کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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5224625 | 1383523 | 2010 | 7 صفحه PDF | دانلود رایگان |
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.
Journal: Tetrahedron - Volume 66, Issue 13, 27 March 2010, Pages 2463-2469