Conversion of 9,10-anthraquinones to anthracenes

Criswell, Thomas R.; Klanderman, B. H.

doi:10.1021/jo00920a007

Cited by 75 publications

(43 citation statements)

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“…13 The product, 2-bromo-6-dihexylaminoanthracene (11), was treated with cuprous cyanide in DMF to afford 2-cyano-6-(dihexylamino)anthracene, 12. 18 Finally, 6-propionyl-2-(dihexylamino)anthracene (Anthradan) 13 was prepared by reaction of this cyano compound with ethylmagnesium chloride catalyzed with cuprous chloride followed by hydrolysis of the imine intermediate.…”

Section: Resultsmentioning

confidence: 99%

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Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Lord

Wang

et al. 2006

J. Org. Chem.

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We have synthesized the environment-sensitive fluorophores 2-cyano-6-dihexylaminoanthracene and 2-propionyl-6-dihexylaminoanthracene (Anthradan) starting from 2,6-diaminoanthraquinone. Anthradan is the benzologue of the well-known family of naphthalene 2-propionyl-6-dimethylaminonaphthalene (PRODAN) fluorophores. The additional spectral red shift of the anthracene avoids the autofluorescence of many biological systems and provides for more favorable excitation wavelengths for fluorescence applications. Furthermore, Anthradan exhibits polaritysensitive emission comparable to that of PRODAN and displays high quantum yields in a range of solvents. Single molecules of these anthracene-containing fluorophores have been imaged in polymer hosts as a proof-of-principle.

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Section: Resultsmentioning

confidence: 99%

“…The absorption maximum of 13 ranges from 439 (hexane) to 464 nm (ethylene glycol). Anthradan (13) and PRODAN are quite similar in their response to solvents, except Anthradan absorbs at approximately 100-nm longer wavelengths.…”

Section: Absorption and Emission Propertiesmentioning

confidence: 94%

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Lord

Wang

et al. 2006

J. Org. Chem.

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“…Reductions of 1-and 2-methyl AQ gave mixtures of 1-, 2-, 3-, and 4-methylanthrone. The only missing structure in the series, 10-methylanthrone, was not prepared because its MS was already available (17). Its spectrum displays a large M-15 signal (methyl loss stable benzyl ion); our unknown exhibited only a small M-15 mass spectral signal.…”

Section: Experimental Approach and Resultsmentioning

confidence: 98%

Trees Containing Built-In Pulping Catalysts - Final Report - 08/18/1997 - 08/18/2000

Pullman¹,

Dimmel²,

Peter³

2000

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EXECUTIVE SUMMARY: Several hardwood and softwood trees were analyzed for the presence of anthraquinonetype molecules. Low levels of anthraquinone (AQ) and anthrone components were detected using gas chromatography-mass spectroscopy and sensitive selected-ion monitoring techniques. Ten out of seventeen hardwood samples examined contained AQ-type components; however, the levels were typically below ~6 ppm. No AQs were observed in the few softwood samples that were examined. The AQs were more concentrated in the heartwood of teak than in the sapwood.The delignification of pine was enhanced by the addition of teak chips (~0.7% AQ-equivalence content) to the cook, suggesting that endogenous AQs can be released from wood during pulping and can catalyze delignification reactions.Eastern cottonwood contained AQ, methyl AQ, and dimethyl AQ, all useful for wood pulping. This is the first time unsubstituted AQ has been observed in wood extracts. Due to the presence of these pulping catalysts, rapid growth rates in plantation settings, and the ease of genetic transformation, eastern cottonwood is a suitable candidate for genetic engineering studies to enhance AQ content. To achieve effective catalytic pulping activity, poplar and cottonwood, respectively, require ~100 and 1000 times more for pulping catalysts.A strategy to increase AQ concentration in natural wood was developed and is currently being tested. This strategy involves "turning up" isochorismate synthase (ICS) through genetic engineering. Isochorismate synthase is the first enzyme in the AQ pathway branching from the shikimic acid pathway. In general, the level of enzyme activity at the first branch point or committed step controls the flux through a biosynthetic pathway. To test if the level of ICS regulates AQ biosynthesis in plant tissues, we proposed to over-express this synthase in plant cells.A partial cDNA encoding a putative ICS was available from the random cDNA sequencing project carried out with Arabidopsis thaliana. We used this putative plant ICS gene fragment to isolate and sequence a full-length ICS cDNA from Arabidopsis thaliana. The putative full-length cDNA encodes for a 569 amino acid protein of ~62kDa. This sequence represents the first full-length ICS cDNA isolated from a plant. When inserted into E. coli, our isolated cDNA over-expressed ICS protein in the insoluble inclusion bodies.A plant expression vector containing the ICS cDNA, NP II for selection on the antibiotic kanamycin, and duplicated 35S-cauliflower mosaic virus promoter were inserted into Agrobacterium tumefaciens strain GV3101. Transformation experiments for insertion of these foreign genes into Populus deltoides 'C175' resulted in eight lines able to regenerate shoots and grow roots in the presence of kanamycin. Plants from these eight lines have acclimated to growth in sterile soil and will be moved to a greenhouse environment in spring 2001. Non rooted shoots from each line are currently being multiplied by shoot culture. When enough shoot tissue and/or greenhouse plant ste...

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“…The former is not commercially available and was prepared from quinizarin also in three steps (methylation and two subsequent reductions with NaBH 4 ) following a literature method. 15 The Diels-Alder reaction did not work well in the solvents usually used for cyclization (toluene or xylene) but in refluxing acetonitrile the dehydro adduct 7 was isolated in reasonable yield. This adduct was acid-isomerised almost quantitatively to the corresponding hydroquinone derivative 8 which was effectively oxidized by (diacetoxyiodo) benzene to dimethoxy triptycene quinone 9.…”

Section: Resultsmentioning

confidence: 99%

Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione

Spyroudis¹,

Xanthopoulou²

2003

Arkivoc

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Conversion of 9,10-anthraquinones to anthracenes

Cited by 75 publications

References 0 publications

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Long-Wavelength Analogue of PRODAN: Synthesis and Properties of Anthradan, a Fluorophore with a 2,6-Donor−Acceptor Anthracene Structure

Trees Containing Built-In Pulping Catalysts - Final Report - 08/18/1997 - 08/18/2000

Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione

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