10264-09-2Relevant articles and documents
Efficient procedure for the preparation of amides using polymer-bound reagents
Buchstaller,Ebert,Anlauf
, p. 1001 - 1005 (2001)
An effective method for the conversion of acids into amides is presented. The two-step procedure includes the preparation of acid chloride intermediates using Pol-Ph3P and subsequent treatment of these intermediates with amines and polymer-bound base. The amides were accessible in high yields and purities without further purification.
Synthesis of amides from esters and amines under microwave irradiation
Zradni, Fatima-Zohra,Hamelin, Jack,Derdour, Aicha
, p. 3525 - 3531 (2002)
Formamide, primary and secondary amines react with esters in the presence of potassium tert-butoxide under microwave irradiation. Substituted amides are formed in yields (generally more than 70%) much higher than under conventional heating.
MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines
Gu, Liuqun,Lim, Jaehong,Cheong, Jian Liang,Lee, Su Seong
, p. 7017 - 7019 (2014)
For efficient direct amide condensations, a new class of catalysts are developed by immobilizing boronic acids on mesocellular siliceous foam. Associated with their large pores, the microenvironments surrounding the immobilized active species greatly influence the catalytic activity. The fluoroalkyl moieties on the silica surface significantly enhance the catalytic performance along with easy recovery and reuse. This approach proposes a potential way to optimize various types of silica-supported catalysts. the Partner Organisations 2014.
The Selective N-Monoalkylation of Amides with Alkyl Halides in the Presence of Alumina and KOH
Sukata, Kazuaki
, p. 838 - 843 (1985)
The effects of alumina impregnated with KOH (KOH/Al2O3) and a mixture of alumina and powdered KOH (KOH+Al2O3) have been examined using the alkylation of benzamide under various conditions.In each case, alkylation occurs exclusively in the pores of the alumina, the extent depending upon the alumina-pore size.For both yield and selectivity for N-monoalkylation, KOH+Al2O3 is superior to KOH/Al2O3.Dioxane is the best of the solvents employed.It is proposed that, in dioxane, an enolate-like species, PhC(O-K+)=NR', exists as stable ion pair aggregates, which are true reactants in the pore.This method, using KOH/Al2O3 or KOH+Al2O3, has been applied to N-alkylation of the other amides, giving the N-monoalkylated products in substantial yields with extremely high selectivities. 2-Phenylacetamide is regioselectively N-monoalkylated in high yields.This regioselectivity is explained in terms of steric hindrance.
Direct Regioselective Synthesis of Tetrazolium Salts by Activation of Secondary Amides under Mild Conditions
Tona, Veronica,Maryasin, Boris,De La Torre, Aurélien,Sprachmann, Josefine,González, Leticia,Maulide, Nuno
, p. 2662 - 2665 (2017)
Tetrazolium salts are biologically active molecules that have found broad applications in biochemical assays. A regioselective synthesis of tetrazolium salts is described through a formal (3 + 2) cycloaddition. The possibility of employing simple amides and azides as starting material and the mild conditions allow a broad functional group tolerance.
Amination of pyridylketenes: Experimental and computational studies of strong amide enol stabilization by the 2-pyridyl group
Acton, Austin W.,Allen, Annette D.,Antunes, Luis M.,Fedorov, Andrei V.,Najafian, Katayoun,Tidwell, Thomas T.,Wagner, Brian D.
, p. 13790 - 13794 (2002)
Laser flash photolyses of 2-, 3-, and 4-diazoacetylpyridines 8 give the corresponding pyridylketenes 7 formed by Wolff rearrangements, as observed by time-resolved infrared spectroscopy, with ketenyl absorptions at 2127, 2125, and 2128 cm-1, re
[Co(MeTAA)] Metalloradical Catalytic Route to Ketenes via Carbonylation of Carbene Radicals
Chirila, Andrei,van Vliet, Kaj M.,Paul, Nanda D.,de Bruin, Bas
, p. 2251 - 2258 (2018)
An efficient synthetic strategy towards beta-lactams, amides, and esters involving “in situ” generation of ketenes and subsequent trapping with nucleophiles is presented. Carbonylation of carbene radical intermediates using the cheap and highly active cobalt(II) tetramethyltetraaza[14]annulene catalyst [Co(MeTAA)] provides a convenient one-pot synthetic protocol towards substituted ketenes. N-tosylhydrazones are used as carbene precursors, thereby bridging the gap between aldehydes and ketenes. Activation of these carbene precursors by the metalloradical cobalt(II) catalyst affords CoIII-carbene radicals, which subsequently react with carbon monoxide to form ketenes. In the presence of a nucleophile (imine, alcohol, or amine) in the reaction medium the ketene is immediately trapped, resulting in the desired products in a one-pot synthetic protocol. The β-lactams formed upon reaction with imines are produced in a highly trans-selective manner.
Thoination of N-alkyl-O-acyl hydroxamic acid derivatives via Lawesson's reagent
Al-Faiyz, Yasair S.S.
, (2021/10/02)
N-alkyl-O-acyl thiohydroxamic acid derivatives were prepared in good yields by the treatment of their parent hydroxamic acids with Lawesson's reagent. Some of these thiohydroxamic acid derivatives exhibit the ability to undergo rearrangement under basic c
Carboxyesterase polypeptides for amide coupling
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Page/Page column 59-60; 65-66; 79-81, (2021/05/28)
The present invention provides engineered carboxyesterase enzymes having improved properties as compared to a naturally occurring wild-type carboxyesterase enzymes, as well as polynucleotides encoding the engineered carboxyesterase enzymes, host cells capable of expressing the engineered carboxyesterase enzymes, and methods of using the engineered carboxyesterase enzymes in amidation reactions.
An Efficient Palladium-Catalysed Aminocarbonylation of Benzyl Chlorides
Oram, Niall,Richardson, Jeffery,Rilvin-Derrick, Eloise
, p. 369 - 372 (2020/02/27)
An improved procedure for the aminocarbonylation of benzyl chloride derivatives using carbon monoxide and either primary or secondary amines has been developed. Studying the competing background alkylation reaction allowed the solvent and base to be selected for a simple catalyst screen, which, in turn, enabled the discovery of a method for the preparation of 2-arylacetamides under mild conditions, with minimal side-products using an inexpensive phosphine ligand. This non-traditional optimisation strategy allowed us to overcome the background alkylation, which has been cited as justification for the development of more complex and less atom-economical approaches.