A gold-catalyzed cyclization/nucleophilic addition reaction of <i>o</i>-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

Luo, Wenyi; Chen, Qiaolong; Mo, Xiaoyu; Jiang, Jun; Xie, Peng

doi:10.1039/d3qo01753b

Org. Chem. Front.

2024

DOI: 10.1039/d3qo01753b

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A gold-catalyzed cyclization/nucleophilic addition reaction of o-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

Wenyi Luo,

Qiaolong Chen,

Xiaoyu Mo

et al.

Abstract: The functionalized 3-vinylindoles were obtained through the cyclization/nucleophilic addition of ynamides and o-alkynylanilines catalyzed by gold catalyst with high stereoselectivity and site-selectivity. The theoretical researches suggested that Cα of ynamides...

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A Lewis Acid-Catalyzed Cascade Synthesis of Fused N-Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives

Arandhara,

Chutia,

Biswas

et al. 2024

J. Org. Chem.

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We herein reveal a streamlined synthesis of structurally fused 6-iminoisoindoloindolones via a meticulously orchestrated cascade reaction. This process seamlessly intertwines 2-alkynylaniline and 2-formylbenzonitrile under the catalytic influence of TMSOTf, giving rise to these compounds in remarkable yields that stand as a testament to the efficiency of our approach. Moreover, the versatility of this synthetic strategy extends far beyond mere synthesis, offering a gateway to the creation of both isoindoloindolone and unprecedented diphenylbenzopyrrolizinoisoquinolinone derivatives, thereby opening new horizons in the realm of chemical innovation. Furthermore, the strategic elegance of this synthetic methodology is underscored by its potential for scale-up production and applicability across diverse chemical contexts.

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A Lewis Acid-Catalyzed Cascade Synthesis of Fused N-Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives

Arandhara,

Chutia,

Biswas

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

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A gold-catalyzed cyclization/nucleophilic addition reaction of o-alkynylanilines with ynamides: stereoselective synthesis of 3-vinylindoles

Abstract: The functionalized 3-vinylindoles were obtained through the cyclization/nucleophilic addition of ynamides and o-alkynylanilines catalyzed by gold catalyst with high stereoselectivity and site-selectivity. The theoretical researches suggested that Cα of ynamides...

Cited by 1 publication

References 35 publications

A Lewis Acid-Catalyzed Cascade Synthesis of Fused N-Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives

A Lewis Acid-Catalyzed Cascade Synthesis of Fused N-Heterocycles from 2-Alkynylanilines and 2-Formylbenzonitriles: Unveiling Iminoisoindoloindolone and Its Derivatives

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