Summary
The two stage process of ortho-oxidation is applied to partial methyl ethers of gossypetin in order to introduce a new hydroxyl in the 6 position. The pentamethyl ether with a free hydroxyl in the 7- position does not react with hexamine. On the other hand, its isomer with a free 5-hydroxyl yields a mixture of products, one of which is the 6-aldehyde which could be oxidised by means of hydrogen peroxide. A more satisfactory procedure is to use the tetramethyl ether having the 5 and 8 hydroxyls free. It yields only the 6-aldehyde and subsequent oxidation with hydrogen peroxide leads to the formation of 5∶6∶8-trihydroxy compound. The products are useful partial methyl ethers and yield 6∶8-dihydroxy-quercetin on demethylation and its heptamethyl ether on methylation.
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Rao and SeshadriProc. Ind. Acad. Sci.,A, 1947,26, 18.
Row, Seshadri and ThiruvengadamIbid., 1947,26, 18. Rao and SeshadriIbid. Proc. Ind. Acad. Sci.,A, 1948,28, 210.
Seshadri and VenkateswarluIbid., 1946,23, 192. Murti, Row and SeshadriIbid. Proc. Ind. Acad. Sci.,A, 1946,24, 233. Sastri and SeshadriIbid. Proc. Ind. Acad. Sci.,A, 1946,24, 238.
Baker, Nodzu and RobinsonJ.C.S., 1929, 74.
Rao, Rao and SeshadriProc. Ind. Acad. Sci., A., 1944,19, 88.
Rangaswami and SeshadriIbid., 1939,9, 1, and 526; 1941,14, 547.
Rao and SeshadriIbid.,, 1947,25, 417.
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Murti, V.V.S., Seshadri, T.R. Nuclear oxidation in flavones and related compounds. Proc. Indian Acad. Sci. (Math. Sci.) 29, 221–226 (1949). https://doi.org/10.1007/BF03172451
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DOI: https://doi.org/10.1007/BF03172451