New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors |
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Authors: | Nicolas Candelon Svitlana Shinkaruk Bernard Bennetau Catherine Bennetau-Pelissero Marie-Laurence Dumartin Marie Degueil Pierre Babin |
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Institution: | a CNRS, UMR 5255 ISM, F-33405 Talence, France b Université de Bordeaux, F-33607, France c ENITA de Bordeaux, UMRS, F-33175, France |
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Abstract: | An original synthetic route to asymmetrically substituted methoxypyrazine (MP) derivatives is described. The first step of the synthesis is achieved by condensation of 1,2-aminoalcohols with Boc-protected aliphatic aminoacids followed by cycloimine formation and aromatization via chlorination. Introduction of methoxy group was then achieved by alkoxy-de-halogenation. The use of primary or secondary aminopropanol enabled the direct and selective introduction of methyl group, in 5- or 6-position, which can be easily functionalized. Aromatization of diketopiperazine, prepared from l-valine and l-glutamic acid dimethyl ester, made possible a direct introduction of a functionalized alkyl chain. These reactions are also suitable for the synthesis of naturally-occurring MPs such as wine flavor components and biologically active substances. |
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