Electrochemical-Induced C–N Bond Formation: A New Method to Synthesis (<i>Z</i>)-Quinazolinone Oximes Using Primary Amines and Quinazolin-4(3<i>H</i>)-one

Zong, Zhi-Min; Zhang, Lizhu; Li, Gan-Peng; Wang, Wei; Zhao, Xiao-Jing; He, Yonghui

doi:10.1021/acs.orglett.4c00107

Org. Lett.

2024

DOI: 10.1021/acs.orglett.4c00107

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Electrochemical-Induced C–N Bond Formation: A New Method to Synthesis (Z)-Quinazolinone Oximes Using Primary Amines and Quinazolin-4(3H)-one

Zhi-Min Zong,

Lizhu Zhang,

Gan-Peng Li

et al.

Abstract: sı Supporting InformationThe Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c00107.Experimental details and data, including NMR for all new compounds, and crystallographic data for 3aa (CCDC 2259037) (PDF)Accession CodesCCDC 2259037 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk

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A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

Wang,

Gong,

Shi

et al. 2024

J. Org. Chem.

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A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3H)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C−H bond thiolation, and nucleophilic cascade cyclization to build the (C−S/C−N) bonds to construct the C−O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.

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A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

Wang,

Gong,

Shi

et al. 2024

J. Org. Chem.

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show abstract

Copper and electrocatalytic synergy for the construction of fused quinazolinones with 2-aminobenzaldehydes and cyclic amines

Shi,

Li,

Wang

et al. 2024

RSC Adv.

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Electrochemical-Induced C–N Bond Formation: A New Method to Synthesis (Z)-Quinazolinone Oximes Using Primary Amines and Quinazolin-4(3H)-one

Cited by 2 publications

References 65 publications

A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

A Multicomponent [2+2+1] Cascade Cyclization to Synthesize Thiazol-2(3H)-one

Copper and electrocatalytic synergy for the construction of fused quinazolinones with 2-aminobenzaldehydes and cyclic amines

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