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Convenient synthesis of substituted 2-phenylbenzothiazoles using solid-supported triphenylphosphine

Weekes, Ashley Ann, Frydrych, Jan and Westwell, Andrew D. 2013. Convenient synthesis of substituted 2-phenylbenzothiazoles using solid-supported triphenylphosphine. Synthetic Communications 43 (19) , pp. 2656-2662. 10.1080/00397911.2012.730648

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We report an improved procedure using solid-supported triphenylphosphine for the concise synthesis of biologically relevant 2-phenylbenzothiazoles featuring a variety of substituents on both the benzothiazole and phenyl rings. Substituted 2-phenylbenzothiazoles were synthesized by heating equimolar quantities of 2-aminothiophenol disulfides with benzaldehydes and p-toluenesulfonic acid in the presence of polymer-supported triphenylphosphine in dimethylformamide/toluene. Appealing features of this new method include simple isolation of product (removal of phosphine oxide by-product by filtration), avoidance of column chromatography, and good yields of substituted 2-phenylbenzothiazole products. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Subjects: R Medicine > RS Pharmacy and materia medica
ISSN: 0039-7911
Last Modified: 04 Jun 2017 06:30

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