103-70-8Relevant articles and documents
Mesoporous silica SBA-15 functionalized with acidic deep eutectic solvent: A highly active heterogeneous N-formylation catalyst under solvent-free conditions
Azizi, Najmedin,Edrisi, Mahtab,Abbasi, Faezeh
, (2018)
Mesoporous silica SBA-15 functionalized with N-methylpyrrolidonium-zinc chloride based deep eutectic solvent (DES) is found to be a more efficient and reusable catalyst for a convenient N-formylation of a variety of amines at room temperature. N-Formylation of primary, secondary as well as heterocyclic amines have been carried out in good to excellent yields by treatment with formic acid in low loading of DES/SBA-15 an environmentally benign catalyst for the first time. The DES/SBA-15 catalyst, which possesses both Br?nsted and Lewis acidities as well as an active SBA-15 support, makes this procedure quite simple, reusable, more convenient and practical. This catalyst was tolerant of a wide range of functional groups, and it can be reused for four runs without obvious deactivation.
N-Formylbenzotriazole: A stable and convenient N- and O-formylating agent
Katritzky,Chang,Yang
, p. 503 - 505 (1995)
N-Formylbenzotriazole, prepared by the reaction of benzotriazole and formic acid in the presence of dicyclohexylcarbodiimide, is demonstrated to be a superior N- and O-formylating agent.
Engineering Porphyrin Metal-Organic Framework Composites as Multifunctional Platforms for CO2Adsorption and Activation
Liu, Jiewei,Fan, Yan-Zhong,Zhang, Kun,Zhang, Li,Su, Cheng-Yong
, p. 14548 - 14556 (2020)
As an effective solution toward the establishment of a sustainable society, the reductive transformation of CO2 into value-added products is certainly important and imperative. Herein, we report a porphyrin metal-organic framework composite Au@Ir-PCN-222, which is obtained through the in situ formation of Au nanoparticles in the coordination interspaces of Ir-PCN-222. Catalytic results show that Au@Ir-PCN-222 is highly efficient for CO2 reduction and aminolysis, giving rise to formamides in high yields and selectivities under room temperature and atmospheric pressure. Mechanistic studies disclose that the high efficiency of Au@Ir-PCN-222 is due to the synergistic catalysis of Au NPs and Ir-PCN-222, in which Au NPs can adsorb CO2 molecules on their surfaces and then increase the CO2 concentration in the cavities of the framework, and at the same time, Au NPs transfer electrons to Ir-porphyrin units and therefore increase the interactions with CO2 molecules.
Mild and convenient N-formylation protocol in water-containing solvents
Aleiwi, Bilal A.,Mitachi, Katsuhiko,Kurosu, Michio
, p. 2077 - 2081 (2013)
We have realized that N-formylations of free amines of some drug leads can improve PK/PD property of parent molecules without decreasing their biological activities. In order to selectively formylate primary amines of polyfunctional molecules, we have sought a mild and convenient formylation reaction. In our screening of N-formylation of an α-amino acid, l-phenylalanine, none of formylation conditions reported to date yielded the desired HCO-l-Phe-OH with satisfactory yield. N-formylations of amino acids with HCO2H require a water-containing media and suppress polymerization reactions due to the competitive reactions among carboxylic acids. We found that N-formylations of α-amino acids could be achieved with a water-soluble peptide coupling additive, an Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl-2-cyano-2- (hydroxyimino)acetate (2), EDCI, and NaHCO3 in water or a mixture of water and DMF system, yielding N-formylated α-amino acids with excellent yields. Moreover, these conditions could selectively formylate primary amines over secondary amines at a controlled temperature. A usefulness of these conditions was demonstrated by selective formylation of daptomycin antibiotic which contains three different amino groups.
Building N-Heterocyclic Carbene into Triazine-Linked Polymer for Multiple CO2 Utilization
Yue, Chengtao,Wang, Wenlong,Li, Fuwei
, p. 5996 - 6004 (2020)
The development of new CO2 detection technologies and CO2 “capture-conversion” materials is of great significance due to the growing environmental crisis. Here, multifunctional triazine-linked polymers with built-in N-heterocyclic carbene (NHC) sites (designated as NHC-triazine@polymer) are presented for simultaneous CO2 detection, capture, activation, and catalytic conversion. NHC-triazine@polymer were readily obtained through polymerization of cyanophenyl-substituted NHC. The obtained film-like polymers exhibited interesting CO2-triggered fluorescence “turn-on” response and CO2-sensitive reversible color change. Both NHC and triazine sites could act as efficient binding sites for CO2, and the CO2 uptake of NHC and triazine reached 1.52 and 1.36 mmol g?1, respectively. Notably, after being captured by NHC, CO2 was activated into a zwitterionic adduct NHC?CO2 that could be easily transformed into cyclic carbonate in the presence of epoxides. Moreover, NHC-triazine@polymer were stable and active catalysts for the conversion of low-concentration CO2 in a gas mixture (7 vol %) into cyclic carbonates as well as for hydrosilylation of CO2 to formamides.
Synthesis of Substituted Thioamides from gem-Dibromoalkenes and Sodiumsulfide
Morri, Ashok K.,Thummala, Yadagiri,Adepu, Ramesh,Sharma, Gangavaram V. M.,Ghosh, Subhash,Doddi, Venkata Ramana
, p. 7159 - 7163 (2019)
A three-component reaction of 1,1-dibromoalkenes, sodium sulfide, and N-substituted formamide for the synthesis of disubstituted thioamides has been developed. Various dibromoalkenes were found to be compatible under these conditions and gave corresponding thioamides in good to excellent yields.
Iridium-Catalyzed Direct Amidation of Imidazoles at the C-2 Position with Isocyanates in the Presence of Hydrosilanes Leading to Imidazole-2-Carboxamides
Fukumoto, Yoshiya,Shiratani, Motohiro,Noguchi, Hikaru,Chatani, Naoto
, p. 3011 - 3018 (2021)
Regioselective coupling reaction of N -substituted imidazoles with isocyanates in the presence of a stoichiometric amount of hydrosilanes catalyzed by Ir 4(CO) 12to give imidazole-2-carboxamides is reported. Imidazoles bearing an (O -silyl)carboximidate group at the 2-position appear to be initially formed in the reaction; these are then hydrolyzed to the final products in situ. The addition of the hydrosilane was essential for the catalytic reaction to proceed. Substituents on the imidazole ring had no effect on the reaction, except for certain bulky substituents such as tBu and Ph groups at the 4-position. Triazoles such as 4-methyl-4 H -1,2,4-triazole and 1-methyl-1 H -1,2,4-triazole were also applicable to this C-H amidation, and the latter reaction proceeded regioselectively at the carbon atom between the sp 3and sp 2nitrogen atoms of the ring, and not between the two sp 2nitrogen atoms.
A simple method for preparation of ZnO nanoparticles as a highly efficient nanocatalyst for N-formylation of primary and secondary amines under solvent-free condition
Alinezhad, Heshmatollah,Salehian, Fatemeh
, p. 532 - 538 (2013)
A convenient reaction between alky, aryl, and heteroalkyl amines and formic acid as a formylating agent in the presence of catalytic amount of mechanochemically synthesized zinc oxide nanoparticles under solvent-free condition for the synthesis of corresponding N-formyl derivatives is described. Copyright Taylor and Francis Group, LLC.
Co3O4 nanoparticles prepared by oxidative precipitation method: an efficient and reusable heterogeneous catalyst for N-formylation of amines
Marjani, Ahmad Poursattar,Hosseini, Seyed Ali,Shokri, Zahra,Maleki, Nasim
, p. 413 - 422 (2017)
Abstract: N-formylation of different amines was carried out with formic acid in the presence of the Co3O4 nanoparticles as an efficient, stable heterogeneous catalyst to give the corresponding formamides under solvent-free conditions. This method has advantages over the reported methods such as high yields, mild conditions, easy work-up and short reaction times. The catalyst was characterized by different techniques such as XRD, SEM and FT-IR spectroscopy. Graphical Abstract: [Figure not available: see fulltext.]
Highly efficient rhodium-catalyzed transfer hydrogenation of nitroarenes into amines and formanilides
Wei, Yawen,Wu, Jianjun,Xue, Dong,Wang, Chao,Liu, Zhaotie,Zhang, Zhuozhuo,Chen, Guangfu,Xiao, Jianliang
, p. 1295 - 1298 (2014)
An efficient and selective rhodium-catalyzed transfer hydrogenation of nitroarenes with formic acid as the hydrogen source to give amines or formanilides has been developed. The addition of iodide ion accelerates the reaction, which can take place at room temperature. Georg Thieme Verlag Stuttgart New York.
