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Towards environmentally benign capture and conversion: Heterogeneous metal catalyzed CO2 hydrogenation in CO2 capture solvents
The transformation of captured CO2 into value-added chemicals to mitigate increasing CO2 concentration in the atmosphere has gained significant attention recently. Though carbon capture and storage (CCS) is already being practiced in a few places, it suffers from energy-intensive CO2 desorption and compression steps involved, which can be avoided in the carbon capture and utilization (CCU) approach. Herein, a selection of carbon capture solvents were screened to assess the reactivity of condensed-phase heterogeneous metal catalyzed hydrogenation of CO2. Among the catalysts screened, the Cu/ZnO/Al2O3 catalyst was active for the one-pot CO2 capture and conversion process to methanol using post and pre-combustion carbon capture solvents comprised of various amines and alcohols. Our findings indicate that formamides are less-reactive under our conditions in comparison with formate ester intermediates and a combination of 1° alcohols and amines gives the highest methanol yield. Screening volatile organic compound (VOC)-free alcohols and amines led us to an environmentally benign system of bio-derived and biodegradable chitosan and polyethylene glycol (PEG200), which provide a moderate concentration of methanol (139.5 mmol L-1) with the facile separation of volatile products (water and methanol). The chitosan/PEG200 system was recycled three times, ultimately providing a promising VOC-free, biodegradable, bio-derived and recyclable CO2 capture and conversion pathway.
Kothandaraman, Jotheeswari,Heldebrant, David J.
p. 828 - 834
(2020)
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Catalytic N-diphosphonomethylation of amino alkanols and bisamino alkanes using tris(trimethylsilyl) phosphite as a convenient synthon
The new mono- and bis(aminomethylenediphosphonic) acids are synthesized for the first time via unique reaction of tris(trimethylsilyl) phosphite and various N-formyl amino alkanols or bis(N-formyl amino) alkanes at the presence of effective catalyst – trimethylsilyl triflate under mild conditions. The further treatment of initially formed trimethylsilyl intermediates with the methanol excess resulted in the crystalline mono- and bis(aminomethylenediphosphonic) acids in high yields. The catalytic scheme of target substances formation is proposed and discussed in detail. The structures of target acids were confirmed by the 1H, 13C, 31P NMR spectra and high resolution mass spectra (HRMS). The resulting compounds are of great interest as perspective bioactive substances with versatile properties and effective polydentate ligands.
Prishchenko, Andrey A.,Alekseyev, Roman S.,Novikova, Olga P.,Livantsov, Mikhail V.,Livantsova, Ludmila I.,Petrosyan, Valery S.
supporting information

(2021/11/09)

Highly Efficient and Selective N-Formylation of Amines with CO2 and H2 Catalyzed by Porous Organometallic Polymers
The valorization of carbon dioxide (CO2) to fine chemicals is one of the most promising approaches for CO2 capture and utilization. Herein we demonstrated a series of porous organometallic polymers could be employed as highly efficient and recyclable catalysts for this purpose. Synergetic effects of specific surface area, iridium content, and CO2 adsorption capability are crucial to achieve excellent selectivity and yields towards N-formylation of diverse amines with CO2 and H2 under mild reaction conditions even at 20 ppm catalyst loading. Density functional theory calculations revealed not only a redox-neutral catalytic pathway but also a new plausible mechanism with the incorporation of the key intermediate formic acid via a proton-relay process. Remarkably, a record turnover number (TON=1.58×106) was achieved in the synthesis of N,N-dimethylformamide (DMF), and the solid catalysts can be reused up to 12 runs, highlighting their practical potential in industry.
Shen, Yajing,Zheng, Qingshu,Chen, Zhe-Ning,Wen, Daheng,Clark, James H.,Xu, Xin,Tu, Tao
supporting information
p. 4125 - 4132
(2021/01/12)

Preparation method of N-vinyl alkylamide
The invention relates to the technical field of vinyl compound production, in particular to a preparation method of Nvinyl alkyl amide. The preparation method comprises the following steps: A) under the action of a composite basic catalyst, reacting acetaldehyde with alkylamide to obtain Nhydroxyethyl alkylamide, and carrying out esterification reaction on the obtained Nhydroxyethyl alkylamide andacid anhydride to obtain an ester compound; wherein the composite basic catalyst comprises an inorganic base and an amine compound; and B) carrying out medium-temperature cracking on the ester compound, and carrying out vacuum distillation to obtain the Nvinyl alkylamide. Research finds that inorganic base and amine compounds are adopted as catalysts at the same time, so that the dosage of a basic catalyst required by reaction of Nhydroxyethyl alkylamide and anhydride can be remarkably reduced, the temperature required by subsequent cracking reaction is reduced, a reaction system tends to bemilder, and the reaction yield is improved. The yield and the purity of a reaction product can be remarkably improved while the energy consumption is reduced.
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Paragraph 0065-0066; 0071-0072

(2020/12/29)

Facile access to: N-formyl imide as an N-formylating agent for the direct synthesis of N-formamides, benzimidazoles and quinazolinones
N-Formamide synthesis using N-formyl imide with primary and secondary amines with catalytic amounts of p-toluenesulfonic acid monohydrate (TsOH·H2O) is described. This reaction is performed in water without the use of surfactants. Moreover, N-formyl imide is efficiently synthesized using acylamidines with TsOH·H2O in water. In addition, N-formyl imide was successfully used as a carbonyl source in the synthesis of benzimidazole and quinazolinone derivatives. Notable features of N-formylation of amines by using N-formyl imide include operational simplicity, oxidant- A nd metal-free conditions, structurally diverse products, and easy applicability to gram-scale operation.
Huang, Hsin-Yi,Liang, Chien-Fu,Lin, Xiu-Yi,Yen, Shih-Yao
supporting information
p. 5726 - 5733
(2020/08/21)

PHOTO-REDOX TITANIUM CONTAINING ORGANIC FRAMEWORKS AND METHODS OF MAKING AND USE THEREOF
Disclosed herein are metal-organic frameworks and methods of making and use thereof.
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Paragraph 0165; 0172-0173

(2020/07/07)

METHOD OF CARBON MONOXIDE FIXATION AND METHOD OF AMINE FORMYLATION
The present invention relates to a method for fixing carbon monoxide in a metal-free condition and a method for formating amine using the same.
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Paragraph 0078; 0081-0085; 0096-0098

(2021/02/19)

Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
p. 4297 - 4306
(2019/08/26)

Metal-free Carbon Monoxide (CO) Capture and Utilization: Formylation of Amines
The capture and utilization of CO by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) were performed in the absence of transition-metal complexes. The reaction of TBD with CO afforded TBD-CO adducts, which were converted to formylated TBD (TBD-CHO). TBD-CO adducts may include an interaction of CO with positively charged species based on NMR and IR analysis. In the presence of amines, CO was transferred from TBD-CO to amines, producing formylated amines with good yields. The reaction mechanism involving TBD-CO adducts is presented based on theoretical calculations. (Figure presented.).
Noh, Hyeong-Wan,An, Youngjoon,Lee, Seulchan,Jung, Jaehoon,Son, Seung Uk,Jang, Hye-Young
(2019/04/26)

Rapid synthesis method of biomass-based amide
The invention discloses a rapid synthesis method of biomass-based amide, which comprises the steps: formamide is used as an amine source, formic acid is used as a hydrogen source, biomass aldehyde andketone is used as a raw material, the direct addition of formamide and aldehyde and ketone components and the reduction of formic acid is promoted to prepare the corresponding formamide derivative byrapidly heating under microwave-assisted heating and in the absence of a solvent and a catalyst; the formamide derivative is selectively converted to the corresponding primary amide by alcoholysis under the action of a base. The microwave assisted heating reaction system of the invention has higher catalytic efficiency than the corresponding oil bath system, greatly shortens the reaction time, remarkably improves the selectivity. The conversion rate of the biomass aldehyde or ketone compound is at least 99%, and the yield of the formamide derivative can reach 85 to 99%; the formamide can be synthesized by alcoholysis to obtain a primary amide with a yield of 92 to 99%.
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Paragraph 0052-0054; 0057

(2019/01/15)

Selective Iron-Catalyzed N-Formylation of Amines using Dihydrogen and Carbon Dioxide
A family of iron(II) carbonyl hydride species supported by PNP pincer ligands was identified as highly productive catalysts for the N-formylation of amines via CO2 hydrogenation. Specifically, iron complexes supported by two different types of PNP ligands were examined for formamide production. Complexes containing a PNP ligand with a tertiary amine afforded superior turnover numbers in comparison to complexes containing a bifunctional PNP ligand with a secondary amine, indicating that bifunctional motifs are not required for catalysis. Systems incorporating a tertiary amine containing a PNP ligand were active for the N-formylation of a variety of amine substrates, achieving TONs up to 8900 and conversions as high as 92%. Mechanistic experiments suggest that N-formylation occurs via an initial, reversible reduction of CO2 to ammonium formate followed by dehydration to produce formamide. Several intermediates relevant to this reaction pathway, as well as iron-containing deactivation species, were isolated and characterized.
Jayarathne, Upul,Hazari, Nilay,Bernskoetter, Wesley H.
p. 1338 - 1345
(2018/02/14)

An Efficient Ruthenium Catalyst Bearing Tetradentate Ligand for Hydrogenations of Carbon Dioxide
A ruthenium complex with a tetradentate bipyridine ligand was proved to be a highly efficient catalyst for the conversions of CO2. Turnover numbers up to 300 000, 9800, and 2100 were achieved for the hydrogenations of CO2 to formamides, formamides to methanol and amines, and the direct hydrogenation of CO2 to methanol, respectively.
Zhang, Feng-Hua,Liu, Chong,Li, Wei,Tian, Gui-Long,Xie, Jian-Hua,Zhou, Qi-Lin
supporting information
p. 1000 - 1002
(2018/09/21)

N-formylation of amine using graphene oxide as a sole recyclable metal-free carbocatalyst
Abstract: Graphene oxide (GO), an inexpensive, environment-friendly, and metal-free carbocatalyst, used for the N-formylation of amines is developed. In this reaction, GO shows good activity, selectivity, and recyclability. This strategy has an array of advantages, such as being metal free, without additive, wide-scope protocol, scalable with a low catalyst loading of 3?wt%, use of readily available and recyclable carbocatalyst, and DMF as a readily available formyl source. Furthermore, this strategy provides an avenue for the convenient hydroformylation of various amines. Graphical abstract: [Figure not available: see fulltext.].
Ma, Juan,Zhang, Jingyu,Zhou, Xiao,Wang, Jiawei,Gong, Hang
p. 2851 - 2860
(2018/10/31)

METHOD FOR PREPARING FORMAMIDE COMPOUND
Disclosed is a method for preparing a formamide compound, the method uses carbon dioxide, hydrogen and an amine compound as raw materials and a transition metal complex as a catalyst, and the reaction is carried out in an organic solvent or in the absence of a solvent to form a formamide compound. The method of the present invention is an effective method of chemical utilization of carbon dioxide, which has the advantages of high reaction efficiency, a good selectivity, mild conditions, economic and environmental protection, being simple and convenient to operate and the like, and has a good popularization and application prospect.
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Paragraph 0219-0222

(2018/02/28)

Systematic variation of the optical bandgap in titanium based isoreticular metal-organic frameworks for photocatalytic reduction of CO2 under blue light
A series of metal-organic frameworks isoreticular to MIL-125-NH2 were prepared, where the 2-amino-terephthalate organic links feature N-alkyl groups of increasing chain length (from methyl to heptyl) and varying connectivity (primary and secondary). The prepared materials display reduced optical bandgaps correlated with the inductive donor ability of the alkyl substituent as well as high photocatalytic activity towards the reduction of carbon dioxide under blue illumination operating over 120 h. Secondary N-alkyl substitution (isopropyl, cyclopentyl and cyclohexyl) exhibits larger apparent quantum yields than the primary N-alkyl analogs directly related to their longer lived excited-state lifetime. In particular, MIL-125-NHCyp (Cyp = cyclopentyl) exhibits a small bandgap (Eg = 2.30 eV), a long-lived excited-state (τ = 68.8 ns) and a larger apparent quantum yield (Φapp = 1.80%) compared to the parent MIL-125-NH2 (Eg = 2.56 eV, Φapp = 0.31%, τ = 12.8 ns), making it a promising candidate for the next generation of photocatalysts for solar fuel production based on earth-abundant elements.
Logan, Matthew W.,Ayad, Suliman,Adamson, Jeremy D.,Dilbeck, Tristan,Hanson, Kenneth,Uribe-Romo, Fernando J.
supporting information
p. 11854 - 11863
(2017/07/10)

Preparation method of formamide compound
The invention provides a preparation method of a formamide compound. A preparation process of the preparation method comprises the following steps: uniformly mixing formic acid and an amine compound raw material selected from primary amine or secondary amine to prepare a homogeneous reaction system; raising the temperature of the homogeneous reaction system to 160 DEG C to 230 DEG C; decomposing the homogeneous reaction system to obtain carbon monoxide and enabling the carbon monoxide to participate in reaction; collecting a reaction product to obtain the formamide compound. The invention provides a novel technology for synthesizing the formamide compound through a heterogeneous method; a catalyst does not need to be used in a reaction process and an operation process is simple and controllable; the selectivity of the amine compound raw material is high.
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Paragraph 0110-0113

(2018/03/24)

Formamide Synthesis through Borinic Acid Catalysed Transamidation under Mild Conditions
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
supporting information
p. 5894 - 5898
(2016/04/26)

Highly efficient ruthenium-catalyzed N-formylation of amines with H2 and CO2
A highly efficient catalyst system based on ruthenium-pincer-type complexes has been discovered for N-formylation of various amines with CO2 and H2, thus affording the corresponding formamides with excellent productivity (turnover numbers of up to 1940000 in a single batch) and selectivity. Using a simple catalyst recycling protocol, the catalyst was reused for 12 runs in N,N-dimethylformamide production without significant loss of activity, thus demonstrating the potential for practical utilization of this cost-effective process.
Zhang, Lei,Han, Zhaobin,Zhao, Xiaoyu,Wang, Zheng,Ding, Kuiling
supporting information
p. 6186 - 6189
(2015/05/20)

Colloid and nano-sized catalysts in organic synthesis: X. Synthesis of carboxamides by direct amidation of carboxylic acids and transamidation catalyzed by colloid copper
Abstract It was found that in the presence of colloid copper the direct amidation of some carboxylic acids with primary and secondary amines in benzene with azeotropic distillation of water became possible. The catalyst was proven to be suitable also for transamidation reaction of a number of carboxylic acid amides under mild conditions in solvent-free conditions.
Mokhov,Popov, Yu. V.,Budko
p. 820 - 826
(2015/06/08)

TETRAHYDRO-TETRAZOLO[1,5-A]PYRAZINES AS ROR-GAMMA INHIBITORS
The present invention relates to tetrahydro-tetrazolo[l,5-a]pyrazine compounds of formula (I), wherein R1 denotes -R3, -CH2-R3 or -CO-R3; R2 denotes Ar2, Hetar2 or C3-7-cycloalkyl; and R3 denotes Ar3, Hetar3 or C3-7-cycloalkyl. These compounds are useful for inhibiting the retinoid-related orphan receptor γ (ROR γ, ROR-gamma) and for the prevention and/or treatment of medical conditions affected by ROR γ activity such as rheumatoid arthritis, multiple sclerosis, psoriasis, ulcerative colitis, asthma, autoimmune hepatitis or type 1 and type 2 diabetes.
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Page/Page column 50

(2015/07/07)

New heterometallic Ir(iii)2-Eu(iii) complexes: White light emission from a single molecule
The design of a relatively simple bifunctional ligand led to the obtainment of three new Ir(iii)2-Eu(iii) heterometallic complexes. Variation of the degree of fluorination in the cyclometalating ligands coordinated to the Ir(iii) centres allows tuning of the photophysical properties and pure white light emission from a single complex. This journal is
Baschieri, Andrea,Muzzioli, Sara,Matteucci, Elia,Stagni, Stefano,Massi, Massimiliano,Sambri, Letizia
supporting information
p. 37 - 40
(2015/02/18)

Transamidation of carboxamides catalyzed by Fe(III) and water
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
p. 4544 - 4552
(2014/06/09)

An eco-friendly n-formylation of amines using nano cerium oxide as a recyclable catalyst under solvent-free and ultrasound irradiation conditions at room temperature
A new method for the synthesis of formamides has been developed by the N-formylation of amines with formic acid in the presence of nano cerium oxide as an efficient and recyclable catalyst under ultrasound irradiation. The reaction system is remarkably simple and environmentally benign.
Sajadi, S. Mohammad,Maham, Mehdi,Rezaei, Akbar
p. 49 - 54
(2014/03/21)

Nano CoFe2O4 as a magnetically separable catalyst for the solvent-free synthesis of formamides under ultrasound irradiation at room temperature
Formamides were efficiently synthesized from N-formylation of amines using CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst under ultrasound irradiation. The main advantages allocated to this method are chemoselectivity, reduced reaction times, high yields, magnetically recyclable catalyst, non-solvent green conditions and simple work-up procedure.
Bahari, Siavash
p. 532 - 537
(2013/08/23)

Toward the design of LPEI containing block copolymers: Improved synthesis protocol, selective hydrolysis, and detailed characterization
The synthesis of poly(2-ethyl-2-oxazoline)-b-linear poly(ethylenimine) (PEtOx-b-LPEI) copolymers by selective basic hydrolysis of PEtOx-b-poly(2-H-2- oxazoline) (PEtOx-b-PHOx) is described. For this purpose, an easy method for the preparation of the 2-H-2-oxazoline (HOx) monomer was developed. Based on the microwave-assisted polymerization kinetics for this monomer, PEtOx-b-PHOx copolymers were prepared. Subsequently, the block copolymers were selectively hydrolyzed to PEtOx-b-LPEI under basic conditions. The success of the polymerizations and subsequent post-polymerization reactions was demonstrated by 1H NMR spectroscopy and MALDI-TOF-MS investigations of the obtained polymers.
Tauhardt, Lutz,Kempe, Kristian,Schubert, Ulrich S.
p. 4516 - 4523,8
(2020/09/14)

Sulfated tungstate catalyzed highly accelerated N-formylation
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.
experimental part
p. 3259 - 3263
(2012/07/30)

An efficient method for N-formylation of amines using natural heu zeolite at room temperature under solvent-free conditions
A rapid and practical green route for N-formylation of primary and secondary amines with formic acid at room temperature under the solvent-free conditions using HEU zeolite as a heterogeneous, reusable and highly efficient catalyst is described. The process is remarkably simple and environmentally benign. Excellent chemoselectivity was observed for the conversion of primary amines in the presence of secondary amines.
Bahari, Siavash,Mohammadi-Aghdam, Babak,Sajadi, S. Mohammad,Zeidali, Fereshteh
experimental part
p. 2251 - 2254
(2012/08/28)

The dissociation chemistry of low-energy N-formylethanolamine ions: Hydrogen-bridged radical cations as key intermediates
Tandem mass spectrometry experiments show that N-formylethanolamine molecular ions HOCH2CH2NHC(H)O+ (FE1) lose C2H3O, CH2O and H2O to yield m/z 46 ions HC(OH)NH2+, m/z 59 ions CH2N(H)CHOH +, and m/z 71 N-vinylformamide ions CH2C(H)N(H)CHO +. A detailed mechanistic study using the CBS-QB3 model chemistry reveals that the readily generated 1,5-H shift isomer HOCHCH2N(H)C(H) OH+ (FE2) and hydrogen-bridged radical cations (HBRCs) act as key intermediates in a 'McLafferty + 1′ type rearrangement that yields the m/z 46 ions. The co-generated C2H3O neutrals are predicted to be vinyloxy radicals CH2CHO in admixture with CH3CO generated by quid-pro-quo (QPQ) catalysis. A competing C-C bond cleavage in FE1 leads to HBRC [CH2N(H)C(H)O-...H...OCH2] +, which serves as the direct precursor for CH2O loss. In addition, ion FE2 also communicates with a myriad of ion-molecule complexes of vinyl alcohol and formimidic acid whose components may recombine to form distonic ion FE3, HOCH(CH2)N(H)C(H)OH+, which loses H 2O after undergoing a 1,5-H shift. Further support for these proposals comes from experiments with D- and 18O-labelled isotopologues. Previously reported proposals for the H2O and CO losses from protonated N-formylethanolamine are briefly re-examined.
Jobst, Karl J.,Bowen, Richard D.,Terlouw, Johan K.
experimental part
p. 9 - 26
(2012/04/23)

Formylation of amines and alcohols using aminopropylated mesoporous SBA-15 silica (APMS) as an efficient and recyclable catalyst
Aminopropylated mesoporous SBA-15 silica (APMS) is introduced as a new, recyclable and efficient catalyst for the formylation of a variety of amines and alcohols by using readily available formic acid under solvent-free conditions.
Malakooti, Reihaneh,Sobhani, Sara,Razavi, Nasrin,Shafiei, Soheila,Mokhtari, Rezvan
experimental part
p. 1979 - 1990
(2012/04/17)

A convenient method for the N-formylation of amines at room temperature using TiO2-P25 or sulfated titania
Semiconductor catalyzed N-formylation of a variety of amines using formic acid as formylating agent has been investigated. Primary and secondary amines were found to react efficiently with formic acid in the presence of TiO 2-P25 or sulfated titania giving N-formyl derivatives in high yields at room temperature. Sulfated titania is found to be more efficient and reusable than TiO2-P25 for N-formylation of amines.
Krishnakumar,Swaminathan
scheme or table
p. 98 - 102
(2011/03/16)

Convenient N-formylation of amines in dimethylformamide with methyl benzoate under microwave irradiation
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Yang, Dongsik,Jeon, Heung Bae
scheme or table
p. 1424 - 1426
(2010/09/18)

Chiral isocyanoazides: Efficient bifunctional reagents for bioconjugation
Chiral scaffolds combining isocyanide and azide groups can be effectively synthesized to permit the efficient construction of both amino (hydroxy) acids and triazole derivatives, which enables the preparation of hybrid peptide molecules by Ugi/ click or click/Ugi strategies.
Nenajdenko, Valentine G.,Gulevich, Anton V.,Sokolova, Nadezhda V.,Mironov, Andrey V.,Balenkova, Elizabeth S.
scheme or table
p. 1445 - 1449
(2010/05/18)

Assessment of heat-sensitive thiophosphate protecting groups in the development of thermolytic DNA oligonucleotide prodrugs
Heat-sensitive thiophosphate protecting groups derived from the alcohol 4 or 10 have provided insights in the design of DNA oligonucleotide prodrugs. Indeed, functional groups stemming from the alcohol 9, 15, 16 or 22 may be applicable to thiophosphate protection of immunostimulatory CpG DNA motifs, whereas those originating from the alcohol 3, 5, 12, 13, 18, 20 or 22 offer adequate protection of terminal phosphodiester functions against ubiquitous exonucleases that may be found in biological environments. Functional groups derived from the alcohol 9, 15, 16, 19 or 23 are suitable for the protection of phosphodiester functions flanking the CpG motifs of immunomodulatory DNA sequences.
Ausín, Cristina,Kauffman, Jon S.,Duff, Robert J.,Shivaprasad, Shankaramma,Beaucage, Serge L.
experimental part
p. 68 - 79
(2010/03/04)

Indium-catalyzed N -formylation of amines under solvent-free conditions
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
experimental part
p. 1231 - 1234
(2010/07/08)

Solvent-free zinc-catalyzed amine N-formylation
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Kim, Joong-Gon,Jang, Doo Ok
experimental part
p. 2989 - 2991
(2012/04/17)

Facile and highly efficient N-formylation of amines using a catalytic amount of iodine under solvent-free conditions
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
experimental part
p. 2093 - 2096
(2010/10/03)

A very simple and highly efficient procedure for N-formylation of primary and secondary amines at room temperature under solvent-free conditions
N-Formylation of primary and secondary amines has efficiently been carried out at room temperature in excellent yields by using catalytic amount of sodium formate in formic acid under solvent-free conditions. The process is remarkably simple and environmentally benign.
Brahmachari, Goutam,Laskar, Sujay
experimental part
p. 2319 - 2322
(2010/05/19)

Formylation without catalyst and solvent at 80 °C
A simple and efficient protocol for N-formylation of aliphatic and heterocyclic amines has been described with formic acid in the absence of catalyst and solvent.
Rahman, Matiur,Kundu, Dhiman,Hajra, Alakananda,Majee, Adinath
experimental part
p. 2896 - 2899
(2010/06/14)

Corrigendum to "Formylation without catalyst and solvent at 80°C" (Tetrahedron Letters (2010) 51, (2896) DOI: 10.1016/j.tetlet. 2010.03.097)
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Rahman, Matiur,Kundu, Dhiman,Hajra, Alakananda,Majee, Adinath
scheme or table
p. 4584 - 4585
(2010/09/14)

A new and general method for the synthesis of tripeptide aldehydes based on the multi-component Ugi reaction
Tripeptide aldehydes, such as Z-Leu-Leu-Leu-H (MG-132), are an important class of compounds due to their biological activity. A new, general method for the synthesis of tripeptide aldehydes based on the multi-component Ugi reaction was developed. A careful choice of isocyanides makes it possible to obtain tripeptide precursors whose functionalization led to target structures. This method can be used for the preparation of tripeptide aldehydes with non-natural amino acid side chains.
Mroczkiewicz, Micha?,Ostaszewski, Ryszard
experimental part
p. 4025 - 4034
(2009/09/30)

Synthesis and catalytic properties of diverse chiral polyamines
Chiral polyamines can be utilized for a variety of potential applications, ranging from asymmetric catalysis to nonviral gene delivery systems for DNA and RNA. They can also be utilized to solubilize carbon nanotubes. Thus, methods for the straightforward synthesis of chiral polyamines are needed. We present herein two synthetic strategies for accessing chiral polyamines. The potential of these chiral amines to catalyze two organic reactions with a high degree of chiral induction was also explored.
Levine, Mindy,Kenesky, Craig S.,Zheng, Shengping,Quinn, Jordan,Breslow, Ronald
p. 5746 - 5750
(2008/12/22)

ZnO as a new catalyst for N-formylation of amines under solvent-free conditions
The treatment of amines with formic acid in the presence of ZnO under solvent-free conditions brings about highly and efficient N-formylation to give the corresponding formamides in excellent yields. The N-formylation reaction not only involves mild conditions, simple operation, and high yields but also high chemoselectivity.
Hosseini-Sarvari, Mona,Sharghi, Hashem
p. 6652 - 6654
(2007/10/03)

Synthesis of N-vinyl formamide
A process to produce N-vinylformamide includes the steps of: reacting hydroxyethyl formamide with a reactant comprising at least one cyclic anhydride group to form an ester, and dissociating the ester via heat in a thin film evaporation to synthesize N-vinylformamide and a compound comprising at least one diacid group, the N-vinylformamide separating from the diacid during the thin film evaporation. The reactant including at least one cyclic anhydride group can, for example, be succinic anhydride, maleic anhydride, phthalic anhydride, (2-docecen-1-yl)succinic anhydride, exo-3,6-epoxy-1,2,3,6 -tetrahydrophthalic anhydride or a polymer including at least one cyclic anhydride group. A process to produce N-vinylformamide comprises the steps of: mixing acetaldehyde, formamide and a source of anhydride in a single reaction vessel, reacting the acetaldehyde, formamide and the source of anhydride in the reaction vessel under pressure, dissociating an ester formed by a reaction between the source of anhydride and hydroxyethyl formamide formed in the reaction vessel to synthesize N-vinylformamide and a compound comprising at least one diacid group.
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(2008/06/13)

USE OF CERTAIN N-ACYLETHANOLAMINES TO ACHIEVE ETHYLENE- AND CYTOKININ-LIKE EFFECTS IN PLANTS AND FUNGI
N-acylethanolamines (NAEs) that can deliver an ethylene- or cytokinin-like effects to a plant, plant part or fungus are disclosed. Also disclosed are methods of using the NAES.
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Page 7

(2010/11/30)

Synthesis of tetrazolopiperazine building blocks by a novel multi-component reaction
A novel Ugi-five-centre-four-component reaction (U-5C-4CR) of aldehydes, primary amines, trimethylsilylazide and 2-isocyanoethyltosylate yielding tetrazolopiperazine building blocks is described.
Umkehrer, Michael,Kolb, Jürgen,Burdack, Christoph,Ross, Günther,Hiller, Wolfgang
p. 6421 - 6424
(2007/10/03)

Formyloxy-acetonitrile - A reagent for convenient N- and O-formylations
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Deutsch,Duczek,Niclas
p. 488 - 490
(2007/10/03)

Reaction of (Vinyloxyalkyl)amines with Chloral Hydrate
Reaction of (2-vinyloxyethyl)amine with chloral hydrate produces unstable 2,2,2-trichloro-1-ethanol, which is cleaved to give N-(2-vinyloxyethyl)formamide.The latter undergoes cyclization into thermodynamically more stable 3-formyl-2-methyl-1,3-oxazolidine during isolation.Similar cyclic and linear formamides were obtained from chlral hydrate and other vinyl-substituted 1,2-, 1,3-, and 1,4-aminoalcohols.N-(Hydroxyalkyl)-formamides were isolated as by-products.
Kukharev, B. F.,Stankevich, V. K.,Klimenko, G. R.
p. 591 - 596
(2007/10/03)

A convenient procedure for the formylation of amines and alcohols using cyanomethyl formate
A simple metyod for the direct formylation of amines using cyanomethyl formate is described. The formylation succeeds in moderate to high yields under mild and neutral conditions. Thus, formamides 2a-f, 2i-m are obtained at room temperature. A chemoselective N-formylation is achieved in the case of ethanolamine. The formylation of nitroanilines and the O-formylation of alcohols only succeeds in the presence of a catalytic amount of imidazole leading to 2g,h and 3a-e, respectively.
Deutsch,Niclas
p. 1561 - 1568
(2007/10/02)

N-Formylation of Aliphatic Primary Amines with N,N-Dimethylformamide Promoted by 2,3-Dihydro-1,4-naphthalazinedione
The N-formylation of aliphatic primary amine proceeded very effectively in N,N-dimethylformamide in the presence of restorable 2,3-dihydro-1,4-naphthalazinedione.
Iwata, Masaaki,Kuzuhara, Hiroyoshi
p. 2029 - 2030
(2007/10/02)

Research on radioprotective agents: Δ-2 Thiazolines and homologous derivatives
Compounds derived from Δ-2 thiazoline, Δ-2 thiazolinium iodoalkylate and 4,5-dihydro-1,3 thiazine have been prepared and evaluated as potential antiradiation agents in mice. They generally have a low toxicity and significant radioprotective activity.
Robbe,Fernandez,Chapat,et al.
p. 16 - 24
(2007/10/02)