Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- and 7-membered C-ring homologues
Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- and 7-membered C-ring homologues
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氨基甲酸酯活化率的提高使得能够合成四环苯并内酰胺：8-氧代伯宾及其 5 和 7 元 C 环同系物
DOI：
10.1039/d0ob02096f
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发表时间：
2021
影响因子：
3.2
通讯作者：
Kurouchi Hiroaki
中科院分区：
文献类型：
--
作者：
Asuka Matsunami;Kazuki Takizawa;Shogo Sugano;Yusuke Yano;Hiroaki Sato;Ryo Takeuchi;松並明日香，伊藤佑太，安村勇気，鬼頭すずか，佐伯千歩，武内亮;松並明日香，尾木原渓，佐川潤，武内亮;松並明日香，尾木原渓，佐川潤，武内亮;Kurouchi Hiroaki
开发了一种直接酰胺化芳香环连接的N-氨基甲酰基四氢异喹啉底物的路线。这条路线使一般获得8-氧代小檗碱和它们的5-和7-元C-环同系物。它克服了不希望的串联副反应，导致异喹啉骨架的破坏，这不可避免地发生在我们以前报道的超强酸氨基甲酸酯活化方法。
A route to the direct amidation of aromatic-ring-tethered N-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate activation method.