Journal
TETRAHEDRON LETTERS
Volume 53, Issue 17, Pages 2202-2205Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2012.02.072
Keywords
Arynes; ortho-Hydroxychalcones; Nucleophilic; Michael addition; Cesium carbonate
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Funding
- Kansas University NIH Center of Excellence in Chemical Methodology and Library Development [P50 GM069663]
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The reaction of o-(trimethylsilyl)aryl triflates, CsF, and o-hydroxychalcones affords a general and efficient way to prepare biologically interesting 9-substituted xanthenes. This chemistry presumably proceeds by the tandem intermolecular nucleophilic attack of the phenoxide of the chalcone on the aryne and subsequent intramolecular Michael addition. The introduction of an external base, Cs2CO3, has proven beneficial in this reaction. (c) 2012 Elsevier Ltd. All rights reserved.
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