100-74-3Relevant articles and documents
Novel Synthesis of Carbamic Ester from Carbon Dioxide, Amine, and Ortho Ester
Ishii, Shideru,Nakayama, Hidenobu,Yoshida, Yasuhiko,Yamashita, Tadataka
, p. 455 - 458 (1989)
Carbon dioxide reacted with aliphatic amines and ortho esters to form carbamic esters in good yields.The influence of different ortho esters on the carbamate synthetic reaction is described.In the case of orthocarbonates, carbamic esters were obtained in high yields.The reaction of carbon dioxide, amines, and ortho esters may involve a competitive reaction between the esterification of carbamic acid produced by a reaction of carbon dioxide with amine, and the alkylation of amine.
Mild Hydrogenation of Amides to Amines over a Platinum-Vanadium Bimetallic Catalyst
Mitsudome, Takato,Miyagawa, Kazuya,Maeno, Zen,Mizugaki, Tomoo,Jitsukawa, Koichiro,Yamasaki, Jun,Kitagawa, Yasutaka,Kaneda, Kiyotomi
, p. 9381 - 9385 (2017)
Hydrogenation of amides to amines is an important reaction, but the need for high temperatures and H2 pressures is a problem. Catalysts that are effective under mild reaction conditions, that is, lower than 30 bar H2 and 70 °C, have not yet been reported. Here, the mild hydrogenation of amides was achieved for the first time by using a Pt-V bimetallic catalyst. Amide hydrogenation, at either 1 bar H2 at 70 °C or 5 bar H2 at room temperature was achieved using the bimetallic catalyst. The mild reaction conditions enable highly selective hydrogenation of various amides to the corresponding amines, while inhibiting arene hydrogenation. Catalyst characterization showed that the origin of the catalytic activity for the bimetallic catalyst is the oxophilic V-decorated Pt nanoparticles, which are 2 nm in diameter.
The Me3Si Substituent Effect on the Reactivity of Silanes. Structural Correlations between Silyl Radicals and Their Parent Silanes
Chatgilialoglu, C.,Guerrini, A.,Lucarini, M.
, p. 3405 - 3409 (1992)
Good linear correlations exist both between the bond dissociation energy of an Si-H bond and the corresponding SiH stretching frequency and between the (29)Si hyperfine splitting of a silicon-centered radical and J((29)Si-H) for the corresponding silane, when the successive substitution at the Si-H function takes place inside a family, i.e., (Me3Si)3-nSi(H)Men, n = 0-3.Explanations for these phenomena are advanced.Such structural correlations allow the characterization of (Me3Si)2Si(H)Me as a radical-based reducing agent with low hydrogen-donating abilities.Rate constants for the reaction of primary alkyl radicals with (Me3Si)2Si(H)Me have been measured over a range of temperatures by using competing unimolecular radical reactions as timing devices.The radical trapping abilities of this silane and other common radical-based reducing agents are compared.
Leishmanicidal potential of N-substituted morpholine derivatives: Synthesis and structure-activity relationships
Khan, Khalid Mohammed,Khan, Muhammad Zarrar,Taha, Muhammad,Maharvi, Ghulam Murtaza,Saify, Zafar Saeed,Parveen, Shahnaz,Choudhary, Muhammad Iqbal
, p. 479 - 484 (2009)
A series of N-substituted morpholines 2-20 was synthesised by reacting various acid chlorides and alkyl halides with morpholine (1). All of the synthesised compounds 2-20 were screened for their leishmanicidal effects using amphotericin B (IC50 = 0.24 μg L-1) and pentamidine (IC50 = 2.56 μg mL-1) as standards and a structure-activity relationship (SAR) study was established. The compounds 2 (IC50 = 48 μg mL-1), 3 (IC50 = 30.0 μg mL-1), 10 (IC50 = 41.0 μg mL-1), 15 (IC50 = 33.0 μg mL-1), 16 (IC50 = 35.0 μg mL-1) and 20 (IC50 = 47.0 μg mL-1) showed weak leishmanicidal activities.
Selective Synthesis of Secondary and Tertiary Amines by Reductive N-Alkylation of Nitriles and N-Alkylation of Amines and Ammonium Formate Catalyzed by Ruthenium Complex
Alshakova, Iryna D.,Nikonov, Georgii I.
, p. 5370 - 5378 (2019)
A new ruthenium catalytic system for the syntheses of secondary and tertiary amines via reductive N-alkylation of nitriles and N-alkylation of primary amines is proposed. Isomeric complexes 8 catalyze transfer hydrogenation and N-alkylation of nitriles in ethanol to give secondary amines. Unsymmetrical secondary amines can be produced by N-alkylation of primary amines with alcohols via the borrowing hydrogen methodology. Aliphatic amines were obtained with excellent yields, while only moderate conversions were observed for anilines. Based on kinetic and mechanistic studies, it is suggested that the rate determining step is the hydrogenation of intermediate imine to amine. Finally, ammonium formate was applied as the amination reagent for alcohols in the presence of ruthenium catalyst 8. Secondary amines were obtained from primary alcohols within 24 hours at 100 °C, and tertiary amines can be produced after prolonged heating. Secondary alcohols can only be converted to secondary amines with moderate yield. Based on mechanistic studies, the process is suggested to proceed through an ammonium alkoxy carbonate intermediate, where carbonate acts as an efficient leaving group.
In situ DRIFTS study on the synthesis of N-alkylmorpholines
Luo, Chenxi,Luo, Hu,Qian, Chao,Chen, Yunbin,Feng, Lie,Chen, Xinzhi
, p. 2825 - 2835 (2013)
In situ diffuse reflectance Fourier-transform infrared spectroscopy was used to perform mechanistic investigation on the synthesis of N-alkylmorpholines from diethylene glycol (DEG), alcohol and ammonia. The results showed that the synthesis of N-alkylmorpholines on a heterogeneous catalyst proceeded along the reaction path between DEG and alkylamine when choosing CuO-NiO/γ-Al 2O3 as a suitable catalyst. In addition, the yield of methylmorpholine and ethylmorpholine was 86.4 and 76.6 %, respectively.
SYNTHESIS OF NITROGEN-CONTAINING HETEROCYCLES OF AN IRON CATALYST. 2. THE CONVERSIONS OF 1,4-BUTANEDIOL AND DIETHYLENEGLYCOL IN THE PRESENCE OF AMMONIA AND HYDROGEN
Kliger, G. A.,Lesik, O. A.,Marchevskaya, E. V.,Mikaya, A. I.,Zaikin, V. G.,et al.
, p. 161 - 164 (1987)
The gas-phase interaction of 1,4-butanediol and diethylene glycol with ammonia and/or hydrogen on a reduced, fused, iron catalyst has been investigated.
Mild N-Alkylation of Amines with Alcohols Catalyzed by the Acetate Ru(OAc)2(CO)(DiPPF) Complex
Figliolia, Rosario,Baldino, Salvatore,Nedden, Hans G.,Zanotti-Gerosa, Antonio,Baratta, Walter
, p. 14416 - 14419 (2017)
The acetate complex Ru(OAc)2(DiPPF) (2) obtained from Ru(OAc)2(PPh3)2 (1) and 1,1′-bis(diisopropylphosphino)ferrocene (DiPPF) reacts cleanly with formaldehyde affording Ru(OAc)2(CO)(DiPPF) (3) in high yield. The monocarbonyl complex 3 (0.4-2 mol %) efficiently catalyzes the N-alkylation of primary and secondary alkyl and aromatic amines using primary alcohols ROH (R=Et, nPr, nBu, PhCH2) under mild reaction conditions (30–100 °C) with an alcohol/amine molar ratio of 10-100. Formation of the monohydride RuH(OAc)(CO)(DiPPF) (4) has been observed by reaction of 3 with iPrOH in the presence of NEt3 at RT through an equilibrium reaction.
Hydrogenation of amides by the use of bimetallic catalysts consisting of group 8 to 10, and group 6 or 7 metals
Hirosawa, Chitaru,Wakasa, Noriko,Fuchikami, Takamasa
, p. 6749 - 6752 (1996)
Hydrogenation of amides can be catalyzed by bimetallic systems, which consist of Group 8 to 10 late transition-metals and Group 6 or 7 early transition-metals, under the mild conditions to afford the corresponding amines selectively in good to excellent yields.
Ionic liquid/H2O-mediated synthesis of mesoporous organic polymers and their application in methylation of amines
Yu, Xiaoxiao,Yang, Zhenzhen,Zhang, Hongye,Yu, Bo,Zhao, Yanfei,Liiu, Zhenghui,Ji, Guipeng,Liu, Zhimin
, p. 5962 - 5965 (2017)
Mesoporous Tr?ger's base-functionalized polymers (Meso-TBPs) were prepared using a sulfonic acid group functionalized ionic liquid/H2O system, with surface areas up to 431 m2 g-1 and pore sizes of 3-15 nm. Ir(ii) coordinated Meso-TBPs exhibited extraordinary catalytic performance in the N-methylation of amines using methanol.
