Efficient Synthesis of N‐Acylureas Using Copper Oxide Supported on Magnetic Nanoparticles in Deep Eutectic Solvent

Abbasi, Sepideh; Miraki, Maryam Kazemi; Radfar, Iman; Karimi, Meghdad; Heydari, Akbar

doi:10.1002/slct.201702315

Cited by 9 publications

(7 citation statements)

References 28 publications

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“…The elemental analysis, IR, and NMR techniques were used to investigate the structure of the newly synthesized compounds. 13 7.95 (dd, J 1 = 6.6 Hz, J 2 = 1.5 Hz, 1H), 7.75 (d, J = 6 Hz, 2H), 7.6 (t, 1H), 5.54 (s, 1H), 4.5 (m, 1H) 3.5 (m, 1H), 1.9−0.55 (m, 20H). 13 C NMR (100 MHz, CDCl 3 ) δ: 167.5, 156.3, 148.9, 147.8, 137.5, 136.2, 132.9, 130.5, 126, 124.4, 52, 49.8, 33.6, 31.5, 25.9, 24.82, 24.79, 24.7.…”

Section: Procedures For the Synthesis Of 1-(4-(4-methylphenyl)benzoyl...mentioning

confidence: 99%

“…6 Abbasi and colleagues recently described a green magnetic nanocatalyst reaction of carbodiimides with carboxylic acid to produce Nacyl urea. 7 Compounds containing a biaryl linkage have various applications in pharmaceutical and material sciences. 8 Prep-aration of novel compounds, when achieved using palladiumcatalyzed Suzuki−Miyaura cross-coupling (SMC) of aryl halides with arylboronic acids, is both exceptionally versatile and remarkably expedient since boronic acids are usually nontoxic, chemically inert to air and moisture, and thermally stable and are far easier to handle than other frequently used cross-coupling reagents.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 1-(4-Bromobenzoyl)-1,3-dicyclohexylurea and Its Arylation via Readily Available Palladium Catalyst─Their Electronic, Spectroscopic, and Nonlinear Optical Studies via a Computational Approach

Maqbool,

Younas,

Bilal

et al. 2023

ACS Omega

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In this study, we reported the synthesis of 1-(4bromobenzoyl)-1,3-dicyclohexylurea by the reaction of DCC (N,N′-dicyclohexylcarbodiimide) with 4-bromobenzoic acid. Subsequently, we further synthesized a new series of 1-(4-arylbenzoyl)-1,3-dicyclohexylurea (5a−g) derivatives using a Suzuki crosscoupling reaction between 1-(4-bromobenzoyl)-1,3-dicyclohexylurea (3) and various aryl/heteroaryl boronic acids (4). Thus, density functional theory (DFT) calculations have been performed to examine the electronic structure of the synthesized compounds (3, 5a−g) and to calculate their spectroscopic data. Moreover, optimized geometries and thermodynamic properties, such as frontier molecular orbitals (HOMO, LUMO), molecular electrostatic potential surfaces, and reactivity descriptors, were also calculated at the PBE0-D3BJ/def2-TZVP/SMD 1,4-dioxane level of theory to validate the structures of the synthesized compounds.

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Section: Procedures For the Synthesis Of 1-(4-(4-methylphenyl)benzoyl...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-(4-Bromobenzoyl)-1,3-dicyclohexylurea and Its Arylation via Readily Available Palladium Catalyst─Their Electronic, Spectroscopic, and Nonlinear Optical Studies via a Computational Approach

Maqbool,

Younas,

Bilal

et al. 2023

ACS Omega

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“…Finally, N-acylureas were prepared using N,N′-dicyclohexylcarbodiimide (DCC) and benzoic acid derivatives at 60 °C in the mixture ChCl:urea (1:2) as a solvent. This reaction was catalyzed by copper oxide supported in magnetic iron nanoparticles [ 124 ].…”

Section: Miscellaneousmentioning

confidence: 99%

Deep Eutectic Solvents as à-la-Carte Medium for Transition-Metal-Catalyzed Organic Processes

Marset

Guillena

2022

Molecules

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Our society is facing a tremendous challenge to become more sustainable in every sphere of life. Regarding the chemical industry, one of the most significant issues to be addressed is the use of volatile organic compounds (VOCs) as solvents because they are petrol-derived and most of them are toxic and flammable. Among the possible solutions, deep eutectic solvents (DESs) have emerged as sustainable alternatives to VOCs in organic catalyzed transformations and other fields. The advantages of these new reaction media are not only related to their more benign physical and chemical properties and, for most of them, their renewable sources but also due to the possibility of being recycled after their use, increasing the sustainability of the catalyzed process in which they are involved. However, their use as media in catalytic transformations introduces new challenges regarding the compatibility and activity of known catalysts. Therefore, designed catalysts and “à-la-carte” DESs systems have been developed to overcome this problem, to maximize the reaction outcomes and to allow the recyclability of the catalyst/media system. Over the last decade, the popularity of these solvents has steadily increased, with several examples of efficient metal-catalyzed organic transformations, showing the efficiency of the catalysts/DES system, compared to the related transformations carried out in VOCs. Additionally, due to the inherent properties of the DES, unknown transformations can be carried out using the appropriated catalyst/DES system. All these examples of sustainable catalytic processes are compiled in this review.

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“…[5] A recent method has reported the preparation of N-acylureas using dicyclohexylcarbodiimide (DCC) and various carboxylic acids using a copper-oxide nanocatalyst, but the urea -substituted alkyl side chains were only limited to the cyclohexyl group (Scheme 1b). [6] Interestingly, acyl carbamates are useful intermediates and can react with amines to produce N-acylureas (Scheme 1c). Here the acyl carbamates are prepared from diphenyl carbonate and sodium hydride.…”

Section: Introductionmentioning

confidence: 99%

A new and facile synthesis of N-benzyl-N′-acylureas via reaction of dibenzoylhydrazine carboxamide and benzylamines

Valipour

Chippindale

Kouzeli

et al. 2021

Synthetic Communications

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Herein, we report a new method of synthesis of N-acylureas (E1-5) via reaction of dibenzoylhydrazine carboxamide (N,2-bis(4-methoxybenzoyl)hydrazine-1-carboxamide) (C) and various benzylamines. Preparation of dibenzoylhydrazine carboxamide was performed by the treatment of 5,6-diaryl-3-methylthio-1,2,4-triazine (B) with Oxone which leads to oxidation and triazine ring cleavage in high yield (82%). Five benzylamine derivatives containing different electron donating and withdrawing substituents were used in this study. Yields for the conversion of dibenzoylhydrazine carboxamide (C) to N-acylureas (E1-5) were in the range of 40-55%. The structures of the intermediates and final products were characterized and confirmed by NMR, mass spectrometry and single-crystal X-ray crystallography.

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Efficient Synthesis of N‐Acylureas Using Copper Oxide Supported on Magnetic Nanoparticles in Deep Eutectic Solvent

Cited by 9 publications

References 28 publications

Synthesis of 1-(4-Bromobenzoyl)-1,3-dicyclohexylurea and Its Arylation via Readily Available Palladium Catalyst─Their Electronic, Spectroscopic, and Nonlinear Optical Studies via a Computational Approach

Synthesis of 1-(4-Bromobenzoyl)-1,3-dicyclohexylurea and Its Arylation via Readily Available Palladium Catalyst─Their Electronic, Spectroscopic, and Nonlinear Optical Studies via a Computational Approach

Deep Eutectic Solvents as à-la-Carte Medium for Transition-Metal-Catalyzed Organic Processes

A new and facile synthesis of N-benzyl-N′-acylureas via reaction of dibenzoylhydrazine carboxamide and benzylamines

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