New approach to asymmetrically substituted methoxypyrazines, derivatives of wine flavors

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• 作者：Nicolas C ; elon ; Svitlana Shinkaruk ; Bernard Bennetau ; Catherine Bennetau-Pelissero ; Marie-Laurence Dumartin ; Marie Degueil ; Pierre Babin
• 刊名：Tetrahedron
• 出版年：2010
• 出版时间：27 March 2010
• 年：2010
• 卷：66
• 期：13
• 页码：2463-2469
• 全文大小：352 K

文摘

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.