ZnCl2-Catalyzed [4+1] Annulation of Alkylthio-Substituted Enaminones and Enaminothiones with Sulfur Ylides |
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Authors: | Yuan He Jiang Lou Prof?Dr Zhengkun Yu Prof?Dr Yong-Gui Zhou |
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Institution: | Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian, 116023 P. R. China |
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Abstract: | Concise construction of furan and thiophene units has played an important role in the synthesis of potentially bioactive compounds and functional materials. Herein, an efficient Lewis acid ZnCl2 catalyzed 4+1] annulation of alkylthio-substituted enaminones is reported, that is, α-oxo ketene N,S-acetals with sulfur ylides to afford 2-acyl-3-aminofuran derivatives. In a similar fashion, 4+1] annulation of the corresponding enaminothiones, that is, α-thioxo ketene N,S-acetals, with sulfur ylides efficiently proceeded to give multisubstituted 3-aminothiophenes. This method features wide substrate scopes as well as broad functional group tolerance, offering a concise route to highly functionalized furans and thiophenes. |
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Keywords: | annulation enaminones enaminothiones sulfur ylides zinc |
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