Transamidation of aromatic amines with formamides using cyclic dihydrogen tetrametaphosphate

Chouhan, Kishor Kumar; Chowdhury, Deep; Mukherjee, Arup

doi:10.1039/d2ob00882c

Cited by 8 publications

(5 citation statements)

References 101 publications

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“…[130] The utilization of stoichiometric promoters continues to be an area of ongoing exploration, exemplified by Song and Lee [131] employing TMSCl as the coupling promoter, and by Mukherjee employing dihydrogen tetrametaphosphate. [132] Finally, one of the most inspiring recent instances of transamidation involving non-activated amides was achieved by Szostak and Chen. [133] They employed TfOH as the electrophilic activator of the amide [134] and KI to generate an acyl iodide in-situ.…”

Section: Amidesmentioning

confidence: 99%

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Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out of the thirty‐seven new drugs approved by the FDA in 2022, eleven are small molecules containing at least one amide bond. Additionally, there are nineteen large molecules approved as new drugs, some of which have peptide structures, and therefore, also bear amide bonds. In recent years, multiple teams have embraced the challenge of developing more efficient methods for amide bond formation. This dedication has led to numerous publications appearing monthly in prestigious journals, showcasing significant advancements in this field. The primary goal of this review is to present the most viable strategies for constructing the amide bond. It is crucial to differentiate between amide bond formation and amide synthesis; hence, the focus is on describing specific methods for forming new C(O)−N bonds. In particular, this review concentrates on the methods developed within the last six years. There is a particular emphasis on new approaches that consider the thought process when selecting the starting materials and functional groups. This approach ensures coverage of all the most common chemical transformations that yield new amide bonds.

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Section: Amidesmentioning

confidence: 99%

“…The utilization of stoichiometric promoters continues to be an area of ongoing exploration, exemplified by Song and Lee [131] employing TMSCl as the coupling promoter, and by Mukherjee employing dihydrogen tetrametaphosphate [132] …”

Section: Amides From Carbonyl‐containing Compoundsmentioning

confidence: 99%

Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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“…The authors have cited additional references within the Supporting Information. [10][11][12][13][14][15][16][17][18][19][20][21]…”

Section: Supporting Informationmentioning

confidence: 99%

Dual Role of TiO(acac)₂ as a Reagent and an Activator/Catalyst: A Study on the Solvent Dependent Product Formation

Kumar Chouhan,

Nad,

Mukherjee

2023

Chemistry An Asian Journal

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The dual operation of a chemical species in synthetic chemistry is an intriguing and relatively unexplored phenomenon. The application of such a species is expected to reduce the use of multiple reaction partners and catalysts/activators. Herein, we report a simple and easy‐to‐use protocol for the twin application of TiO(acac)2, as a reagent and an activator to synthesize β‐enamino ketones with amines in acetonitrile. The same early transition metal precursor when employed in N,N‐dimethylformamide with the amines, resulted in the formation of the substituted amides. Both reactions were explored with various substrates to check the viability of the present protocol. Moreover, experimental studies were conducted to understand the mechanism of both reactions.

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“…[4][5][6] The presence of carboxamide functional groups within diverse compounds facilitates the prevention and treatment of numerous health disorders. [7][8][9] Some drugs are shown in Fig. 1.…”

Section: Introductionmentioning

confidence: 99%

Transamidation of secondary carboxamides and amidation of esters are facilitated by magnetic Co@NC nanoparticles, as a highly efficient and recyclable catalyst under neat conditions

Singh,

Rajput,

Mahaur

et al. 2024

New J. Chem.

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Transamidation of aromatic amines with formamides using cyclic dihydrogen tetrametaphosphate

Abstract: Amide fragments are found to be one of the key constituents in a wide range of natural products and pharmacologically active compounds. Herein, we report a simple and efficient protocol...

Cited by 8 publications

References 101 publications

Contemporary Approaches for Amide Bond Formation

Contemporary Approaches for Amide Bond Formation

Dual Role of TiO(acac)₂ as a Reagent and an Activator/Catalyst: A Study on the Solvent Dependent Product Formation

Transamidation of secondary carboxamides and amidation of esters are facilitated by magnetic Co@NC nanoparticles, as a highly efficient and recyclable catalyst under neat conditions

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Transamidation of aromatic amines with formamides using cyclic dihydrogen tetrametaphosphate

Abstract: Amide fragments are found to be one of the key constituents in a wide range of natural products and pharmacologically active compounds. Herein, we report a simple and efficient protocol...

Cited by 8 publications

References 101 publications

Contemporary Approaches for Amide Bond Formation

Contemporary Approaches for Amide Bond Formation

Dual Role of TiO(acac)2 as a Reagent and an Activator/Catalyst: A Study on the Solvent Dependent Product Formation

Transamidation of secondary carboxamides and amidation of esters are facilitated by magnetic Co@NC nanoparticles, as a highly efficient and recyclable catalyst under neat conditions

Contact Info

Product

Resources

About

Dual Role of TiO(acac)₂ as a Reagent and an Activator/Catalyst: A Study on the Solvent Dependent Product Formation