Synthesis of Dibenzo[b,f]azepines via Palladium-Catalyzed Cascade [4 + 3] Annulation of o-Alkenyl Bromoarenes and o-Bromoaniline Derivatives,Advanced Synthesis & Catalysis

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Synthesis of Dibenzo[b,f]azepines via Palladium-Catalyzed Cascade [4 + 3] Annulation of o-Alkenyl Bromoarenes and o-Bromoaniline Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2023-06-12 , DOI: 10.1002/adsc.202300336
Xin-Chen Zhan ₁ , Guo-Qiang Lin ₂ , Jian-Guo Fu ₃ , Xiaoming Ji ₄ , Shu-Sheng Zhang ₃ , Chen-Guo Feng ₃

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A cascade [4+3] annulation of o-alkenyl bromoarenes and o-bromoaniline derivatives was described. Various dibenzo[b,f]azepines with substitutions on the 10/11 position were obtained in 14–97% yields. The synthetic versatility of this protocol is highlighted by the preparation of a precursor of the drug molecule oxcarbazepine, a gram-scale synthesis, and two product transformations. Unlike previous amination/Heck sequence, this cascade process is supposed to undergo a C(vinyl), C(aryl)-palladacycle involved pathway.

中文翻译：

通过钯催化级联 [4 + 3] 邻烯基溴芳烃和邻溴苯胺衍生物的环化合成二苯并[b,f]氮杂环庚烷

描述了邻-烯基溴芳烃和邻-溴苯胺衍生物的级联[ 4+3]环化。获得了在 10/11 位点上有取代的各种二苯并[ b , f ]氮杂卓化合物，产率为 14-97%。该方案的合成多功能性通过药物分子奥卡西平前体的制备、克级合成和两种产品转化来突出。与之前的胺化/Heck 序列不同，该级联过程应该经历 C（乙烯基）、C（芳基）-钯环参与途径。

更新日期：2023-06-12

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