suggesting its potential genotoxicity to mammalians. 3-Nitrobenzanthrone is most likely to be formed not only during the combustion process of fossil fuels but also from the atmospheric reaction between benzanthrone and lower oxides of nitrogen, since the latter ketone was found to be nitrated quite easily under an artificial atmosphere containing gaseous NO 2 (10 ppm) and O 3 (5 ppm) to produce the powerfully mutagenic 3-nitro derivative as the major product, along with several other isomeric mononitrobenzanthrones and dinitro descendants as minor products.

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Section: Methodsmentioning

confidence: 99%

3-Nitrobenzanthrone, a Powerful Bacterial Mutagen and Suspected Human Carcinogen Found in Diesel Exhaust and Airborne Particulates

Enya¹,

Suzuki²,

Watanabe³

et al. 1997

Environ. Sci. Technol.

276

229

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“…We obtained 1-(2,6-dinitrophenyl)naphthalene ( 4 ) through crossed Ullmann condensation between 1-iodonaphthalene and 1-chloro-2,6-dinitrobenzene in the presence of copper bronze. 32 The PtO 2 /H 2 reduction 33 of 4 led to the corresponding diamine 5 in high yield, with product formation confirmed through NMR and mass spectral analyses. Although 5 has been reported as a byproduct from the action of hydrazines on β-naphthol in the presence of bisulphite, 34 its efficient synthesis and characterization have not been discussed previously.…”

Section: Resultsmentioning

confidence: 89%

Section: Synthesis and Structural Characterizationmentioning

confidence: 99%

Dynamic induction of enantiomeric excess from a prochiral azobenzene dimer under circularly polarized light

et al. 2015

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ThePschorr Synthesis and Related Diazonium Ring Closure Reactions

DeTar

2011

Organic Reactions

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In the middle 1890s, three groups of chemists independently discovered a new cyclization reaction of certain appropriately constituted diazonium salts. Fischer and Schmidt reported that an aqueous solution of 2‐benzylbenzenediazonium chloride furnished fluorene on heating. Graebe and Ullman reported that 2‐benzoylbenzenediazonium chloride yielded fluorenone and Staedel reported a somewhat similar result from the action of nitrous acid on 2,2'‐diaminbenozpehnone, a reaction that produced a little 1‐hydroxyfluorenone. Two years later, Robert Pschorr applied the ring closure reaction to the diazonium salt derived from trans‐2‐amino‐alpha‐phenylcinnamic acid to obtain phenanthrene‐9‐carboxylic acid. The principal utility of these cyclizations reactions has been the synthesis of substituted ring structures in which the positions of the substituents are known.

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639. Synthesis of fluoranthenes. Part V. 11-Methoxyfluoranthene

Cited by 4 publications

References 0 publications

3-Nitrobenzanthrone, a Powerful Bacterial Mutagen and Suspected Human Carcinogen Found in Diesel Exhaust and Airborne Particulates

3-Nitrobenzanthrone, a Powerful Bacterial Mutagen and Suspected Human Carcinogen Found in Diesel Exhaust and Airborne Particulates

Dynamic induction of enantiomeric excess from a prochiral azobenzene dimer under circularly polarized light

ThePschorr Synthesis and Related Diazonium Ring Closure Reactions

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