Convenient Synthesis of Substituted 2-Phenylbenzothiazoles Using Solid-Supported Triphenylphosphine |
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| Authors: | Ashley A Weekes Jan Frydrych |
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| Institution: | 1. School of Pharmacy and Pharmaceutical Sciences , Cardiff University , Cardiff , Wales , United Kingdom;2. School of Pharmacy and Pharmaceutical Sciences , Cardiff University , Cardiff , Wales , United Kingdom;3. Department of Pharmaceutical Chemistry and Drug Control , Faculty of Pharmacy, Charles University in Prague , Hradec Králové , Czech Republic |
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| Abstract: | 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. |
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| Keywords: | Antitumor agents bicyclic compounds heterocycles 2-phenylbenzothiazoles solid-supported reagent |
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