Practical chemoselective aromatic substitution: the synthesis of <i>N</i>-(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of <i>N</i>-phenylbenzenesulfonamide

Yu, Xiao; Zhu, Wenjing; Liu, Hongyan; Liu, Yi; Li, Hongshuang; Han, Junfen; Duan, Guiyun; Bai, Zhushuang; Zhang, Pengfei; Xia, Chengcai

doi:10.1039/d2ob01028c

Cited by 2 publications

(1 citation statement)

References 39 publications

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“…2-Nitro- N -phenylbenzenesulfonamide and its derivatives ( 1 ), , N -(2-nitrophenyl)benzenesulfonamide and its derivatives ( 3a – 3x ), N -(2-nitrophenyl)pyridin-2-amine ( 3ab ), and N -(2-aminophenyl)-4-methylbenzenesulfonamide ( 7 ) were commercially available or prepared by standard procedures.…”

Section: Methodsmentioning

confidence: 99%

Tandem Reduction, Ammonolysis, Condensation, and Deamination Reaction for Synthesis of Benzothiadiazines and 1-(Phenylsulfonyl)-1H-benzimidazoles

Ma²,

Zhu

et al. 2022

J. Org. Chem.

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A novel route for a SnCl 2 -promoted tandem reduction, ammonolysis, condensation, and deamination reaction which uses nitrile and 2-nitro-N-phenylbenzenesulfonamide/N-(2-nitrophenyl)benzenesulfonamide to synthesize derivatives of benzothiadiazine/1-(phenylsulfonyl)-1H-benzimidazole has been developed. The method features convenient operation and good functional group tolerance. In addition, it employs unsensitive and inexpensive SnCl 2 /i-PrOH as the reaction reagent and provides a direct approach for the synthesis of pharmaceutically important targets.

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Section: Methodsmentioning

confidence: 99%

Tandem Reduction, Ammonolysis, Condensation, and Deamination Reaction for Synthesis of Benzothiadiazines and 1-(Phenylsulfonyl)-1H-benzimidazoles

Ma²,

Zhu

et al. 2022

J. Org. Chem.

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Electrochemical Oxidative Carbon‐atom Multifunctionalization and N‐Cyanation of Imine: Synthesis of (Z)‐N′‐Cyano‐N‐carbamimidothioate

et al. 2023

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Cyanoimines (C=NÀ CN) are eliciting increased attention because of their extensive presence in medicine and biologically active molecules. This study demonstrated the use of the electrochemical oxidative carbon-atom multifunctionalization and N-cyanation of imine to synthesize (Z)-N'-cyano-N-carbamimidothioate. This multicomponent reaction showed good step economy, thereby providing a tool to construct various cyanoimines. Moreover, good functional-group tolerance and large-scale synthesis were achieved under metal-free and external-oxidant-free conditions, indicating the potential applicability of this methodology.

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Practical chemoselective aromatic substitution: the synthesis of N-(4-halo-2-nitrophenyl)benzenesulfonamide through the efficient nitration and halogenation of N-phenylbenzenesulfonamide

Abstract: A novel route involving the metal-promoted tandem nitration and halogenation of N-phenylbenzenesulfonamide to synthesize N-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives has been developed.

Cited by 2 publications

References 39 publications

Tandem Reduction, Ammonolysis, Condensation, and Deamination Reaction for Synthesis of Benzothiadiazines and 1-(Phenylsulfonyl)-1H-benzimidazoles

Tandem Reduction, Ammonolysis, Condensation, and Deamination Reaction for Synthesis of Benzothiadiazines and 1-(Phenylsulfonyl)-1H-benzimidazoles

Electrochemical Oxidative Carbon‐atom Multifunctionalization and N‐Cyanation of Imine: Synthesis of (Z)‐N′‐Cyano‐N‐carbamimidothioate

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