- Palladium-catalyzed cross-coupling reaction of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide
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A Suzuki-type cross-coupling of aryldioxaborolane with 2-bromo-N,N-dimethylacetamide in the presence of a catalytic amount of tricyclohexylphosphine as the ligand and hydroquinone as the free-radical scavenger has been demonstrated as a convenient and simple way for the synthesis of α-arylacetamide.
- Lu, Ting-Yi,Xue, Cuihua,Luo, Fen-Tair
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- Continuous Flow Acylation of (Hetero)aryllithiums with Polyfunctional N,N-Dimethylamides and Tetramethylurea in Toluene
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The continuous flow reaction of various aryl or heteroaryl bromides in toluene in the presence of THF (1.0 equiv) with sec-BuLi (1.1 equiv) provided at 25 °C within 40 sec the corresponding aryllithiums which were acylated with various functionalized N,N-
- Djukanovic, Dimitrije,Filipponi, Paolo,Heinz, Benjamin,Knochel, Paul,Mandrelli, Francesca,Martin, Benjamin,Mostarda, Serena
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supporting information
p. 13977 - 13981
(2021/09/13)
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- Direct defluorinative amidation-hydrolysis reaction of gem-difluoroalkenes with N,N-dimethylformamide, and primary and secondary amines
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A novel and efficient method for the synthesis of arylacetamides by the reactions of gem-difluoroalkenes with N,N-dialkylformamides, and primary and secondary amines with the assistance of KOtBu and water was developed.
- Wang, Biyun,Zhao, Xianghu,Liu, Qingyun,Cao, Song
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p. 8546 - 8552
(2018/12/01)
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- Amidation reaction of carboxylic acid with formamide derivative using SO3?pyridine
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The amidation reaction of carboxylic acid derivatives was developed using sulfur trioxide pyridine complex (SO3?py) as a commercially available and easily handled oxidant. This method could be applied to the reaction of various aromatic and aliphatic carboxylic acids, including optically active ones, with formamide derivatives to afford the corresponding amides in good to high yields.
- Kawano, Shota,Saito, Kodai,Yamada, Tohru
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supporting information
p. 584 - 586
(2018/04/12)
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- Facile Access to Amides from Oxygenated or Unsaturated Organic Compounds by Metal Oxide Nanocatalysts Derived from Single-Source Molecular Precursors
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Oxidative amidation is a valuable process for the transformation of oxygenated organic compounds to valuable amides. However, the reaction is severely limited by the use of an expensive catalyst and limited substrate scope. To circumvent these limitations, designing a transition-metal-based nanocatalyst via more straightforward and economical methodology with superior catalytic performances with broad substrate scope is desirable. To resolve the aforementioned issues, we report a facile method for the synthesis of nanocatalysts NiO and CuO by the sol-gel-assisted thermal decomposition of complexes [Ni(hep-H)(H2O)4]SO4 (SSMP-1) and [Cu(μ-hep)(BA)]2 (SSMP-2) [hep-H = 2-(2-hydroxylethyl)pyridine; BA = benzoic acid] as single-source molecular precursors (SSMPs) for the oxidative amidation of benzyl alcohol, benzaldehyde, and BA by using N,N-dimethylformamide (DMF) as the solvent and as an amine source, in the presence of tert-butylhydroperoxide (TBHP) as the oxidant, at T = 80 °C. In addition to nanocatalysts NiO and CuO, our previously reported Co/CoO nanocatalyst (CoNC), derived from the complex [CoII(hep-H)(H2O)4]SO4 (A) as an SSMP, was also explored for the aforementioned reaction. Also, we have carefully investigated the difference in the catalytic performance of Co-, Ni-, and Cu-based nanoparticles synthesized from the SSMP for the conversion of various oxygenated and unsaturated organic compounds to their respective amides. Among all, CuO showed an optimum catalytic performance for the oxidative amidation of various oxygenated and unsaturated organic compounds with a broad reaction scope. Finally, CuO can be recovered unaltered and reused for several (six times) recycles without any loss in catalytic activity.
- Mohammad, Akbar,Chandra, Prakash,Ghosh, Topi,Carraro, Mauro,Mobin, Shaikh M.
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p. 10596 - 10608
(2017/09/12)
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- Catalytic Enantioselective α-Fluorination of 2-Acyl Imidazoles via Iridium Complexes
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The first highly enantioselective α-fluorination of 2-acyl imidazoles utilizing iridium catalysis has been accomplished. This transformation features mild conditions and a remarkably broad substrate scope, providing an efficient and highly enantioselective approach to obtain a wide range of fluorine-containing 2-acyl imidazoles which are found in a variety of bioactive compounds and prodrugs. A large scale synthesis has also been tested to demonstrate the potential utility of this fluorination method.
- Xu, Guo-Qiang,Liang, Hui,Fang, Jie,Jia, Zhi-Long,Chen, Jian-Qiang,Xu, Peng-Fei
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supporting information
p. 3355 - 3358
(2016/12/09)
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- A novel method for the conversion of carboxylic acids to N,N-dimethylamides using N,N-dimethylacetamide as a dimethylamine source
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A simple, cost effective and environmentally benign method is reported for the preparation of N,N-dimethylamides from carboxylic acids. The versatility of the method is determined by synthesising a large number of N,N-dimethylamide derivatives. Carboxylic acids are heated at 160-165°C in N,N-dimethylacetamide solvent in the presence of1,1'-carbonyldiimidazole to afford the corresponding N,N-dimethylamides in good to excellent yields.
- Aavula, Sanjeev Kumar,Chikkulapally, Anil,Hanumanthappa,Jyothi, Indira,Vinod,Sulur, Kumar,Manjunatha,Sythana, Suresh Kumar
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p. 155 - 159
(2013/07/11)
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- Copper-catalyzed oxidative coupling of carboxylic acids with N,N-dialkylformamides: An approach to the synthesis of amides
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A new synthetic approach for amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. A new synthetic approach to amide bond formation through the oxidative coupling of N,N-dialkylformamides with carboxylic acids was achieved by using a copper catalyst and aqueous tert-butyl hydroperoxide (TBHP) as a sacrificial oxidant. Furthermore, this method was applied in the coupling of chiral amino acids in which the stereochemistry was retained in the resulting amide products. Copyright
- Kumar, P. Santhosh,Kumar, G. Sathish,Kumar, R. Arun,Reddy, N. Veera,Rajender Reddy
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supporting information
p. 1218 - 1222
(2013/04/10)
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- Continuous Method For Producing Amides Of Low Aliphatic Carboxylic Acids
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The invention relates to a continuous method for producing amides, according to which at least one carboxylic acid of formula (I) R3—COON ??(I) wherein R3 is hydrogen or an optionally substituted alkyl group comprising between 1 and 4 carbon atoms, is reacted with at least one amine of formula (II) HNR1R2 ??(II) wherein R1 and R2 are independently hydrogen or a hydrocarbon group comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is then reacted to form a carboxylic acid amide, under microwave irradiation in a reaction pipe, the longitudinal axis of the pipe being oriented in the direction of propagation of the microwaves of a monomode microwave applicator.
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Page/Page column 8
(2011/06/24)
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- Method For Producing Amides In The Presence Of Superheated Water
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The invention relates to a method for producing carboxylic acid amides, according to which at least one carboxylic acid of formula (I) [in-line-formulae]R3—COON ??(I)[/in-line-formulae] wherein R3 is hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 50 carbon atoms, is reacted with at least one amine of formula (II) [in-line-formulae]HNR1R2 ??(II)[/in-line-formulae] wherein R1 and R2 are independently hydrogen or an optionally substituted hydrocarbon radical comprising between 1 and 100 C atoms, to form an ammonium salt, and said ammonium salt is reacted in the presence of superheated water, under microwave irradiation, to form a carboxylic acid amide.
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Page/Page column 9
(2011/05/03)
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- PROCESS FOR THE PREPARATION OF ANTI-DEPRESSANT COMPOUND
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A process for the preparation of anti-depressant, compound of formula (I) or its pharmaceutically acceptable salts said process comprising reducing compound of formula (IIa) (wherein R is CONMe2) with sodium bis(2-methoxyethoxy) aluminium hydride followed by optional salt formation.
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Page/Page column 8
(2010/02/12)
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- Palladium-catalyzed conversion of benzylic and allylic halides into α-aryl and β,γ-unsaturated tertiary amides by the use of a carbamoylsilane
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Treatment of allylic and benzylic halides with N,N- dimethylcarbamoyl(trimethyl)silane in the presence of tetrakis- (triphenylphosphine)palladium(0) affords tertiary amides, which arise from the replacement of the halogen by the N,N-dimethylcarbamoyl group.
- Cunico, Robert F.,Pandey, Rajesh K.
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p. 9048 - 9050
(2007/10/03)
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- Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles
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2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48-75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.
- Shaughnessy, Kevin H.,Hamann, Blake C.,Hartwig, John F.
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p. 6546 - 6553
(2007/10/03)
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- Synthesis of N,N-dimethyl α-aryl and α,α-diarylacetamides by radical nucleophilic substitution reactions
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A family of N,N-dimethyl, α-aryl and α,α-diaryl acetamides was synthesized by reaction of aryl halides with N,N-dimethyl acetamide enolate ions in liquid ammonia.The reactions followed the SRN1 mechanism for nucleophilic substitution.They were initiated by light (350 nm), when the aryl halides or aryl halides bearing electron-donating groups were the substrate, and by potassium metal dissolved in liquid ammonia when the substituents on the aryl halides were electron-withdrawing groups. Key Words: SRN1 / nucleophilic substitution / synthesis / acetamide compounds / herbicides
- Palacios, S. M.,Asis, S. E.,Rossi, R. A.
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p. 111 - 116
(2007/10/02)
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- 2-Phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives: Synthesis and antidepressant activity
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A series of 2-phenyl-2-(1-hydroxycycloalkyl)ethylamine derivatives was examined for the ability to inhibit both rat brain imipramine receptor binding and the synaptosomal uptake of norepinephrine (NE) and serotonin (5-HT). Neurotransmitter uptake inhibition was highest for a subset of 2-phenyl-2-(1-hydroxycyclohexyl)dimethylethylamines in which the aryl ring has a halogen or methoxy substituent at the 3- and/or 4-positions. Potential antidepressant activity in this subset was assayed in three rodent models - the antagonism of reserpine-induced hypothermia, the antagonism of histamine-induced ACTH release, and the ability to reduce noradrenergic responsiveness in the rat pineal gland. An acute effect seen in the rat pineal gland with several analogues, including 1-[1-(3,4-dichlorophenyl)-2-(dimethylamino)ethyl]cyclohexanol (23) and 1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol (4), was taken as a possible correlate of a rapid onset of antidepressant activity. Compound 4 (venlafaxine) is presently undergoing clinical evaluation.
- Yardley,Morris Husbands,Stack,Butch,Bicksler,Moyer,Muth,Andree,Fletcher III,James,Sielecki
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p. 2899 - 2905
(2007/10/02)
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