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- W4245202310 abstract "One of the anthraquinone classes comprises compounds with a carbonyl group. These natural or synthetic anthraquinones find their application as building blocks in the synthesis of the compounds with a biological activity. Recently, 4-substituted anthra-9,10-quinone-1-carboxylic acids ( 2 ) have been used as key intermediates in the synthesis of patented compounds ( 3 ) with anticancer activity against multidrug resistant cell lines. Although 2,7-dihydro-3H-dibenz[de,h]cinnolin-3,7-diones ( 3 ) were successfully synthetized in a small laboratory scale, several problems were observed during the preparation of their acid intermediates ( 2 ) in a multi-gram scale. The known methods for the preparation of 2 are based on the oxidation of the methyl group in anthra-9,10-quinones ( 1 ). The most common are: the oxidation with the diluted nitric acid under high pressure in a sealed tube at the temperature of 195-220 o C, the oxidation in nitrobenzene by passing chlorine gas through the reaction mixture at the temperature of 160-170 o C or in a presence of the fuming sulphuric acid. The mentioned methods require aggressive reagents and specific reaction conditions including high pressure and temperature. Thus, there was a need to find a new efficient, cost-effective and reproducible synthetic method of preparation of 2 . While searching literature it was found that the direct oxidation of alkylarenes mediated by the sodium periodate/lithium bromide combination produces benzyl acetates throughout benzyl bromides in the acetic acid, or benzylic acids in the diluted inorganic acid. Based on these results we examined a variety of reaction conditions with or without the bromine source and the oxidizing anion. As a result, a novel procedure for the preparation of highly pure 4-substituted anthra-9,10-quinone-1-carboxylic acids (HPLC > 99.5%) using oxidizing anion/ brominating reagent system was developed. It enabled 2 isolation by the simple filtration of the reaction mixture and was applied in the scale-up of 2,7-dihydro-3H-dibenz[de,h]cinnolin-3,7-dione derivatives." @default.
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- W4245202310 date "2015-11-14" @default.
- W4245202310 modified "2023-09-29" @default.
- W4245202310 title "NaIO4/Br- as a mild system for the oxidation of 1-methyl-anthra-9,10-quinones" @default.
- W4245202310 doi "https://doi.org/10.7287/peerj.preprints.1505" @default.
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