Gold(I)-Catalyzed Selective Cyclization and 1,2-Shift to Prepare Pseudorutaecarpine Derivatives,Advanced Synthesis & Catalysis

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Gold(I)-Catalyzed Selective Cyclization and 1,2-Shift to Prepare Pseudorutaecarpine Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2021-11-30 , DOI: 10.1002/adsc.202101054
Wang WANG ₁ , Nan-Ying CHEN ₁ , Pei-Sen Zou ₁ , Li PANG ₁ , Dong-Liang Mo ₁ , Cheng-Xue Pan ₁ , Gui-Fa SU ₁

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A variety of pseudorutaecarpine derivatives were prepared in good to excellent yields through a gold(I)-catalyzed selective cyclization and 1,2-shift of N-alkynyl quinazolinone-tethered indoles. Mechanistic study revealed that spiroindolenines generated in situ by cyclization at the the indole C3 position underwent an alkenyl 1,2-shift to generate pseudorutaecarpine. The reaction proceeds under mild reaction conditions, has a broad substrate scope, good functional group tolerance, and gram-scalable application. Furthermore, biological evaluation showed that most of the pseudorutaecarpine scaffolds prepared exhibit anti-inflammatory activity.

中文翻译：

金 (I) 催化选择性环化和 1,2-Shift 制备伪芸香碱衍生物

通过金 (I) 催化的选择性环化和N-炔基喹唑啉酮系链吲哚的 1,2-位移，以良好至优异的产率制备了多种假芸香碱衍生物。机理研究表明，通过在吲哚C3位环化原位产生的螺二氢吲哚经过烯基1,2-移位生成假芸香碱。该反应在温和的反应条件下进行，具有广泛的底物范围、良好的官能团耐受性和克级规模的应用。此外，生物学评估表明，大多数制备的假芸香碱支架具有抗炎活性。

更新日期：2021-11-30

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