Base-promoted triple cleavage of CCl<sub>2</sub>Br: a direct one-pot synthesis of unsymmetrical oxalamide derivatives

Jayaram, Alageswaran; Seenivasan, Vijay Thavasianandam; Govindan, Karthick; Liu, Yu-Ming; Chen, Nian-Qi; Yeh, Ting-Wei; Venkatachalam, Gokulakannan; Li, Chien-Hung; Leung, Tsz-Fai; Lin, Wei-Yu

doi:10.1039/d4cc00354c

Chem. Commun.

2024

DOI: 10.1039/d4cc00354c

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Base-promoted triple cleavage of CCl₂Br: a direct one-pot synthesis of unsymmetrical oxalamide derivatives

Alageswaran Jayaram,

Vijay Thavasianandam Seenivasan,

Karthick Govindan

et al.

Abstract: We present a novel, eco-friendly and one-pot approach for synthesizing unsymmetrical oxalamide with the aid of dichloroacetamide and amine/amides in the presence of CBr4 under a basic medium. The use...

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Cited by 3 publications

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Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Govindan,

Jayaram,

Seenivasan

et al. 2024

ChemCatChem

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Nitrogen‐containing heterocycles represent fundamental components found in a myriad of natural compounds, pharmaceuticals, tailored bioactive substances, and agrochemicals. In recent decades, the field of synthetic chemistry has prioritized these compounds, directing considerable research endeavour toward developing efficient and concise methodologies for their synthesis. Consequently, there is a growing interest in pioneering novel synthetic approaches to fabricate these immensely coveted structural motifs. Transition metal‐catalyzed reactions leveraging solvents as carbon (C1) synthons offer notable advantages, including streamlined processes, enhanced atom economy, and environmental sustainability. This review sheds light on the recent advancements in the utilization of collective solvents such as methanol (alongside other alcohols), N,N‐dimethylethanolamine (DMEA), and triethylamine (TEA) (in conjunction with other amines), tetrahydrofuran (THF), toluene, dichloromethane (DCM), dimethyl sulfoxide (DMSO), and dimethylformamide (DMF) as C1 synthons, serving as foundational units for the synthesis of N‐heterocycles, including quinazolinone, quinazoline, quinoxaline, pyridine, and pyrimidine, among others. Various reaction conditions employing diverse transition metals, coupling partners, and solvents as carbon synthons or reagents, as reported in the literature, have been explored.

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Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Govindan,

Jayaram,

Seenivasan

et al. 2024

ChemCatChem

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Mechanism and optimization of ruthenium-catalyzed oxalamide synthesis using DFT

Monreal-Corona,

Joly,

Gaillard

et al. 2025

Dalton Trans.

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TBN-promoted regioselective C–C bond cleavage: a new strategy for the synthesis of unsymmetrically substituted N-aryl oxalamides

Liu,

Zhang,

Wang

et al. 2025

Org. Chem. Front.

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Base-promoted triple cleavage of CCl₂Br: a direct one-pot synthesis of unsymmetrical oxalamide derivatives

Abstract: We present a novel, eco-friendly and one-pot approach for synthesizing unsymmetrical oxalamide with the aid of dichloroacetamide and amine/amides in the presence of CBr4 under a basic medium. The use...

Cited by 3 publications

References 39 publications

Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Mechanism and optimization of ruthenium-catalyzed oxalamide synthesis using DFT

TBN-promoted regioselective C–C bond cleavage: a new strategy for the synthesis of unsymmetrically substituted N-aryl oxalamides

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Base-promoted triple cleavage of CCl2Br: a direct one-pot synthesis of unsymmetrical oxalamide derivatives

Abstract: We present a novel, eco-friendly and one-pot approach for synthesizing unsymmetrical oxalamide with the aid of dichloroacetamide and amine/amides in the presence of CBr4 under a basic medium. The use...

Cited by 3 publications

References 39 publications

Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Transition‐Metal Catalyzed Synthesis of N‐Heterocycles using Solvent‐Carbon (C1) Synthons

Mechanism and optimization of ruthenium-catalyzed oxalamide synthesis using DFT

TBN-promoted regioselective C–C bond cleavage: a new strategy for the synthesis of unsymmetrically substituted N-aryl oxalamides

Contact Info

Product

Resources

About

Base-promoted triple cleavage of CCl₂Br: a direct one-pot synthesis of unsymmetrical oxalamide derivatives