Solvent-, and Catalyst-free Acylation of Anilines with Meldrum's Acids: ANeat Access to Anilides

Li, Jiang‐Sheng; Da, Yu-Dong; Chen, Guoqin; Yang, Qian; Li, Zhiwei; Yang, Fan; Huang, Peng‐Mian

doi:10.1002/slct.201601965

Cited by 11 publications

(5 citation statements)

References 46 publications

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“…The solvent was removed in vacuo and the product was purified by flash column chromatography (hexane-EtOAc) to give the corresponding tertiary amide. Compounds 3 aa, [14] 3 ba, [15] 3 ca, [16] 3 ha, [17] 3 ja, [18] 3 ka, [19] 3 la, [20] 3 na, [21] 3 ab, [22] 3 ac, [23] 3 ad, [24] 3 ae, [24] 3 af [25] , 3 nf [26] , 3 fa [27] , 3 ga [28] were characterized by comparison of their physical and spectroscopic data with those described in the literature. Full data for the new compounds 3 da, 3 ea and 3 ma are provided below.…”

Section: General Procedures For the Synthesis Of Amides Catalyzed By Cmentioning

confidence: 99%

Amide Bond Formation Catalyzed by Recyclable Copper Nanoparticles Supported on Zeolite Y under Mild Conditions

et al. 2019

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A series of catalysts based on supported copper nanoparticles have been prepared and tested in the amide bond formation from tertiary amines and acid anhydrides, in the presence of tert‐butyl hydroperoxide as an oxidant. Copper nanoparticles on zeolite Y (CuNPs/ZY) was found to be the most efficient catalyst for the synthesis of amides, working in acetonitrile as solvent, under ligand‐ and base‐free conditions in air. The products were obtained in good to excellent yields and in short reaction times. The CuNPs/ZY system also exhibited higher catalytic activity than some commercially available copper and iron sources and it was reused in ten reaction cycles without any further pre‐treatment. This methodology has been successfully scaled‐up to a gram scale with no detriment to the yield.

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Section: General Procedures For the Synthesis Of Amides Catalyzed By Cmentioning

confidence: 99%

Amide Bond Formation Catalyzed by Recyclable Copper Nanoparticles Supported on Zeolite Y under Mild Conditions

et al. 2019

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“…These conditions immediately gave 50% of dichloroacetamide product 3a at room temperature in 16 h (entry 1, Table ), thus supporting our hypothesis that DiCMA ( 2 ) is an effective and reactive dichloroacetylation reagent. While acetylation reactions using alkylated Meldrum’s acid derivatives require elevated reaction temperatures to drive the decarboxylation step, the reaction using 2 proceeds readily at room temperature. This is likely due to the increased electrophilicity of the carbonyl groups and the inability to enolize.…”

mentioning

confidence: 92%

Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent

Heard

Lennox

2021

Org. Lett.

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Dichloromeldrum's acid is introduced as a bench-stable, nonvolatile reagent for the dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO 2 , no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

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“…As an extension of our ongoing research on cholinesterase inhibitors (AChEI), we herein report the dual inhibitor for the acetylcholinesterase and butyrylcholinesterase enzymes. 2,2-Dimethyl-1,3-dioxane-4,6-dione, commonly known as Meldrum's acid, has been named after Andrew Norman Meldrum since 1908 [26]. Initially, the structure of Meldrum's acid (MA) was incorrectly assigned, and after several years Davidson and Bernhard elucidated the correct structure in 1948.…”

Section: Introductionmentioning

confidence: 99%

Dual Inhibition of AChE and BChE with the C-5 Substituted Derivative of Meldrum’s Acid: Synthesis, Structure Elucidation, and Molecular Docking Studies

et al. 2017

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Alzheimer's disease (AD) lies in the category of those diseases which are still posing challenges to medicinal chemists, and the search for super-effective drugs for the treatment of AD is a work in progress. The inhibition of cholinesterase is considered a viable strategy to enhance the level of acetylcholine in the brain. The C-5 substituted derivative of Meldrum's acid was synthesized and screened against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzyme inhibition activity. The simple and unique structure of synthesized derivative 3 was found to be good for the dual inhibition of both enzymes (AChE and BChE). 2,2-Dimethyl-5-(([2-(trifluoromethyl) phenyl]amino)methylidene)-1,3-dioxane-4,6-dione (3) showed significant inhibition against AChE, with an IC 50 value of 1.13 ± 0.03 µ M (Standard Neostigmine 22.2 ± 3.2 µM), and moderate inhibition against BChE, with an IC 50 value of 2.12 ± 1.22 µM (Standard Neostigmine 49.6 ± 6.11 µM). The structural insights reveal that compound 3 possesses intriguing reactive groups, which can potentially evoke the non-covalent interactions and possibly assist by binding in the active site of the target protein. Docking simulations revealed that the compound 3 showed binding inside the active site gorges of both AChE and BChE. An excellent agreement was obtained, as the best docked poses showed important binding features mostly based on interactions due to oxygen atoms and the aromatic moieties of the compound. The docking computations coupled with the experimental findings ascertained that the compound 3 can serve as a scaffold for the dual inhibitors of the human acetylcholine esterases.

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Solvent-, and Catalyst-free Acylation of Anilines with Meldrum's Acids: ANeat Access to Anilides

Cited by 11 publications

References 46 publications

Amide Bond Formation Catalyzed by Recyclable Copper Nanoparticles Supported on Zeolite Y under Mild Conditions

Amide Bond Formation Catalyzed by Recyclable Copper Nanoparticles Supported on Zeolite Y under Mild Conditions

Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent

Dual Inhibition of AChE and BChE with the C-5 Substituted Derivative of Meldrum’s Acid: Synthesis, Structure Elucidation, and Molecular Docking Studies

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