Cu(OAc)<sub>2</sub> mediated mild synthesis of 2-aminobenzimidazoles and 2-aminobenzoxazoles

Han, Lei; Gan, Lin-Ling; Hu, Xiangnan; Li, Wei; Zhu, Dali; Zheng, Jiecheng; Wu, Yuanhao; Yu, Yu; Zhang, Gan

doi:10.1080/00397911.2022.2065509

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2024

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Cited by 4 publications

References 19 publications

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HFIP‐Mediated Cyclodesulfurization Approach for the Synthesis of 2‐Aminobenzoxazole and 2‐Aminobenzothiazole Derivatives

Kant,

Patel,

Banerjee

et al. 2024

Asian J Org Chem

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A straightforward strategy for the synthesis of pharmaceutically active 2‐aminobenzoxazoles and 2‐aminobenzothiazoles is described by using 2‐aminophenols, 2‐aminothiophenols, and functionalized phenylisothiocyanates as the model substrates. The developed method proceeds through the HFIP‐promoted cyclodesulfurization process which allows for the efficient synthesis of these scaffolds at 60 °C of reaction temperature without the addition of a transition metal‐catalyst or hazardous solvents with excellent yields (up to 92%) of product formation. This process involves HFIP‐mediated hydrogen bonding interactions with the hydroxyl and thiol moieties, leading to bond breaking and formation during the reaction, resulting in the compounds of interest and the in situ release of H2S gas.

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HFIP‐Mediated Cyclodesulfurization Approach for the Synthesis of 2‐Aminobenzoxazole and 2‐Aminobenzothiazole Derivatives

Kant,

Patel,

Banerjee

et al. 2024

Asian J Org Chem

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Five-membered ring systems: with more than one N atom

Yet

2023

Progress in Heterocyclic Chemistry

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TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles

et al. 2022

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Cu(OAc)₂ mediated mild synthesis of 2-aminobenzimidazoles and 2-aminobenzoxazoles

Cited by 4 publications

References 19 publications

HFIP‐Mediated Cyclodesulfurization Approach for the Synthesis of 2‐Aminobenzoxazole and 2‐Aminobenzothiazole Derivatives

HFIP‐Mediated Cyclodesulfurization Approach for the Synthesis of 2‐Aminobenzoxazole and 2‐Aminobenzothiazole Derivatives

Five-membered ring systems: with more than one N atom

TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles

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Cu(OAc)2 mediated mild synthesis of 2-aminobenzimidazoles and 2-aminobenzoxazoles

Cited by 4 publications

References 19 publications

HFIP‐Mediated Cyclodesulfurization Approach for the Synthesis of 2‐Aminobenzoxazole and 2‐Aminobenzothiazole Derivatives

HFIP‐Mediated Cyclodesulfurization Approach for the Synthesis of 2‐Aminobenzoxazole and 2‐Aminobenzothiazole Derivatives

Five-membered ring systems: with more than one N atom

TBHP/KI-Promoted Oxidative Cyclization of α-Aminoketones for One-Pot Synthesis of Substituted 2-Acyloxazoles

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Product

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Cu(OAc)₂ mediated mild synthesis of 2-aminobenzimidazoles and 2-aminobenzoxazoles