TiF<sub>4</sub>-catalyzed direct amidation of carboxylic acids and amino acids with amines

Alawaed, Abdulkhaliq A.; Ramachandran, P. Veeraraghavan

doi:10.1039/d3ob01943h

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01943h

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TiF₄-catalyzed direct amidation of carboxylic acids and amino acids with amines

Abdulkhaliq A. Alawaed,

P. Veeraraghavan Ramachandran

Abstract: Unlike other metal fluorides, catalytic titanium tetrafluoride enhances the direct amidation of aromatic and aliphatic carboxylic acids and N-protected amino acids in refluxing toluene. While aromatic acids were converted to...

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Cited by 4 publications

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Recent Advances in Direct Amidation Via Organocatalysis

Hussein,

Hassoon Mageed

2024

Asian J Org Chem

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The formation of amide bonds is essential for a wide range of applications in biological and organic systems, including proteins, pesticides, polymers, and pharmaceuticals. Moreover, it plays a critical role in the synthesis of numerous bioactive compounds with anticancer, antibacterial, and antifungal properties. Due to the limitations of conventional coupling reagents for amide synthesis, there is a growing demand for environmentally sustainable methodologies, particularly the direct formation of amides from carboxylic acids and amines. Over recent years, we have developed several catalytic reactions based on organocatalysis, advancing sustainable synthetic methods in both organic and medicinal chemistry. This review comprehensively discusses catalytic amidation reactions published up to January 2024, focusing on both organocatalysis and boron‐based catalysis for the direct condensation of carboxylic acids and amines. Additionally, it highlights our recent contributions to sustainable amidation protocols, which are progressively replacing traditional catalytic approaches in modern synthetic chemistry.

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Recent Advances in Direct Amidation Via Organocatalysis

Hussein,

Hassoon Mageed

2024

Asian J Org Chem

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Indium‐Catalyzed Direct Amidation Reaction of Carboxylic Acids and In Silico Study for Screening the Activity of Potential Therapeutics of the Synthesized Products

Hussein,

Al‐Jumaili,

Sabi

et al. 2024

ChemistrySelect

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Amide bonds are ubiquitous and valuable motifs in synthetic chemistry, found in a wide range of applications such as the backbone of proteins and pharmaceutical agents. Thus, environmentally friendly and selective methods for synthesizing amide bonds are important. Herein, we report a simple, efficient, and rapid route to access a range of functionalized amides from non‐activated carboxylic acids and amines using indium (III) trifluoromethanesulfonate as an efficient catalyst. A wide range of carboxylic acids – including aliphatic, aromatic, heterocyclic, and dicarbonyl acids – participate smoothly in these reactions, generating structurally diverse amides in moderate to good yields (up to 91 % in 24 examples). The reactions are conducted in dry tetrahydrofuran (THF) under reflux conditions. Furthermore, this amidation strategy provides a method for addressing challenging molecules, such as protected amino acids, to produce biocompatible products. These products can then be used as substrates for various organic transformations, including C−H functionalization reactions. We also demonstrate the synthetic utility of our protocol through the synthesis of essential substrates in organic and medicinal chemistry by reacting N‐protected carboxylic acids with 8‐aminoquinoline to produce a series of biologically valuable compounds. Five of these products, named 4 f, 4p, 9a, 9c, and 9d, have been biologically evaluated through an in‐silico study. The interaction of these compounds with receptor protein 8DQT was examined to assess their potential as drug candidates for hypertension treatment. Effective binding was detected between these compounds and the receptor. Data from molecular docking studies show that compounds 4d and 4 m are the most active, with binding scores of −8.8 and −8.6 kcal/mol, respectively. However, compound 4 m exhibited a stronger binding affinity than compound 4d over the course of dynamic simulation. Our ADMET study suggests that all five compounds are highly safe in the body. Based on the BOILED‐Egg model study, good absorption is suggested for all the molecules, and they can cross the blood‐brain barrier.

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Potassium hexafluorotitanate as a catalytic activator for direct amidation of carboxylic acids

Singh,

Ramachandran

2024

Journal of Fluorine Chemistry

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TiF₄-catalyzed direct amidation of carboxylic acids and amino acids with amines

Abstract: Unlike other metal fluorides, catalytic titanium tetrafluoride enhances the direct amidation of aromatic and aliphatic carboxylic acids and N-protected amino acids in refluxing toluene. While aromatic acids were converted to...

Cited by 4 publications

References 44 publications

Recent Advances in Direct Amidation Via Organocatalysis

Recent Advances in Direct Amidation Via Organocatalysis

Indium‐Catalyzed Direct Amidation Reaction of Carboxylic Acids and In Silico Study for Screening the Activity of Potential Therapeutics of the Synthesized Products

Potassium hexafluorotitanate as a catalytic activator for direct amidation of carboxylic acids

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TiF4-catalyzed direct amidation of carboxylic acids and amino acids with amines

Abstract: Unlike other metal fluorides, catalytic titanium tetrafluoride enhances the direct amidation of aromatic and aliphatic carboxylic acids and N-protected amino acids in refluxing toluene. While aromatic acids were converted to...

Cited by 4 publications

References 44 publications

Recent Advances in Direct Amidation Via Organocatalysis

Recent Advances in Direct Amidation Via Organocatalysis

Indium‐Catalyzed Direct Amidation Reaction of Carboxylic Acids and In Silico Study for Screening the Activity of Potential Therapeutics of the Synthesized Products

Potassium hexafluorotitanate as a catalytic activator for direct amidation of carboxylic acids

Contact Info

Product

Resources

About

TiF₄-catalyzed direct amidation of carboxylic acids and amino acids with amines