75996-27-9Relevant academic research and scientific papers
Synthesis of Urea Derivatives from CO2 and Silylamines
Xu, Maotong,Jupp, Andrew R.,Ong, Maegan S. E.,Burton, Katherine I.,Chitnis, Saurabh S.,Stephan, Douglas W.
supporting information, p. 5707 - 5711 (2019/04/16)
A series of thirty-three N,N′-diaryl, dialkyl, and alkyl-aryl ureas have been prepared in pyridine or toluene by reaction of silylamines with CO2. This protocol is shown to provide facile access to 13C-labeled ureas, as well as chiral and macrocyclic ureas. These reactions proceed through initial generation of the corresponding silylcarbamates, which subsequently react with silylamine under thermal conditions to afford the thermodynamically favored urea and disilyl ether.
Stoichiometric Reactions of CO2 and Indium-Silylamides and Catalytic Synthesis of Ureas
Xu, Maotong,Jupp, Andrew R.,Stephan, Douglas W.
supporting information, p. 14277 - 14281 (2017/10/31)
The indium compounds In(N(SiMe3)2)2Cl?THF (2) and In(N(SiMe3)2)Cl2?(THF)n (3) were shown to react with CO2 to give [(Me3Si)2N)InX(μ-OSiMe3)]2 (X=N(SiMe3)2 4, Cl 5). 0.05–2.0 mol % of the species 3 acts as a pre-catalyst for the conversion of aryl and alkyl silylamines under CO2 (2–3 atm) to give the corresponding ureas in 70–99 % yields. A proposed mechanism is supported by experimental and computational data.
Synthesis of 3-(4-methoxyphenyl)-5,7-dimethoxy-(1H)-quinolin-2- or 4-ones and derivatives
Croisy, Martine,Huel, Christiane,Bisagni, Emile
, p. 683 - 690 (2007/10/03)
Condensation of ethyl 2-(4-methoxyphenyl)-3-hydroxyacrylate with 3,5-dimethoxyaniline afforded, depending on experimental conditions, either 3-(4-methoxyphenyl)-5,7-dimethoxy-(1H)-quinolin-2-one or 3-(4-methoxyphenyl)-5,7-dimethoxy-(1H)-quinolin-4-one. Whereas chlorination with phosphorous oxychloride led to the corresponding 2- and 4- chloroquinolines derivatives, 2-chloro-3-(4-methoxyphenyl)-5,7-dimethoxyquinoline was also obtained by using the Meth Cohn method's.
Long-chain Phenols. Part 16. A Novel Synthesis of Homologous Orsellinic Acids and their Methyl Ethers
Durrani, Aziz A.,Tyman, John H. P.
, p. 1658 - 1666 (2007/10/02)
By the novel reaction of 3,5-dimethoxyfluorobenzene with n-alkyl-lithium compounds, followed by carbonation, homologous orsellinic acid dimethyl ethers (6-alkyl-2,4-dimethoxybenzoic acids) have been obtained.The reactions proceeded best with the homologues of methyl-lithium.These reactions are considered to occur by way of 3,5-dimethoxybenzyne. 2,4-Dimethoxyfluorobenzene did not form an aryne but gave 3-fluoro-2,6-dimethoxybenzoic acid instead.Decomposition with water of alkyl-lithium reaction mixtures from 3,5-dimethoxyfluorobenzene yielded 5-n-alkylresorcinol dimethyl ethers.Demethylaton of 6-alkyl-2,4-dimethoxybenzoic acids with boron trichloride proceeded partially and selectively to give the 6-alkyl-2-hydroxy-4-methoxybenzoic acids, and completely with aluminium chloride to give the homologous orsellinic acids.Boron tribromide was less effective, but readily gave the 5-alkyl resorcinols from the corresponding dimethyl ethers.
