935-06-8Relevant academic research and scientific papers
Synergetic activation of CO2by the DBU-organocatalyst and amine substrates towards stable carbamate salts for synthesis of oxazolidinones
Chen, Xiao-Chao,Liu, Ye,Lu, Yong,Yao, Yin-Qing,Zhao, Kai-Chun
, p. 7072 - 7082 (2021/11/17)
The development of an efficient methodology to transform CO2 into valuable chemicals has attracted increasing attention concerning the challenging issues of CO2-utilization. Herein, an efficient approach for the preparation of oxazolidinones from CO2, primary (aliphatic/aromatic) amines and 1,2-dichloroethane (or its derivatives) catalyzed by DBU organo-superbase was achieved with yields of 47-97% under mild conditions (80-100 °C, 12 h, 1.0 MPa CO2). Control experiments demonstrated that the formation of an ion-pair carbamate salt intermediate IS-B derived from the reaction of CO2, DBU (catalyst) and an amine (substrate) was the key step for this three-component reaction. The available DBU-amine-CO2 adduct intermediate (like IS-B-2) with fair stability will evolve into the thermodynamically stable product oxazolidinones upon attack of 1,2-dichloroethane (or its derivatives), along with the regeneration of the DBU catalyst. Alternatively, the decomposition of the DBU-aryl amine-CO2 adduct (like IS-B-1) with relatively poor stability also could result in the competitive substitution reaction of 1,2-dichloroethane (or its derivatives) with the aryl amine. This work provides insights into synergetic CO2-activation by the DBU-catalyst and a nucleophilic amine-substrate via the formation of robust carbamate salt intermediates responsible for the final production of oxazolidinones. This journal is
Synthesis of Oxazolidinones and Derivatives through Three-Component Fixation of Carbon Dioxide
Mei, Congmin,Zhao, Yibo,Chen, Qianwei,Cao, Changsheng,Pang, Guangsheng,Shi, Yanhui
, p. 3057 - 3068 (2018/06/04)
An effective three-component fixation of atmospheric CO2 with readily available 1,2-dichloroethane and aromatic amine toward oxazolidinones catalyzed by in situ NHC was developed. The reaction occurred in good to excellent yields with good gene
Potassium iodide catalysed monoalkylation of anilines under microwave irradiation
Romera, Juan L.,Cid, José M.,Trabanco, Andrés A.
, p. 8797 - 8800 (2007/10/03)
A potassium iodide catalysed method for the selective N-monoalkylation anilines with alkylhalides and alkyltosylates under microwave irradiation is described. The corresponding N-alkylanilines are obtained in good yields with only minor quantities of dialkylation by-products.
A HIGHLY EFFICIENT AND GENERAL N-MONOMETHYLATION OF FUNCTIONALIZED PRIMARY AMINES VIA FORMYLATION -- BORANE:METHYL SULFIDE REDUCTION
Krishnamurthy, S.
, p. 3315 - 3318 (2007/10/02)
Formylation of functionalized primary aromatic and aliphatic amines with acetic formic anhydride (AFA) followed by borane:methyl sulfide reduction in the same pot affords the corresponding N-methylamines in excellent isolated yields, uncontaminated by bis alkylation; the reaction sequence is applicable to even very weakly basic and sterically hindered amines.
Cyclic carbamates as reagents for alkylamination of aromatic derivatives under friedel-crafts conditions
Jouitteau,Perchec,Forestiere,Silicon
, p. 1719 - 1722 (2007/10/02)
Aryl(ethyl-) and propylamines are obtained with good yields by a decarboxylation-alkylation process applied on aluminium trichloride-cyclic carbamate complexes. The coupling of two aromatic units is observed in the case of oxazolidinonetoluene reaction.
