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Synlett 2006(18): 3045-3048  
DOI: 10.1055/s-2006-951520
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Expedient Route to 3-Chlorothioxanthen-9-one-10,10-dioxide and Derivation by Palladium-Catalyzed Coupling

Pedro M. J. Lory, Anton Agarkov, Scott. R. Gilbertson*
Program in Chemical Biology, Department of Pharmacology & Toxicology, University of Texas-Medical Branch, 301 University Boulevard, Galveston, TX 77555-0650, USA
Fax: +1(409)7729700; e-Mail: srgilber@utmb.edu;
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Publication History

Received 23 February 2006
Publication Date:
25 October 2006 (online)

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Abstract

Chemistry has been developed that allows for the synthesis of a series of novel tricyclic thioxanthen-9-one-10,10-dioxides. A regioselective synthesis of the novel core substrate 3-chlorothioxanthen-9-one-10,10-dioxide was achieved in 85% yield over three steps without the need for chromatographic purification. Subsequent microwave-assisted coupling methodology afforded the desired novel 3-substituted tricyclic compounds in good to excellent yield.

Key words

catalysis - heterocycles - palladium - Suzuki reaction - thioxanthenone dioxide

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