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Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-09-17 , DOI: 10.3762/bjoc.16.191
Viktor M Tkachuk , Oleh O Lukianov , Mykhailo V Vovk , Isabelle Gillaizeau , Volodymyr A Sukach

The Chan–Evans–Lam reaction of 1-unsubstituted 4-fluoroalkylpyrimidin-2(1Н)-ones with arylboronic acids is reported as a facile synthetic route to hitherto unavailable N1-(het)aryl and N1-alkenyl derivatives of the corresponding pyrimidines. An efficient C–N bond-forming process is also observed by using boronic acid pinacol esters as coupling partners in the presence of Cu(II) acetate and boric acid. The 4-fluoroalkyl group on the pyrimidine ring significantly assists in the formation of the target N1-substituted products, in contrast to the 4-methyl and 4-unsubstituted substrates which do not undergo N1-arylation under similar reaction conditions.

中文翻译:

Chan-Evans-Lam 4-氟烷基嘧啶-2(1H)-一个的N1-(杂)芳基化和N1-烯基化

的赞埃文斯-Lam反应1-未取代-4- fluoroalkylpyrimidin-2(1 Н) -酮与芳基硼酸报告为简便的合成路线,以迄今不可用Ñ 1-(杂)芳基和Ñ的1-烯衍生物相应的嘧啶。在乙酸铜(II)和硼酸的存在下,通过使用硼酸频哪醇酯作为偶联伙伴,也观察到了有效的C–N键形成过程。与在相似的反应条件下不进行N 1-芳基化的4-甲基和4-未取代的底物相反,嘧啶环上的4-氟烷基大大地帮助了目标N 1-取代的产物的形成。
更新日期:2020-09-18
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