Large-Scale Amidations in Process Chemistry: Practical Considerations for Reagent Selection and Reaction Execution

Organic Process Research & Development, Journal Year: 2022, Volume and Issue: 26(6), P. 1562 - 1689

Published: June 7, 2022

This review describes the practical aspects involved in implementation of large-scale amidations process chemistry. Coupling reagent, base, additive, and solvent selections are critically analyzed to highlight their pros cons. Other important factors be considered on large scale, such as atom economy, cost, safety, toxicity, also examined. These concepts then showcased through selected examples from literature for synthesis active pharmaceutical ingredients.

Language: Английский

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Contemporary Approaches for Amide Bond Formation

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4359 - 4391

Published: Nov. 7, 2023

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

Language: Английский

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Organic Electrosynthesis Towards Sustainability: Fundamentals and Greener Methodologies

The Chemical Record, Journal Year: 2021, Volume and Issue: 21(9), P. 2453 - 2471

Published: May 5, 2021

Abstract The adoption of new measures that preserve our environment, on which survival depends, is a necessity. Electro‐organic processes are sustainable per se , by producing the activation substrate electron transfer at normal pressure and room temperature. In recent years, highly crescent number works organic electrosynthesis available. Novel strategies electrode being developed enabling construction great variety complex molecules. However, possibility scaled‐up mandatory in terms sustainability. Thus, some electrochemical methodologies have demonstrated to report best results reducing pollution saving energy. this personal account, these methods been compiled, organized as follows: • Direct discharge Paired reactions. Organic transformations utilizing electrocatalysis (in absence heavy metals). Selected protocols herein presented discussed with representative examples. Final perspectives reflections also considered.

Language: Английский

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Synthesis, Molecular Docking, and Biological Evaluation of Novel Anthranilic Acid Hybrid and Its Diamides as Antispasmodics

International Journal of Molecular Sciences, Journal Year: 2023, Volume and Issue: 24(18), P. 13855 - 13855

Published: Sept. 8, 2023

The present article focuses on the synthesis and biological evaluation of a novel anthranilic acid hybrid its diamides as antispasmodics. Methods: Due to predicted in silico methods spasmolytic activity, we synthesized molecule 2-(3-chlorophenyl)ethylamine. obtained was then applied acylation with different acyl chlorides. Using analysis, pharmacodynamic profiles compounds were predicted. A thorough conducted assessing their vitro antimicrobial, cytotoxic, anti-inflammatory ex vivo activity. Density functional theory (DFT) calculation, including geometry optimization, molecular electrostatic potential (MEP) surface, HOMO-LUMO analysis for using B3LYP/6-311G(d,p) method explore electronic behavior, reactive regions, stability chemical reactivity compounds. Furthermore, docking simulation along viscosity measurement indicated that newly interact DNA via groove binding mode. results from all experiments demonstrate inherit spasmolytic, capabilities, making them excellent candidates future medications.

Language: Английский

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Novel Anthranilic Acid Hybrids—An Alternative Weapon against Inflammatory Diseases

Pharmaceuticals, Journal Year: 2023, Volume and Issue: 16(12), P. 1660 - 1660

Published: Nov. 29, 2023

Anti-inflammatory drugs are used to relieve pain, fever, and inflammation while protecting the cardiovascular system. However, side effects of currently available medications have limited their usage. Due these adverse effects, there is a significant need for new drugs. The current trend research has shifted towards synthesis novel anthranilic acid hybrids as anti-inflammatory agents. Phenyl- or benzyl-substituted exerted very good in preventing albumin denaturation. To confirm additional ex vivo tests were conducted. These immunohistochemical studies explicated same compounds with better potential. determine binding affinity interaction mode, well explain activities, molecular docking simulation was investigated against human serum albumin. biological evaluation completed, assessing antimicrobial activity spasmolytic effect. Based on experimental data, we can conclude that collection successfully synthesized, they be considered drug candidates-alternatives therapeutics.

Language: Английский

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Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative

Organic Letters, Journal Year: 2021, Volume and Issue: 23(17), P. 6825 - 6830

Published: Aug. 23, 2021

We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by oxidative coupling aromatic or aliphatic aldehydes with amines mediated riboflavin tetraacetate (RFTA), inexpensive organic photocatalyst, visible light using oxygen as sole oxidant. The method is based on power excited flavin catalyst relatively low oxidation potential hemiaminal formed amine to aldehyde addition.

Language: Английский

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Utility of 2-Chloro-N-arylacetamide and 1,1′-(Piperazine-1,4-diyl)bis(2-chloroethanone) as Versatile Precursors for Novel Mono- and Bis[thienopyridines]

ACS Omega, Journal Year: 2024, Volume and Issue: 9(9), P. 10146 - 10159

Published: Feb. 21, 2024

A series of novel thieno[2,3-

Language: Английский

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Recent Advances in Copper‐Catalyzed C−N Bond Formation Involving N‐Centered Radicals

ChemSusChem, Journal Year: 2021, Volume and Issue: 14(24), P. 5340 - 5358

Published: Nov. 9, 2021

Abstract C−N bonds are pervasive throughout organic‐based materials, natural products, pharmaceutical compounds, and agricultural chemicals. Considering the widespread importance of bonds, development greener more convenient ways to form especially in late‐stage synthesis, has become one hottest research goals synthetic chemistry. Copper‐catalyzed radical reactions involving N ‐centered radicals have emerged as a sustainable promising approach build bonds. As chemically popular diverse species, been used for all kinds bond formation by taking advantage their inherently incredible reactive flexibility. Copper is also most abundant economic catalyst with relevant activity facilitating synthesis valuable compounds. Therefore, aim present Review was illustrate recent significant advances methods understand unique advantages copper catalysis generation since 2016. To provide an ease understanding readers, this organized based on types nitrogen sources (amines, amides, sulfonamides, oximes, hydrazones, azides, tert ‐butyl nitrite).

Language: Английский

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Nickel-Catalyzed Electro-Reductive Cross-Coupling of Aliphatic N-Acyl Imides with Alkyl Halides as a Strategy for Dialkyl Ketone Synthesis: Scope and Mechanistic Investigations

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(19), P. 12315 - 12325

Published: Sept. 27, 2022

The development and in-depth study of a cross-electrophile coupling alkyl N-acyl imides with halides relying on the combination nickel catalysis electrochemistry are described. This methodology takes advantages stability simple access as partners for selective synthesis dissymmetric dialkyl ketones. Noteworthy, developed electrochemical protocol affords to linear ketones when using primary bromides featuring different chain lengths. Mechanistic studies including cyclic voltammetry, stoichiometric reactions, isolation catalytic intermediates provide set fundamental insights into monovalent (bpy)nickel-mediated activation imides. Alkyl react electrogenerated (bpy)Ni(I) species via single-electron oxidation give radicals. N-Acyl shown undergo spontaneous C–N bond oxidative addition at both (bpy)Ni(0) species, leading Ni(II) acyl intermediates. A stable nickel(II) complex has also been isolated fully characterized, its competency is demonstrated. Finally, (bpy)Ni(I)–acyl bromide Overall, these investigations allowed comprehensive mechanistic picture this be assembled.

Language: Английский

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Electrosynthesis ofN,N-dimethylformamide from market-surplus trimethylamine coupled with hydrogen production

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(15), P. 5936 - 5944

Published: Jan. 1, 2023

We report an electrochemical oxidation strategy to synthesize DMF directly from market-surplus trimethylamine and couple it with hydrogen production. The reaction was achieved in aqueous medium without any mediator using water as the oxidant.

Language: Английский

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