Tetrahedron ( IF 2.1 ) Pub Date : 2022-08-29 , DOI: 10.1016/j.tet.2022.132985
Fei Wang , Zhiwen Deng , Yawen Wang , Fanshu Yuan , Xing Zhang , Guo-Ping Lu , Ninghua Fu , Yamei Lin
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A KOtBu-mediated strategy for pyrimidine synthesis via selective three-component coupling reactions has been disclosed. This chemistry, in which a series of pyrimidines (20 examples) can be prepared with moderate to excellent yields, has high potential for large-scale operation owing to its metal-free conditions, atom and step economy. According to mechanistic studies, oxidative species can be generated from KOtBu or toluene in the presence of air, which can initiate the oxidation of alcohols to aldehydes (or ketones). Meanwhile, KOtBu not only promotes the condensation-cyclization process, but also triggers the dehydrogenation of dihydropyrimidine ring.
中文翻译:

KOtBu 介导的通过选择性三组分偶联反应无过渡金属合成嘧啶:一种机理见解
已经公开了一种通过选择性三组分偶联反应合成嘧啶的 KO t Bu 介导的策略。这种化学可以以中等至优异的产率制备一系列嘧啶(20 个实例),由于其无金属条件、原子和步骤经济性,具有大规模操作的巨大潜力。根据机理研究,在空气存在下,KO t Bu 或甲苯可以生成氧化物质,这可以引发醇氧化成醛(或酮)。同时,KO t Bu 不仅促进了缩合环化过程,还引发了二氢嘧啶环的脱氢。