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首页> 外文期刊>Chemistry: A European journal >A Very Efficient Cerium(IV) Ammonium Nitrate Catalyzed, Four-Component Synthesis of Tetrahydropyridines and Its Application in the Concise Generation of Functionalized Homoquinolizine Frameworks
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A Very Efficient Cerium(IV) Ammonium Nitrate Catalyzed, Four-Component Synthesis of Tetrahydropyridines and Its Application in the Concise Generation of Functionalized Homoquinolizine Frameworks

机译：高效硝酸铈（IV）铵催化四氢吡啶的四组分合成及其在功能化均喹啉骨架的简捷合成中的应用

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摘要

The cerium(IV) ammonium nitrate (CAN) catalyzed, four-component reaction between primary aliphatic amines, beta-ketoesters or beta-ketothioesters, alpha,beta-unsaturated aldehydes, and alcohols provided a very efficient and atom-economical access to substituted 6-alkoxy-2-methyl-1,4,5,6-tetrahydropyridines. These materials were then transformed into homoquinolizine derivatives in excellent yields by using a two-step sequence comprised of regioselective gamma-deprotonation-allylation and ring-closing metathesis reactions. The possibility of displacing the alkoxy group by allylsilane nucleophiles, presumably through a vinylogous acyliminium intermediate species, was also demonstrated.
机译：硝酸铈（IV）硝酸铵（CAN）催化的脂肪族伯胺，β-酮酸酯或β-酮硫代酸酯，α，β-不饱和醛和醇之间的四组分反应提供了非常高效且原子经济的取代6 -烷氧基-2-甲基-1,4,5,6-四氢吡啶。然后，通过使用两步序列（包括区域选择性的γ-去质子化-烯丙基化和闭环复分解反应），将这些材料以优异的产率转化为高喹啉嗪衍生物。还证明了通过烯丙基硅烷亲核试剂取代烯丙基硅烷亲核试剂取代烷氧基的可能性。

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