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Synfacts 2007(12): 1244-1244
DOI: 10.1055/s-2007-991398
DOI: 10.1055/s-2007-991398
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Synthesis of Benzothiazoles Using a Thiol Surrogate
T. Itoh*, T. Mase
Banyu Pharmaceutical Co. Ltd., Ibaraki, Japan
Further Information
Publication History
Publication Date:
22 November 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200712/lookinside/thumbnails/10.1055-s-2007-991398-1.jpg)
Significance
Reported here is a one-pot procedure for the synthesis of benzothiazoles from the reaction of 2-bromobenzanilides with 2-ethylhexyl 3-mercaptopropionate in presence of catalytic Pd2(dba)2/XantPhos. The mercaptopropionate is used as a thiol surrogate which is released from the coupled product by β-elimination for the final cyclization to benzothiazole. Neutral or electron-deficient carbonyl amides were easily cyclized under basic conditions. Anilides with EWGs and substrates with electron-rich carbonyl amides undergo effective cyclization under acidic conditions. (4-Methoxyphenyl)methanethiol may be used as an alternative thiol surrogate.