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Synthesis of 2-(arylthio)benzoates by [3+3] cyclocondensations of 3-arylthio-1-silyloxy-1,3-butadienes with 3-oxo-orthoesters, 1,1,3,3-tetramethoxypropane and 1,1-bis(methylthio)-1-en-3-ones |
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| Authors: | Muhammad Imran Nasir Rasool Christine Fischer |
| Institution: | a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany b Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany c G.C. University Faisalabad, Department of Chemistry, Faisalabad, Pakistan |
| Abstract: | A variety of 2-arylthio-4-methoxybenzoates are regioselectively prepared by TiCl4-mediated 3+3] cyclocondensations of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 3-oxo-orthoesters. Unsubstituted 2-(arylthio)benzoates were prepared by Me3SiOTf-catalyzed cyclization of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 1,1,3,3-tetramethoxypropane. The TiCl4-mediated cyclization of 3-arylthio-1-trimethylsilyloxy-1,3-butadienes with 1,1-bis(methylthio)-1-en-3-ones results in regioselective formation of 2-arylthio-6-(methylthio)benzoates. |
| Keywords: | Arenes Cyclizations Diaryl sulfides Regioselectivity Silyl enol ethers |
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