Tandem isonitrile insertion/azacyclopropylidene-annulated cyclohexenone–tropone rearrangement of p-QMs and TosMIC: de novo synthesis of pyrrolotropones with anti-cancer activity

文献情報

出版日 2021-09-22

DOI 10.1039/D1QO01256H

インパクトファクター 5.281

著者

Chuan-Hua Qu, Gui-Ting Song, Jiu-Hong Huang, Run Huang, Yuan Chen, Tong Liu, Dian-Yong Tang, Zhi-Gang Xu, Zhong-Zhu Chen

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要旨

A new and general strategy for the rapid construction of pyrrolotropones via a domino process involving 1,6-nucleophilic addition, isonitrile insertion, azacyclopropylidene-annulated cyclohexenone to tropone rearrangement, and subsequent aromatization, from the reaction of para-quinone methides (p-QMs) with p-toluenesulfonylmethyl isocyanide (TosMIC) has been proposed. The reaction does not require transition metals or stoichiometric oxidants and can be performed through one-step operation promoted by a base. This method uses easy-to-synthesize p-QMs and commercially abundant TosMIC and shows excellent scalability and broad substrate scope. Furthermore, the screening of these pyrrolotropone compounds in several human cancer cell lines shows excellent anticancer activity, which validates the feasibility of this protocol for generating bioactive compounds.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

Tandem isonitrile insertion/azacyclopropylidene-annulated cyclohexenone–tropone rearrangement of p-QMs and TosMIC: de novo synthesis of pyrrolotropones with anti-cancer activity

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