Repurposing n-butyl stannoic acid as highly efficient catalyst for direct amidation of carboxylic acids with amines

Potadar, Santoshkumar M.; Mali, Anil S.; Waghmode, Krishnakant T.; Chaturbhuj, Ganesh U.

doi:10.1016/j.tetlet.2018.11.036

Cited by 10 publications

(4 citation statements)

References 62 publications

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“…Amides production is one of the most essential processes of the pharmaceutical and chemical industries . These types of molecules are extensively utilized as building blocks in the preparation of pharmaceuticals, pigments, agrochemicals, photographic products, and polymers. − About 30% of drug molecules have at least one amide linked, demonstrating its relevance in drug design and the pharmaceutical industry …”

Section: Introductionmentioning

confidence: 99%

“…A plethora of synthetic methodologies to access amide functionalities have been improved or developed. − Conventional methods involve the nucleophilic substitution of amines on carboxyl groups. However, the hydroxyl group is not a good leaving group, and for this reason, it is necessary to employ activated carboxylic acid derivatives including anhydrides, acyl chlorides, or stoichiometric amounts of condensation reagents, which generates large amounts of unwanted secondary products . The direct catalytic formation of amides from carboxylic acids and amines is a highly desirable greener route.…”

Section: Introductionmentioning

confidence: 99%

“…2−4 About 30% of drug molecules have at least one amide linked, demonstrating its relevance in drug design and the pharmaceutical industry. 5 A plethora of synthetic methodologies to access amide functionalities have been improved or developed. 6−9 Conventional methods involve the nucleophilic substitution of amines on carboxyl groups.…”

Section: ■ Introductionmentioning

confidence: 99%

“…However, the hydroxyl group is not a good leaving group, and for this reason, it is necessary to employ activated carboxylic acid derivatives including anhydrides, acyl chlorides, or stoichiometric amounts of condensation reagents, which generates large amounts of unwanted secondary products. 5 The direct catalytic formation of amides from carboxylic acids and amines is a highly desirable greener route. The most relevant method involves thermal activation of carboxylic acids and amines using polar solvents 10 and molecular sieves 11 or largely increasing the reaction temperature, which displaces the equilibrium and favors the release of water formed.…”

Section: ■ Introductionmentioning

confidence: 99%

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Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Chaparro

Rojas

Castillo

et al. 2020

ACS Sustainable Chem. Eng.

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Biogenic carbonates were studied as catalysts in this work for the direct synthesis of amides under solvent-free conditions. Solids were synthesized by microbial coprecipitation of CaCl 2 and Ni salts and Cu and Fe salts. The catalysts were characterized by thermogravimetric analysis, nitrogen physisorption measurements, X-ray diffraction, and X-ray photoelectron spectroscopy. The polymorphism, hydrophilicity, and textural properties depended on the metal oxides type incorporated on CaCO 3 . N-Arylsuccinimides synthesis was employed as test reaction, obtaining remarkable selectivity and conversion in the reaction of succinic acid with p-toluidine and aniline, respectively. Optimized conditions were subsequently extended to the solvent-free synthesis of diverse amides in good yields using CuO−CaCO 3 as the catalyst in air. The direct amidation protocol was amenable to the use of different primary amines and nonactivated carboxylic acids.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Solventless Amide Synthesis Catalyzed by Biogenic CaCO₃ Materials

Chaparro

Rojas

Castillo

et al. 2020

ACS Sustainable Chem. Eng.

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Exploring Structural and Spectroscopic Properties of Secondary Amide Derivatives Bearing Bulky and Hydrophilic Substituents

Nossa González,

Gómez Castaño,

Franca

et al. 2023

ChemistrySelect

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The synthesis of four novel amide compounds (R1C(O)NHR2) is reported, which contain both bulky (R1=phenyl and adamantyl) and hydrophilic (R2=hydroxyl, methoxyl) groups. The incorporation of such substituents provides compounds with unique properties that combine steric hindrance and hydrophilicity. The synthesized amides were fully characterized by 1H and 13C nuclear magnetic resonance (NMR) and analysed using infrared (IR) and Raman spectroscopy to investigate their vibrational properties in the solid phase, specifically focusing on the amide‐type normal modes of vibrations. Furthermore, the crystal structures of three derivatives were determined by single‐crystal X‐ray diffraction, which provided insights into their molecular arrangements. The occurrence of N−H⋅⋅⋅O=C hydrogen bonding intermolecular interaction is clearly observed and characterized by Hirschfeld surface analysis. Topology analysis using the Quantum Theory of Atom in Molecules and Crystals (QTAIM−C) were employed to investigate the electronic properties of the isolated amide molecules and to analyse the intermolecular interactions within the crystalline structure. The periodic calculations for the crystal revealed a higher electronic density in the C−N bond, indicating an increased covalent character in this bond compared with the C=O bond. This observation indicates the presence of resonance‐assisted hydrogen bonds within the amide core, leading to π electronic delocalization.

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