Synthesis and Reactivity of o‐Enoyl Arylisocyanides: Access to Phenanthridine‐8‐Carboxylate Derivatives,Advanced Synthesis & Catalysis

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Synthesis and Reactivity of o‐Enoyl Arylisocyanides: Access to Phenanthridine‐8‐Carboxylate Derivatives
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-08-02 , DOI: 10.1002/adsc.201800606
Jinxiong Cai _{1,

2} , Zhongyan Hu _{1,

2} , Yifei Li ₂ , Jun Liu ₂ , Xianxiu Xu ₁

Affiliation

Various o‐enoyl arylisocyanides were prepared from readily available reactants and found to undergo a double annulation with glutaconate to provide straightforward access to phenanthridine‐8‐carboxylates and hydrophenanthridine‐8‐carboxylates under mild aerobic conditions. In this domino transformation, two rings and three bonds were successively created. A mechanism involving tandem [3+3]‐annulation/intramolecular cyclization/ demethoxycarbonylation/aerobic oxidative aromatization sequence was proposed.

中文翻译：

邻烯丙基芳基异氰酸酯的合成和反应性：菲啶-8-羧酸盐衍生物的获得

从容易获得的反应物中制备了各种邻烯基芳基异氰酸酯，发现它们与戊二酸进行了双环化反应，从而可以在温和的好氧条件下直接获得菲啶-8-羧酸盐和氢化菲啶-8-羧酸盐。在该多米诺骨牌变换中，两个环和三个键被连续创建。提出了一种机制，涉及串联[3 + 3]-环化/分子内环化/脱甲氧基羰基化/好氧氧化芳构化顺序。

更新日期：2018-08-02

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