FeCl3-Promoted Facile Synthesis of Multiply Arylated Nicotinonitriles
FeCl3-Promoted Facile Synthesis of Multiply Arylated Nicotinonitriles
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FeCl3 促进多芳基化烟腈的简便合成
DOI：
10.1055/a-1731-9464
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发表时间：
2022
期刊：
影响因子：
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通讯作者：
Nagatoshi Nishiwaki
中科院分区：
文献类型：
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作者：
Kento Iwai;Haruka Yamauchi;Soichi Yokoyama;Nagatoshi Nishiwaki
迄今已报道了许多具有生物活性的烟腈。因此，多芳基化/烷基化烟腈的合成方法的开发仍然是一个受欢迎的研究领域。在本工作中，多取代烟腈的一种新的合成策略进行了描述。在FeCl 3促进下，烯氨基腈与α，β-不饱和酮的缩合环化反应在多种底物下都能有效地进行.值得注意的是，该方法仅在三个步骤中促进获得完全和不同取代的烟腈，包括四芳基化烟腈。利用氰基的官能度，实现了烟腈的铜催化的成环反应，得到苯并[c][2，7]萘啶-5（6 H）-酮。
Many biologically active nicotinonitriles have been reported to date. Consequently, the development of synthetic methods for multiply arylated/alkylated nicotinonitriles remains a sought-after field of research. In the present work, a new synthetic strategy for multi-substituted nicotinonitriles is described. A FeCl3-promoted condensation–cyclization reaction of an enamino nitrile and α,β-unsaturated ketones proceeded efficiently with a wide range of substrates. It is noteworthy that this method facilitates access to fully and differently substituted nicotinonitriles, including tetra-arylated nicotinonitriles, in only three steps. Using the functionality of the cyano group, the copper-catalyzed annulation reaction of the nicotinonitrile was achieved to yield benzo[c][2,7]naphthyridin-5(6H)-one.