CAN-Mediated Oxidations for the Synthesis of Xanthones and Related Products

Reaction of (2,4,5-trimethoxyphenyl)(2-hydroxyphenyl)methanone with ceric ammonium nitrate furnished the xanthone, 2,3-dimethoxy-9H-xanthen-9-one. Under the same conditions the related (1,4-dimethoxynaphthalen-2-yl)(2-hydroxyphenyl)methanone resulted in the formation of 12a-methoxy-5H-benzo[c]xanthe...

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Veröffentlicht in:	Journal of organic chemistry 2010-12, Vol.75 (24), p.8701-8704
Hauptverfasser:	Johnson, Myron M, Naidoo, Jeremy M, Fernandes, Manuel A, Mmutlane, Edwin M, van Otterlo, Willem A. L, de Koning, Charles B
Format:	Artikel
Sprache:	eng
Schlagworte:	Cerium - chemistry Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Magnetic Resonance Spectroscopy Molecular Structure Naphthalenes - chemical synthesis Naphthalenes - chemistry Organic chemistry Oxidation-Reduction Preparations and properties Xanthones - chemical synthesis Xanthones - chemistry
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Beschreibung
Zusammenfassung:	Reaction of (2,4,5-trimethoxyphenyl)(2-hydroxyphenyl)methanone with ceric ammonium nitrate furnished the xanthone, 2,3-dimethoxy-9H-xanthen-9-one. Under the same conditions the related (1,4-dimethoxynaphthalen-2-yl)(2-hydroxyphenyl)methanone resulted in the formation of 12a-methoxy-5H-benzo[c]xanthenes 5,7(12aH)-dione. Other examples of this novel transformation are also outlined.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo101873v