- A simple and convenient synthesis of N-formyl amino acid esters under mild conditions
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A variety of amino acid ester hydrochlorides react with cyanomethyl formate at room temperature to give the N-formyl amino acid esters in good yields and without racemization.
- Duczek,Deutsch,Vieth,Niclas
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Read Online
- Capsicum annuum fruit extract: A novel reducing agent for the green synthesis of zno nanoparticles and their multifunctional applications
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A simple, efficient and convenient method for the preparation of zinc oxide (ZnO) nanoparticle was described. Several parameters like size and morphology of the prepared nanoparticles were characterized thorough a variety of analytical techniques such as
- Lalithamba, Haraluru Shankraiah,Raghavendra, Mahadevaiah,Uma, Kogali,Yatish, Kalanakoppal Venkatesh,Mousumi, Das,Nagendra, Govindappa
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p. 354 - 364
(2018/07/05)
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- Elucidating the Reaction Pathway of Decarboxylation-Assisted Olefination Catalyzed by a Mononuclear Non-Heme Iron Enzyme
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Installation of olefins into molecules is a key transformation in organic synthesis. The recently discovered decarboxylation-assisted olefination in the biosynthesis of rhabduscin by a mononuclear non-heme iron enzyme (P.IsnB) represents a novel approach in olefin construction. This method is commonly employed in natural product biosynthesis. Herein, we demonstrate that a ferryl intermediate is used for C-H activation at the benzylic position of the substrate. We further establish that P.IsnB reactivity can be switched from olefination to hydroxylation using electron-withdrawing groups appended on the phenyl moiety of the analogues. These experimental observations imply that a pathway involving an initial C-H activation followed by a benzylic carbocation species or by electron transfer coupled β-scission is likely utilized to complete C=C bond formation.
- Yu, Cheng-Ping,Tang, Yijie,Cha, Lide,Milikisiyants, Sergey,Smirnova, Tatyana I.,Smirnov, Alex I.,Guo, Yisong,Chang, Wei-Chen
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supporting information
p. 15190 - 15193
(2018/11/23)
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- Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions
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A highly efficient and mild transamidation of amides with amines co-catalysed by borinic acid and acetic acid has been reported. A wide range of functionalised formamides was synthesized in excellent yields, including important chiral α-amino acid derivatives, with minor racemisation being observed. Experiments suggested that the reaction rely on a cooperative catalysis involving an enhanced boron-derived Lewis acidity rather than an improved Br?nsted acidity of acetic acid. Amide bonds are reputedly difficult to activate due to their high resonance stabilization. An unusual mild activation of dimethylformamide and formamide by borinic acid 1 (see scheme), illustrated by a general formylation of a wide range of amines, including chiral α-amino esters, has been reported.
- Mohy El Dine, Tharwat,Evans, David,Rouden, Jacques,Blanchet, Jér?me
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supporting information
p. 5894 - 5898
(2016/04/26)
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- A metal-free approach for transamidation of amides with amines in aqueous media
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An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).
- Srinivas, Mahesuni,Hudwekar, Abhinandan D.,Venkateswarlu, Vunnam,Reddy, G. Lakshma,Kumar, K. A. Aravinda,Vishwakarma, Ram A.,Sawant, Sanghapal D.
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supporting information
p. 4775 - 4779
(2015/07/20)
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- Transamidation of carboxamides catalyzed by Fe(III) and water
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The highly efficient transamidation of several primary, secondary, and tertiary amides with aliphatic and aromatic amines (primary and secondary) is described. The reaction is performed in the presence of a 5 mol % concentration of different hydrated salts of Fe(III), and the results show that the presence of water is crucial. The methodology was also applied to urea and phthalimide to demonstrate its versatility and wide substrate scope. An example of its use is an intramolecular application in the synthesis of 2,3-dihydro-5H-benzo[b]-1,4- thiazepin-4-one, which is the bicyclic core of diltiazem and structurally related drugs (Budriesi, R.; Cosimelli, B.; Ioan, P.; Carosati, E.; Ugenti, M. P.; Spisani, R. Curr. Med. Chem. 2007, 14, 279-287). A plausible mechanism that explains the role of water is proposed on the basis of experimental observations and previous mechanistic suggestions for transamidation reactions catalyzed by transition metals such as copper and aluminum. This methodology represents a significant improvement over other existing methods; it can be performed in air and with wet or technical grade solvents.
- Becerra-Figueroa, Liliana,Ojeda-Porras, Andrea,Gamba-Sánchez, Diego
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p. 4544 - 4552
(2014/06/09)
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- Synthesis of N-methyl L-phenylalanine for total synthesis of pepticinnamin e
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The target compounds 3, 10 and 11 were synthesized through different N-methylation strategies. The concise and efficient preparation of them in large scale was developed and 3, 10 and 11 were obtained in suitable form used for both nitrogen-end and oxygen-end extension in next coupling reaction in peptides synthesis, specifically in total synthesis of natural pepticinnamin E.
- Sun, Dequn,Zhang, Lingzi,Wang, Jin
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scheme or table
p. 319 - 322
(2012/09/07)
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- Sulfated tungstate catalyzed highly accelerated N-formylation
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Sulfated tungstate catalyzed, green, rapid, and practical method for N-formylation of amines using formic acid under solvent-free conditions is described. This method showed improvements over the reported in terms of yield, reaction time, and chemoselectivity.
- Pathare, Sagar P.,Sawant, Ravindra V.,Akamanchi, Krishnacharya G.
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experimental part
p. 3259 - 3263
(2012/07/30)
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- Investigation of the configurational stabilities of chiral isocyanoacetates in multicomponent reactions
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Isocyanoacetates are uniquely reactive compounds characterized by an ambivalent isocyano functional group and an enolizable α-carbon. It is widely believed that chiral α-substituted isocyanoacetates are configurationally unstable in some synthetically use
- Carney, Daniel W.,Truong, Jonathan V.,Sello, Jason K.
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experimental part
p. 10279 - 10285
(2012/02/14)
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- Isoselenocyanates derived from amino acid esters: An expedient synthesis and application to the assembly of selenoureidopeptidomimetics, unsymmetrical Selenoureas and selenohydantoins
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An important class of organoselenium compounds-α-isoselenocyanato esters 4 hasbeen prepared by a reaction of α-isocyano esters with elemental selenium powder. The reaction issimple, rapid and all the isoselenocyanates havebeen isolated as stable ones after chromatographic purification. These hitherto unreported classes of molecules would be useful building blocks for the preparation of variety of selenium containing peptidomimetics. In this study, the utility of the title molecules in the preparation of selenoureidopeptidomimetics 6, unsymmetrical selenoureas 8 and selenohydantoins 10 isdemonstrated.
- Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
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scheme or table
p. 644 - 651
(2011/09/14)
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- Sulfonic acid supported on hydroxyapatite-encapsulated-γ-Fe2O3 nanocrystallites as a magnetically Br?nsted acid for N-formylation of amines
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Treatment of aqueous formic acid (85%) with structurally diverse amines in the presence of a catalytic amount of sulfonic acid supported on hydroxyapatite-encapsulated-γ-Fe2O3 [HAp@-γ-Fe2O3] (0.9 mol.%) as a heterogeneous, reusable and highly efficient catalyst gave the corresponding formamides in good to excellent yields at room temperature. The magnetically catalytic system was recovered by-passing time consuming filtration operation by using an external magnet device. In addition to facility, this methodology, it also enhances product purity and promises economic as well as environmental benefits.
- Ma'mani, Leila,Sheykhan, Mehdi,Heydari, Akbar,Faraji, Mohammad,Yamini, Yadollah
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experimental part
p. 64 - 69
(2010/07/05)
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- A convenient one-pot synthesis of formamide derivatives using thiamine hydrochloride as a novel catalyst
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Formamide derivatives have been synthesized in excellent yields from amine and formic acid in the presence of a catalytic amount of thiamine hydrochloride (VB1) at 80 °C. The advantages of this method are the use of a cheap, stable, non-toxic, and readily available catalyst, easy work-up, improved yields, and solvent-free conditions.
- Lei, Min,Ma, Lei,Hu, Lihong
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experimental part
p. 4186 - 4188
(2010/09/12)
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- Indium-catalyzed N -formylation of amines under solvent-free conditions
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We have developed a simple, mild method for N-formylation of a wide variety of amines in the presence of indium metal as a catalyst under solvent-free conditions. This reaction is applicable to the chemoselective N-formylation of amino groups and -amino acid esters without epimerization. Georg Thieme Verlag Stuttgart.
- Kim, Joong-Gon,Jang, Doo Ok
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experimental part
p. 1231 - 1234
(2010/07/08)
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- Facile and highly efficient N-formylation of amines using a catalytic amount of iodine under solvent-free conditions
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We developed a simple, practical, and catalytic method for the N-formylation of a wide variety of amines in the presence of molecular iodine as a catalyst under solvent-free conditions. This reaction is applicable to the chemoselective N-formylation of amino groups and -amino acid esters without epimerization.
- Kim, Joong-Gon,Jang, Doo Ok
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experimental part
p. 2093 - 2096
(2010/10/03)
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- Process for preparing nitriles and isonitriles by dehydration reactions with propanephosphonic anhydrides
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The invention concerns a method for producing: a) nitriles of formula (II) and b) isonitriles of formula (III) by reacting: a) carboxylic acid amides (RCO—NH2), ammonium salts of carboxylic acids (RCOO—NH4+) or carboxylic acids in the presence of ammonia or ammonium salts (RCOOH+NH3, RCOOH+NH4+) or b) formamides (H—CO—NHR) or mixtures of amines with formic acid, with cyclic phosphonic acid anhydrides while eliminating water at a temperature ranging from ?30 to +120° C., in which R represents an arbitrarily substituted linear or branched C1-C8 alkyl radical, a C3-C10 cycloalkyl radical, alkenyl radical, alkynyl radical or an aryl radical or heteroaryl radical. As a cyclic phosphonic acid anhydride, a 2,4,6,-substituted 1,3,5,2,4,6 -trioxatriphosphinane-2,4,6-trioxide of formula (I) is advantageously used, in which: x=3, 4 or 5; R′, independent of one another, represents open-chain or branched, saturated or unsaturated, straight-chain C1to C16 alkyl radicals or cyclic C3 to C16 alkyl radicals or aryl or heteroaryl.
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- AMINE-BASED AND AMIDE-BASED INHIBITORS OF SEMICARBAZIDE-SENSITIVE AMINE OXIDASE (SSAO) ENZYME ACTIVITY AND VAP-1 MEDIATED ADHESION USEFUL FOR TREATMENT OF DISEASES
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Compositions and methods are disclosed for inhibiting semicarbazide-sensitive amine oxidase (SSAO), also known as vascular adhesion protein-1 (VAP-1). The compounds disclosed are amine-containing and amide-containing compounds. The compounds and compositions are useful for treatment of diseases, including inflammation, inflammatory diseases and autoimmune disorders.
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Page/Page column 96
(2010/02/13)
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- A new, simple procedure for the synthesis of formyl amides
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A simple and mild method for the N-formylation of amines and α-amino esters is described via reaction with 2-chloro-4,6-dimethoxy[1,3,5]triazine and formic acid. The reaction can be accelerated under microwave irradiation and yields the N-formyl species in high yields and without racemization in the case of optically active α-amino esters.
- De Luca, Lidia,Giacomelli, Giampaolo,Porcheddu, Andrea,Salaris, Margherita
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p. 2570 - 2572
(2007/10/03)
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- A mild method for formylating amino esters without using any formulating agent
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A simple and mild method for the N-formylation of α-amino esters is described via an intermediate oxaziridine. This procedure avoids the necessity of specific formylating agents and yields the N-formyl species in high yield and without racemization.
- Giard, Thierry,Bénard, Didier,Plaquevent, Jean-Christophe
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p. 297 - 300
(2007/10/03)
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- THE TRANSFORMYLATION REACTION - TRANSFER OF AN N-FORMYL RESIDUE IN AMINO ACID AND PEPTIDE DERIVATIVES TO NUCLEOPHILIC GROUPS - AS A SIDE REACTION OF PEPTIDE SYNTHESIS
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In the course of a study of the enzymatic synthesis of peptides from N-formylamino acids, the transfer of a formyl group to nucleophilic acceptors present in the aqueous-organic reaction medium - amino acid esters, peptides, and aromatic amines - has been detected, and this to the greater degree the higher the nucleophilicity of the acceptor.The transfer of a formyl group from a number of formylamino acids and formylpeptides to phenylalanine methyl ester has been studied.A fall in the yield of the transformylation reaction on passing from formyl derivatives with a free carboxy group to formyl peptides or esterified formylamino acids has been found.No transfer of an acetyl group was observed under these conditions.On the use of formyl derivatives in peptide synthesis the possibility of the occurrence of the transformylation reaction and the resulting appearance of by-products must be taken into account.Key words: peptide; enzymatic synthesis; transformylation.
- Kotlova, E. K.,Levin, E. D.,Yusupova, M. P.,Rozynov, B. V.,Stepanov, V. M.
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p. 678 - 686
(2007/10/02)
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- The Application of Nα-Formyl Amino Acid Esters in the Enzyme-Catalyzed Peptide Synthesis
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The synthesis of Nα-formyl protected amino acid esters and their use in kinetically controlled α-chymotrypsin-, trypsin- and carboxypeptidase Y-catalyzed peptide synthesis is described.Using the synthesis of H-Tyr-Ala-OH as example it is demons
- Floersheimer, Andreas,Kula, Maria-Regina
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p. 1323 - 1331
(2007/10/02)
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- SYNTHESE D'AMINOPHOSPHINEPHOSPHINITES CHIRAUX. UTILISATION EN REDUCTION ASYMETRIQUE CATALYTIQUE
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The chiral aminophosphinephosphinites ligands (AMPP) are directly synthesized from natural amino alcohols or by reduction of formyl esters of α-amino acids and PPh2Cl. Their cationic rhodium complexes have been found to be excellent catalysts for enantioselective hydrogenation of dehydroamino acids (ee ca. 86percent, yield ca. 100percent) for example.Asymmetric reduction of ketones can also be performed with the new alkyl AMPP* modified rhodium catalyst (ee 50percent).
- Karim, A.,Mortreux, A.,Petit, F.,Buono, G.,Pfeiffer, G.,Siv, C.
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