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Tetrahedron Letters
Volume 56, Issue 24,
10 June 2015
, Pages 3799-3803
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Abstract
Dimethylacetamide (DMAc) acts as an efficient source of acetyl and dimethylamine gas in the presence of N,N-carbonyldiimidazole (CDI). Addition of amines to the reaction mixture delivers the corresponding amides in good to excellent yields. The acetylation of amines reported herein, which relies on the in situ generation of N-acetylimidazole on warming of DMAc with CDI at 120–125°C, serves as a convenient alternative to other acetylation methods.
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Acknowledgments
We thank Sudhir Nambiar, R. Sridharan, Ramachandra Puranik, and Bill Moss for useful discussions in the manuscript preparation.
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KO<sup>t</sup>Bu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines
2019, Organic Letters
This work discloses transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.
Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines
2019, Organic Letters
A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.
Cobalt(II)-Catalyzed N-Acylation of Amines through a Transamidation Reaction
2018, European Journal of Organic Chemistry
A practical protocol has been developed for a Co(OAc)24H2O‐catalyzed transamidation reaction. The reaction gives high yields and uses N,N‐dimethylformamide and other amides as carbonyl sources. The protocol is rapid and simple, and it does not require any acids, bases, ligands, or other additives. It works well for a wide range of primary, secondary, and heterocyclic amines.
Sulfonated graphene oxide-catalyzed N-acetylation of amines with acetonitrile under sonication
2018, Journal of the Taiwan Institute of Chemical Engineers
Citation Excerpt :
The formed amide molecules can be further utilized in wide industrial applications such as pharmaceuticals, agrochemicals, and polymers [4–5]. For amide formation, N-acetylation is usually conducted by the reaction of amines with carboxylic acid derivatives, e.g. acetic anhydride, acetyl halides, and esters [6–9]. Nevertheless, a number of inherited problems have been encountered in N-acetylation [10]: Acyl halides and anhydrides are moisture sensitive and readily reacted with water and alcohols to form the corresponding acids and esters, which leads to the low purity in desired amides [11-15]; The reagents mentioned above are banned in several countries because they could also be used in the synthesis of narcotics; The reactants mostly need basic media like imidazole and pyridine to carry out the reaction [16,17]; The base catalysts are well known for their toxic properties to the environment and humans.
Sulfonated reduced graphene oxide (rGO-SO3H, SRGO) was synthesized by introducing aryl diazonium salt of sulfanilic acid radicals onto chemically modified reduced graphene oxide (rGO) under sonication. SRGO catalyst was characterized by X-ray diffraction (XRD), Raman spectroscopy, solid state 13C MAS NMR (13C SSNMR), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), transmission electron spectroscopy (TEM), and X-ray photoelectron spectroscopy (XPS). SRGO was efficiently used as a reusable, metal-free, solid acid catalyst for the direct N-acetylation of amines with acetonitrile under sonication into the corresponding amides. Thus, the method could also serve as a novel convenient alternative for the other acetylation reactions under sonication to avoid using toxic substances such as acetic anhydride, acetyl chloride, and acetic acid.
Cu(II) coordination polymers constructed by tetrafluoroterephthalic acid and varied imidazole-containing ligands: Syntheses, structures and properties
2018, Journal of Solid State Chemistry
Citation Excerpt :
Blue crystals of 2 were isolated after washed with acetone, and dried in the air. Note that 2 was prepared through an in situ ligand reaction in which N,N’-carbonyldiimidazole(cdi) broke up into imidazole ligand [58,59]. Yield: 52%.
Six new copper(II) coordination polymers combining 2,3,5,6-tetrafluoroterephthalatic acid (H2tfBDC) and diverse imidazole-containing ligands, {[Cu(tfBDC)(1,2-bix)2]·2(H2O)}n (1), {Cu(tfBDC)(Im)2}n (2), {[Cu(1,4-bmimb)2(H2O)]·(tfBDC)·2(H2O)}n (3), {Cu(1,4-bimb)2(H2O)2·(tfBDC)}n (4), {[Cu(1,3-bix)2(H2O)2]·(tfBDC)·6(H2O)}n (5) and {[Cu(1,4-bix)2(H2O)2]·(tfBDC)·(1,4-bix)·4(H2O)}n (6) (1,2-bix = 1,2-bis(imidazole-1-ylmethyl)-benzene, Im = imidazole, 1,4-bmimb = 1,4-bis((2-methyl-1H-imidazol-1-yl)methyl)benzene, 1,4-bimb = 1,4-bis(imidazol-1-yl)-butane, 1,3-bix = 1,3-bis(imidazole-1-ylmethyl)-benzene, 1,4-bix = 1,4-bis(imidazole-1-ylmethyl)-benzene), have been obtained and structurally verified by single-crystal X-ray diffraction analyses and further characterized by powder X-ray diffraction (PXRD), elemental analyses and infrared spectroscopy (IR). Single crystal X-ray diffraction analysis revealed that 1 is 2D 4-connected sql topology (point symbol: {44·62}) based on a single metal ion node. Compound 2 is characterized as an infinite 1D chain structure, which is further extended into a 2D layer through N-H···O hydrogen bonds and then a 3D supramolecular architecture via π···π stacking interactions. Note that 2 was prepared through an in situ ligand reaction in which N,N’-carbonyldiimidazole (cdi) broke up into imidazole ligand. Compound 3 possesses a 3D 4-fold interpenetrated architecture with 4-connected dia topology (Schläfli symbol: {66}) in which tfBDC2- is stabilized in the channel by hydrogen bonds. Compounds 4–6 are all linear 1D coordination polymers. In 4, the free tfBDC2- ligand acts as a μ4-bridge to link four coordinated water molecules from the chain to construct a 2D structure via hydrogen bonds. While in 5 and 6, the uncoordinated tfBDC2- ligands and multimeric water clusters is responsible for the conversion of these 1D coordination polymers into 3D supramolecular assemblies through O–H⋯O hydrogen bonding interactions. Moreover, the UV–vis spectra and thermal stability of 1–6 are discussed in detail.
Selective N-acetylation of aromatic amines using acetonitrile as acylating agent
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A method for N-acetylation of amines has been developed using acetonitrile as an acylating agent and in situ generated trimethylsilyl iodide as the catalyst under microwave heating condition. The reaction is selective toward aromatic amines while aliphatic amines remain intact. The process eliminates the requirement of toxic acylating reagents like acetic anhydride and acetyl chloride.
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Copyright © 2015 Elsevier Ltd. All rights reserved.
FAQs
What is the acetylation reaction of amines? ›
N-acetylation is a widely used chemical reaction in general organic chemistry to build an acetyl functional group on an amine compound [1,2,3,4].
How can you carry out the acetylation of aromatic amines? ›A method for N-acetylation of amines has been developed using acetonitrile as an acylating agent and in situ generated trimethylsilyl iodide as the catalyst under microwave heating condition. The reaction is selective toward aromatic amines while aliphatic amines remain intact.
What is the N-acetylation using acetyl chloride? ›N-acetylation of anilines with acetyl chloride leads to the production of one equivalent acid, which will form salt with unreacted aniline. The addition of an equivalent of base like K2CO3 neutralises the liberated acid and catalytic amount of PTC leads to achieve high yields in shorter period.
What is acetylation of aniline? ›Acetylation of aniline gives acetanilide, which undergoes nitration at low temperature, yielding the para-nitro product in high yield. The modifying acetyl group can then be removed by acid-catalyzed hydrolysis, to yield para-nitroaniline.
What is the purpose of acetylation of amines? ›Acetylation is often used to place an acetyl protecting group on primary or secondary amines to reduce their reactivity toward oxidizing agents or electrophiles. Acetamides are usually crystalline solids which can be a help in purification by recrystallization.
Why does acetylation of amine reduce its activation effect? ›Acetylation of −NH2 group of aniline reduces its activating effect because the lone pair on the nitrogen atom is in conjugation with the carbonyl group in acetylated aniline.
Which reagent can be utilized in acetylation reaction? ›Acetylation reagents
Acetic anhydride. This reagent is common in the laboratory; its use cogenerates acetic acid. Acetyl chloride. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable.
Tertiary amine does not undergo acylation reaction.
What is the solvent for acetylation reaction? ›Acetylation reactions are classically performed using excess of acetic anhydride (Ac2O) in solvent-free conditions or by eventually working with stoichiometric amounts of Ac2O in organic solvents; both methods require the addition of basic or acid catalysts to promote the esterification.
What are the 2 types of acetylation? ›Acetylation occurs mainly on lysine and can be divided into histone acetylation and non-histone protein acetylation (7).
What is the importance of acetylation reaction? ›
Proteins that replicate DNA and repair damaged genetic material are created directly by acetylation. Acetylation also helps in DNA transcription. Acetylation determines the energy that proteins use during duplication and this determines the accuracy of copying the genes.
What does N acetylated mean? ›N-terminal acetylation (Nt-acetylation) is a widespread protein modification among eukaryotes and prokaryotes alike. By appending an acetyl group to the N-terminal amino group, the charge, hydrophobicity, and size of the N-terminus is altered in an irreversible manner.
Why is acetylation of aniline necessary? ›The acetyl group that later gets attached with aniline deactivates the aniline due to its electron withdrawing tendency. Thus, we will say that acetylation of aniline reduces its activation effect.
Does acetylation affect DNA? ›Acetylation usually occurs on lysine residues, neutralizing their positive charge and thereby causing histones to drift away from DNA, which has a negative charge. The released structure facilitates access to transcriptional machinery such as transcription factors and RNA polymerase II.
What does acetylation do to amino acids? ›Acetylation affects many protein functions, including enzymatic activity, stability, DNA binding, protein-protein interaction, and peptide-receptor recognition, and occurs on numerous and diverse proteins.
What is the role of acetic acid in acetylation? ›Acylation is an effective C-C bond-forming reaction to condense acetic acid and lignin-derived aromatic compounds into acetophenones, valuable precursors to fuels and chemicals. However, acetic acid is intrinsically an ineffective acylating agent.
Does acetylation need a catalyst? ›Acetylation reactions are classically performed using excess of acetic anhydride (Ac2O) in solvent-free conditions or by eventually working with stoichiometric amounts of Ac2O in organic solvents; both methods require the addition of basic or acid catalysts to promote the esterification.
What is the purpose to adding acetyl groups? ›The addition of the acetyl group neutralizes this positive charge and hence reduces the binding between histones and DNA, leading to a more open structure which is more accessible to the transcriptional machinery.
What are the consequences of acetylation? ›Acetylation of lysines can alter the three-dimensional structure of a protein, affecting its ability to bind other proteins or DNA. Furthermore, acetylation can have an impact on the subcellular localization, activity, and stability of a protein.
Does acetylation increase protein activity? ›Acetylation is a modification that can dramatically change the function of a protein through alteration of its properties, including hydrophobicity, solubility, and surface properties, all of which may influence protein conformation and interactions with substrates, cofactors and other macromolecules.
Does acetylation tighten or loosen DNA? ›
Acetylation and Deacetylation
The addition of the acetyl group lowers the positive charge on the histone and loosens its binding to the negatively charged DNA. Acetylation of histones therefore results in activation of gene transcription.
Reaction of acetylation of salicylic acid
Here, salicylic acid is subjected to acetylation with the help of acetic anhydride to yield acetylsalicylic acid (commonly known as aspirin) and acetic acid as the final product.
ACSS enzymes catalyze ATP-dependent ligations of acetate and CoA to produce acetyl-CoA.
Which compound is widely used as acetylating agent? ›Acetic anhydride is used.
Which drugs undergo N acetylation? ›Acetylation is an important route of metabolism and elimination for a large number of clinically important drugs, including isoniazid, dapsone, procainamide, sulfonamides, hydralazine, and phenelzine.
Does acetylation inhibit? ›Acetylation of lysine residues on the histone tails is directly involved in regulation of gene transcription. Already in 1964, it was shown that histone binding to DNA-inhibited gene transcription. In addition, it was shown that chemical acetylation of histones could reduce this inhibiting effect [6].
What are examples of drugs that undergo acetylation? ›Many common drugs such as caffeine, isoniazid, nitrazepam and sulphonamides are acetylated.
What is the mechanism of action of acetylation? ›Acetylation neutralizes the positively charged lysines and therefore affects interactions of the histones with other proteins and/or with DNA. Histone acetylation has long been associated with transcriptionally active chromatin and also implicated in histone deposition during DNA replication (1, 2).
Why are drugs acetylated? ›The function of acetylation may be to deactivate the drug, although N-acetylprocainamide is as potent as the parent antiarrhythmic drug procainamide (Procanbid).
What are the end products of acetylation? ›Salicylic acid reaction of Acetylation:
Acetic anhydride is used to acetylate salicylic acid, yielding acetylsalicylic (aspirin) and acetic acid as end products.
What are the two most common acetylating agents? ›
Two of the most common acylating reagents used in organic chemistry are acetic anhydride and acyl chloride.
What is the difference between acylation and acetylation reaction? ›Differences between Acetylation and Acylation
The addition of an acetyl group to a molecule is known as acetylation. Acylation is a chemical reaction in which an acyl group is added to a chemical molecule.
For instance, histone acetylation reduces the positive charge of the histone proteins, thereby reducing their affinity for DNA and causing the chromatin to open (Figure 2).
How does the rate of acetylation affect drug levels? ›Slow acetylation may lead to higher blood levels of the drug and thus, to an increase in toxic reactions.
Where does N acetylation occur? ›N-acetylation, or the transfer of an acetyl group to nitrogen, occurs in almost all eukaryotic proteins through both irreversible and reversible mechanisms.
What does acetylation do in N regulation of gene expression? ›Histone acetylation is a critical epigenetic modification that changes chromatin architecture and regulates gene expression by opening or closing the chromatin structure. It plays an essential role in cell cycle progression and differentiation.
How does acetylation affect the rate of protein synthesis? ›Ribosome proteins play an important role in the protein synthesis, which could also be N-terminal acetylated. The N-terminal acetylation of the ribosome proteins may have an effect on protein synthesis. A decrease of 27% and 23% in the protein synthesis rate was observed with NatA and NatB deletion strains.
What is the opposite of acetylation? ›Acetylation is the process where an acetyl functional group is transferred from one molecule (in this case, acetyl coenzyme A) to another. Deacetylation is simply the reverse reaction where an acetyl group is removed from a molecule.
Does acetylation cause gene silencing? ›Histone acetylation was one of the earliest studied epigenetic mechanisms of transcriptional regulation, and it is known to be involved in numerous and diverse cellular processes, including cell-cycle progression, DNA repair, and gene silencing.
Is methylation the opposite of acetylation? ›What is the difference between acetylation and methylation? Acetylation is the process of the addition of acetyl molecules, whereas methylation is the process of the addition of methyl groups to the DNA molecule.
What happens in an acetylation reaction? ›
The Friedel–Crafts Acylation reaction involves formation of a complex between the Lewis acid and the chlorine atom of the acid chloride. An acylium ion is formed by the cleavage of C-Cl bond of the complex. The acylium ion has a positive charge on the carbon and is resonance stabilized.
What does the acetylation reaction do? ›What is the purpose of acetylation? Acetylation is needed for many industrial and pharmaceutical chemical reactions. It is also essential for chemical reactions in the body for forming proteins, processing drugs, and regulating and transcribing DNA.
What is the reaction of acetylation? ›Acetylation is a reaction that introduces an acetyl functional group (acetoxy group, CH3CO) into an organic chemical compound—namely the substitution of the acetyl group for a hydrogen atom—while deacetylation is the removal of an acetyl group from an organic chemical compound.
What is the acetylation of amines replacement? ›The acetylation / acylation of amines takes place when the acetyl group substitutes the active hydrogen atom(s) attached to the nitrogen atom of the amine.
How does acetylation cause an increase in expression of a gene? ›Acetylation usually occurs on lysine residues, neutralizing their positive charge and thereby causing histones to drift away from DNA, which has a negative charge. The released structure facilitates access to transcriptional machinery such as transcription factors and RNA polymerase II.
How does acetylation alter the activity of an enzyme? ›Acetylation neutralizes the lysine residue in the active site. Lysine has a positively charged ε-amino group due to protonation at physiological pH. Acetylation of the ε-amino group prevents protonation and thus abolishes the positive charge on the lysine side chain.
What are the different types of acetylation? ›There are currently three well-known forms of acetylation: Nα-acetylation, Nε-acetylation and O-acetylation (8).
What is acetylation in simple terms? ›(a-SEH-tih-LAY-shun) A chemical reaction in which a small molecule called an acetyl group is added to other molecules. Acetylation of proteins may affect how they act in the body.
What is acetylation also known as? ›Acetylation is a chemical reaction that is called ethanoylation in the IUPAC nomenclature. It describes a reaction that introduces an acetyl functional group into a chemical compound.
Which catalyst is used in acetylation? ›Typically acetylation of alcohols and phenols is performed under catalysis with acetic acid, acetyl chloride or acetic anhydride in the presence of a suitable basic [3] or acidic [4] catalyst. A variety of Lewis acids catalyzed acetylation of alcohols with acetic anhydride in solvent has been reported.