Synthesis of possible metabolites of 2,3,7,8-tetrachlorodibenzofuran

Burka, Leo T.; Overstreet, Diane

doi:10.1021/jf00090a017

Cited by 6 publications

(4 citation statements)

References 9 publications

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“…No unique or consistent pattern was observed for methoxy proton signals which could reflect the position of the methoxy substituent in the aromatic ring. In an earlier study with the analogous derivatives of dibenzofuran, the proton signal of the methoxy group appeared downfield if the methoxy group was present at C-4 (peri to furan oxygen) rather than at the C-l-, C-2-, or C-3-position (Burka and Oberstreet, 1989).…”

Section: Resultsmentioning

confidence: 90%

Synthesis of oxygenated derivatives of 2,3,7,8-tetrachlorodibenzo-p-dioxin

Singh¹,

Kumar²

1993

J. Agric. Food Chem.

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Four monomethoxy, five dimethoxy and four dihydroxy derivatives of polychlorodibenzo-p-dioxin have been synthesized, and their physical and spectral properties (NMR and MS) have been reported. The general method for the synthesis of specific mono-and dimethoxy derivatives in reasonable yields has been found to be the condensation of 4,5-dichlorocatechol with appropriately substituted o-chloronitrobenzenes. The monomethoxy derivatives thus prepared were demethylated by boron tribromide dimethyl sulfide. Several mono-and dihydroxypolychlorodibenzo-p-dioxins have been identified as metabolites of the highly toxic environmental contaminant 2,3,7,8tetrachlorodibenzo-p-dioxin (TCDD). However, most of these metabolites have not been fully characterized due to the lack of appropriate standards. The availability of these synthetic oxygenated derivatives of TCDD can be used to establish the structure and the potential toxicity associated with these metabolites.

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Section: Resultsmentioning

confidence: 90%

Synthesis of oxygenated derivatives of 2,3,7,8-tetrachlorodibenzo-p-dioxin

Singh¹,

Kumar²

1993

J. Agric. Food Chem.

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“…Starting materials for theses syntheses would be the corresponding hydroxyl-substituted TCDFs, for example compounds 21 and 22 . The synthesis of the regioisomeric 2,4,7,8-tetrachloro-dibenzo[ b,d ]furan-3-ol ( 21 ) and 2,3,7,8-tetrachlorodibenzo[ b,d ]furan-4-ol ( 22 ), which was performed according to reported procedure [ 17 ], is briefly depicted in Scheme 2 and fully detailed in the Supporting Materials. It involves the electrophilic substitution of 2,3,6-trichloroanisole ( 20 ) by the diazonium salt from 4,5-dichloro- o -anisidine ( 19 ), followed by deprotection of the phenolic hydroxyls and subsequent intramolecular nucleophilic aromatic substitution.…”

Section: Resultsmentioning

confidence: 99%

“…Compounds S1 and 19 are described in ref. [ 17 ] but herein they were prepared differently as described in the Supplementary Materials . Compounds S3 – S6 and 21–22 were synthesized ( Supplementary Materials ) for the needs of this work according to ref.…”

Section: Methodsmentioning

confidence: 99%

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Studies towards the Synthesis of Novel 3-Aminopropoxy-Substituted Dioxins Suitable for the Development of Aptamers for Photonic Biosensor Applications

et al. 2021

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Hydroxy-substituted tetrachlorodibenzo[b,e][1,4]dioxin and tetrachlorodibenzo[b,d]furans have been synthesized using 3,4-dichloroanisole, 2,3,6-trichlorophenol and 4,5-dichlorocatechol as starting materials and electrophilic and/or nucleophilic aromatic substitution reactions for the assembly of the dibenzo[b,e][1,4]dioxin and dibenzo[b,d]furan systems. The thus-obtained phenolic compounds were then alkylated with N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde)-protected 3-bromopropan-1-amine to give the corresponding N-Dde protected 3-aminopropoxy-substituted tetrachlorodibenzo[b,e][1,4]dioxin and tetrachlorodibenzo[b,d]furans, respectively. Hydrazinolysis-mediated Dde removal from the former compound provided the corresponding amino-substituted dioxin, which was coupled to carboxy-substituted magnetic beads affording magnetic beads coated by the amino-substituted dioxin. The latter is an attractive intermediate for the development of selective single-standard DNA (ssDNA) aptamers, which constitute molecular recognition elements in photonic biosensors with potential application to the monitoring of the dangerous environmental pollutants, dioxins having serious implications in human health.

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