Novel methodology for the synthesis of xanthones
Date
2009-10-15T09:03:42Z
Authors
Naidoo, Jeremy Morgan
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Abstract
In this MSc, novel methodology for the synthesis of xanthones and related
compounds was discovered.
It was found that treatment of (1,4-dimethoxynaphthalen-2-yl)(2-
hydroxyphenyl)methanone with ceric ammonium nitrate (CAN) resulted in the
formation of 12a-methoxy-5H-benzo[c]xanthene-5,7(12aH)-dione as the product. The
structure was confirmed by X-ray crystallography.
Exposure of a related compound (2,5-dimethoxyphenyl)(2-hydroxyphenyl)methanone
to CAN afforded 2-methoxy-9H-xanthen-9-one as the major product with 4amethoxy-
2H-xanthene-2,9(4aH)-dione formed as the minor product. This reaction
sequence has opened a new door for research into xanthone synthesis at the
University of the Witwatersrand