Cascade C–C bond cleavage/reformation and cycloaddition for the synthesis of 4-acyl 1,2,3-triazoles from β-alkyl nitroalkenes and organic azides

Zheng, Lei; Yi, Tao; Fang, Ruilin; Zhou, Zhongzhen; Wang, Can; Chen, Yunfeng

doi:10.1039/d3qo01086d

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01086d

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Cascade C–C bond cleavage/reformation and cycloaddition for the synthesis of 4-acyl 1,2,3-triazoles from β-alkyl nitroalkenes and organic azides

Lei Zheng,

Tao Yi,

Ruilin Fang

et al.

Abstract: A copper(II)-catalyzed cascade synthesis of 4-acyl 1,2,3-triazoles has been achieved from β-alkyl nitroalkenes and organic azides. This one-pot tandem strategy involves a Lewis base-promoted isomerization and subsequent copper-catalyzed selective aerobic...

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Cited by 3 publications

References 58 publications

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In Situ-Generated Formamidine as a Carbon/Nitrogen Source for Enaminone Formation: One-Pot Synthesis of Functionalized 4-Acyl-1,2,3-triazoles

Lin,

Chen,

Chien

et al. 2024

J. Org. Chem.

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N,N-Dimethylformamide was reacted with hexamethyldisilazane to generate an N,N-dimethylformimidamide intermediate; thereafter, a reaction with acetophenones/β-diketones was induced to form enaminones. The one-pot synthetic protocol described in this paper can be applied to synthesize 1,4-disubstituted 1,2,3-triazoles and 1,4,5-trisubstituted 1,2,3-triazoles, in which organic azides are used as substrates under optimized conditions. Furthermore, this protocol uses readily available materials, is nearly free of solvent, can be applied to gram-scale operations, and leads to the formation of structurally diverse products with favorable yields.

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In Situ-Generated Formamidine as a Carbon/Nitrogen Source for Enaminone Formation: One-Pot Synthesis of Functionalized 4-Acyl-1,2,3-triazoles

Lin,

Chen,

Chien

et al. 2024

J. Org. Chem.

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Ring-Opening α,β-Difunctionalization of Cyclopropanols with Azides Enables 4-Keto-Functionalized 1,2,3-Triazole Synthesis

Zhan,

Yuan,

Wei

et al. 2024

Org. Lett.

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Selective C−C bond cleavage and transformation of organic small molecules to create products of increased value are one of the central goals in organic chemistry. In this study, we have developed a novel TEMPO-mediated ring-opening α,β-difunctionalization of cyclopropyl alcohols with organic azides to prepare structurally important 4-keto-1,2,3-triazoles under metal-and additive-free conditions. This protocol not only provides a straightforward and efficient method for the synthesis of 4-ketofunctionalized 1,2,3-triazoles in one pot but also accomplishes the goal of constructing α,β-double C−N bonds via the ring opening of cyclopropyl alcohols for the first time. Additionally, the application of the skeletons of drugs and natural products and the synthesis of Kv1.5 channel blocker 4u further demonstrate the synthetic potential and practicability of this strategy.

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Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions

Li,

Jia,

Yang

et al. 2025

Org. Chem. Front.

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Cascade C–C bond cleavage/reformation and cycloaddition for the synthesis of 4-acyl 1,2,3-triazoles from β-alkyl nitroalkenes and organic azides

Abstract: A copper(II)-catalyzed cascade synthesis of 4-acyl 1,2,3-triazoles has been achieved from β-alkyl nitroalkenes and organic azides. This one-pot tandem strategy involves a Lewis base-promoted isomerization and subsequent copper-catalyzed selective aerobic...

Cited by 3 publications

References 58 publications

In Situ-Generated Formamidine as a Carbon/Nitrogen Source for Enaminone Formation: One-Pot Synthesis of Functionalized 4-Acyl-1,2,3-triazoles

In Situ-Generated Formamidine as a Carbon/Nitrogen Source for Enaminone Formation: One-Pot Synthesis of Functionalized 4-Acyl-1,2,3-triazoles

Ring-Opening α,β-Difunctionalization of Cyclopropanols with Azides Enables 4-Keto-Functionalized 1,2,3-Triazole Synthesis

Acetic acid-catalyzed synthesis of 1,5-disubstituted 1,2,3-triazoles under azide-free conditions

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