Total chemical synthesis of 2-ethenyl-3,5-dimethylpyrazine and 3-ethenyl-2,5-dimethylpyrazine |
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Authors: | Toshinari H KurniadiRachid Bel Rhlid Marcel-A Juillerat Thierry GefflautJean Bolte Ralf G Berger |
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Institution: | a Department of Bioscience, Nestlé Research Center, Vers-chez-les-Blanc, P.O. Box: 44, CH-1000 Lausanne 26, Switzerland b UMR 6504, Université Blaise Pascal, F-63177 Aubière Cedex, France c Universität Hannover, Wunstorfer Str. 14, D-30453 Hannover, Germany |
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Abstract: | The aroma compounds 2-ethenyl-3,5-dimethylpyrazine 1 and 3-ethenyl-2,5-dimethylpyrazine 2 were synthesized via a new chemical route. The key steps of the synthesis involve cyclocondenzation of 1-bicyclo2.2.1]5-hepten-2-yl]-1,2-propanedione and 1,2-propanediamine, aromatization of the resulting 5,6-dihydropyrazines, and subsequent Retro-Diels-Alder reaction to generate pyrazines 1 and 2. Pyrazine 1, a powerful odorant, was obtained in large excess (8:2) when endo-1-bicyclo2.2.1]5-hepten-2-yl]-1,2-propanedione was used as intermediate substrate. |
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Keywords: | pyrazine intermediate substrate condensation |
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