103723-70-2Relevant articles and documents
Efficient synthesis of oxazolidin-2-one via (chitosan-Schiff base)cobalt(II)-catalyzed oxidative carbonylation of 2-aminoalkan-1-ols
Liu, Jianming,Sun, Wei,Zheng, Shuzhan,Xia, Chungu
, p. 1593 - 1598 (2007)
The (chitosan-Schiff base)cobalt(II) complex was found to be an efficient catalyst for the oxidative carbonylation (CO/O2) of 2-aminoalkan-1-ols 1 to give oxazolidin-2-ones 2, in the presence of NaI. The effects of promoters, temperature, solvents, and other reaction conditions were investigated in this study.
An improved procedure for the palladium-catalyzed oxidative carbonylation of β-amino alcohols to oxazolidin-2-ones
Gabriele, Bartolo,Mancuso, Raffaella,Salerno, Giuseppe,Costa, Mirco
, p. 601 - 604 (2003)
A highly efficient oxidative cyclocarbonylation of β-amino alcohols and 2-aminophenol to oxazolidin-2-ones has been achieved by using PdI2 in conjunction with KI as the catalytic system in DME under relatively mild conditions (100 °C and 20 atm of a 4:1 mixture of CO and air).
Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates
Casiello, Michele,Iannone, Francesco,Cotugno, Pietro,Monopoli, Antonio,Cioffi, Nicola,Ciminale, Francesco,Trzeciak, Anna M.,Nacci, Angelo
, p. 8 - 14 (2015)
Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100°C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.
Simple preparation method of N-acyl compound
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Paragraph 0049-0051, (2019/07/04)
The invention relates to a simple preparation method of an N-acyl compound. The simple preparation method comprises the specific steps that an amine compound and R-OCF3 are mixed in a solvent and react for 1 min-48 h at -80-100 DEG C, after the reaction is completed, water is added for quenching, and column separation and purification or recrystallization and purification are carried out to obtainthe N-acyl compound. According to the simple preparation method of the N-acyl compound, the characteristic that a substance containing trifluorooxygen groups can be decomposed in situ to produce fluorophosgene is utilized, and the substance directly reacts with the amine compound to achieve rapid N-carbonylation of an amines substrate and efficiently prepare a urea derivative and a carbamyl fluoride compound. The simple preparation method of the N-acyl compound has the advantages that the operation is simple, the reaction time is short, the application range of the substrate is wide, no catalysts or additives need to be used, the raw materials are easy to obtain, the product yield is high, the purification is easy, and the required compound can be obtained by using a column chromatographyisolation method or recrystallization.
Concise and Additive-Free Click Reactions between Amines and CF3SO3CF3
Song, Hai-Xia,Han, Zhou-Zhou,Zhang, Cheng-Pan
supporting information, p. 10907 - 10912 (2019/08/02)
Trifluoromethyl trifluoromethanesulfonate has proved to be an excellent reservoir of difluorophosgene and a promising click ligation for amines in the preparation of urea derivatives, heterocycles, and carbamoyl fluorides under metal- and additive-free conditions. The reactions are rapid, efficient, selective, and versatile, and can be performed in benign solvents, giving products in excellent yields with minimal efforts for purification. The characteristics of the reactions meet the requirements of a click reaction. The use of trifluoromethyl trifluoromethanesulfonate as a click reagent is advantageous over other “CO” sources (e.g., TsOCF3, PhCO2CF3, CsOCF3, AgOCF3, and triphosgene) because this reagent is readily accessible; easy to scale up; and highly reactive, even under metal- and additive-free conditions. It is anticipated that CF3SO3CF3 will be increasingly as important as SO2F2 as a click agent in future drug design and development.
Synthesis of some 2-Oxazolidinones in mild conditions
Bratulescu, George
experimental part, p. 929 - 930 (2011/12/15)
One step efficient protocol for the synthesis of 2-oxazolidinones in paste chemical medium is described under microwave activation with 80 % yield.
Synthesis of 2-oxazolidinones by salen-Co-complexes catalyzed oxidative carbonylation of β-amino alcohols
Liu, Jian-Ming,Peng, Xin-Gao,Liu, Jian-Hua,Zheng, Shu-Zhan,Sun, Wei,Xia, Chun-Gu
, p. 929 - 932 (2008/02/04)
2-Oxazolidinones are synthesized in high yield by oxidative carbonylation of β-amino alcohols using salen-Co(II)/NaI or salen-Co(III)-I as a catalyst and using CO as the carbonyl source. Studies of functional group compatibility using a series of substituted salen-Co(II) or salen-Co(III)-I complexes demonstrate a broad tolerance of functionality during the carbonylation reaction.
Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation
Birman, Vladimir B.,Jiang, Hui,Li, Ximin,Guo, Lei,Uffman, Eric W.
, p. 6536 - 6537 (2007/10/03)
Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright
Synthesis of 2-oxazolidinone catalyzed by palladium on charcoal: A novel and highly effective heterogeneous catalytic system for oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol
Li, Fuwei,Xia, Chungu
, p. 542 - 546 (2007/10/03)
Oxidative cyclocarbonylation of β-aminoalcohols and 2-aminophenol to synthesize corresponding 2-oxazolidinones catalyzed by a Pd/C-I2 heterogeneous catalytic system has been developed which gave excellent selectivity and high turnover frequency (TOF) values 15 times larger than the best results previously reported. The catalyst could be reused for five times almost without losing its catalytic activity and selectivity. The effects of promoters, pretreatment, solvents, and reaction conditions have been investigated.
Mechanistic study on nitrosation-deaminocyclization of mono-carbamoylated vicinal amino alcohols and diols: a new preparative in situ formation of ethanediazo hydroxide for the ethylation of carboxylates under mild conditions
Suzuki, Masumi,Sugai, Takeshi
, p. 1217 - 1228 (2007/10/03)
While the cyclization of N-carbamoylamino alcohols into oxazolidinones via the activation with NO(1+) underwent smoothly, we found that similar reactions of vicinal diol monocarbamates were very slow. Mechanistic studies by means of time-resolved IR measurements of the former reaction suggested that the initial O-nitrosation was the rate-determining step. Indeed, the introduction of an ethyl group on the nitrogen terminus of diol monocarbamate promoted the desired cyclic carbonate formation. The concomitantly formed ethanediazo hydroxide, the precursor of the protonated form of diazoethane, was evidenced by trapping with p-nitrobenzoic acid as an ethyl ester. The formation of ethyl ester accelerates the reaction in an irreversible manner. Based on an elaboration of the substrates and reaction conditions, 2,3-dimethyl-2,3-butanediol mono-N-ethyl-N-nitrosocarbamate, which is easily prepared in situ from the corresponding ethylcarbamate and t-butyl nitrite, was developed as a new ethylation reagent of various carboxylic acids under mild conditions.
