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Synfacts 2010(4): 0396-0396  
DOI: 10.1055/s-0029-1219496
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of C9-Functionalized Xanthenes and Acridines

Contributor(s): Victor Snieckus, Wei Gan
X. Huang, T. Zhang*
Zhejiang University, Hangzhou and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 March 2010 (online)

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Significance

Reported is a synthesis of C9-functionalized xanthenes and acridines by a cascade nucleophilic addition-cyclic Michael addition of arynes with ortho-α,β-unsaturated phenols and anilines. The method appears to be most suitable for the synthesis of xanthenes (yields ranging from 70 to 90%, 9 examples) rather than for acridines (around 50% yields, 6 examples). Extension of this method to the synthesis of thioxanthenes may be anticipated.