Synthesis and study of 2-C- and 4-C-methylxanthones

Jain, A. C. ; Khanna, V. K. ; Seshadri, T. R. (1969) Synthesis and study of 2-C- and 4-C-methylxanthones Tetrahedron, 25 (2). pp. 275-282. ISSN 0040-4020

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2-C- and 4-C-methylxanthones with different oxygenation patterns have been synthesized by two methods: (1) nuclear methylation of 1,3-dihydroxyxanthones (I) to the corresponding 2-C-methyl derivatives (II) and (2) condensation of 2-methyl-(VI) and 4-methyl-(IX) 3,5-dimethoxyphenols with substituted salicylic acids. The 2-methylphenol (VI) gives 2-C-methyl-3-methoxy-1-hydroxyxanthones (VIII) and the 4-methylphenol (IX) gives 4-C-methyl isomers (XI). These observations might be of significance in understanding the mechanism of xanthone formation. C-Methylphloroglucinol (XII) yields exclusively 2-C-methyl-1,3-dihydroxyxanthones (IIa and XIV). The NMR spectra of these xanthones distinguish between 2-C- and 4-C-methylxanthones.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
ID Code:68183
Deposited On:02 Nov 2011 11:31
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