Convenient Synthesis of Substituted 2-Phenylbenzothiazoles Using Solid-Supported Triphenylphosphine

Author: Weekes Ashley A.   Frydrych Jan   Westwell Andrew D.  

Publisher: Taylor & Francis Ltd

ISSN: 0039-7911

Source: Synthetic Communications, Vol.43, Iss.19, 2013-10, pp. : 2656-2662

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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.