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Synfacts 2010(2): 0151-0151
DOI: 10.1055/s-0029-1219122
DOI: 10.1055/s-0029-1219122
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Synthesis of 2-Amino-benzothiazoles
G. Shen, X. Lv, W. Bao*
Zhejiang University, P. R. of China
Further Information
Publication History
Publication Date:
21 January 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201002/lookinside/thumbnails/10.1055-s-0029-1219122-1.jpg)
Significance
The synthesis of N-substituted 2-aminobenzothiazoles by the copper(I)-catalyzed addition-cyclization reaction of 2-haloanilines and isothiocyanates is reported. The reaction is carried out under ligand-free conditions and the best results are obtained using CuI as a catalyst and K2CO3 as a base. The reaction proceeds well with electron-rich isothiocyanatobenzenes and in moderate yields with electron-deficient isothiocyanatobenzenes and benzoyl isothiocyanates. It is also successful with 2-bromoanilines and 2-bromopyridines. A mechanism involving a nucleophilic attack of the 2-haloaniline nitrogen onto the isothiocyanate followed by a ring closure under copper catalysis is proposed without evidence.