2739-05-1Relevant academic research and scientific papers
N-Methylation and Trideuteromethylation of Amines via Magnesium-Catalyzed Reduction of Cyclic and Linear Carbamates
Magre, Marc,Szewczyk, Marcin,Rueping, Magnus
supporting information, p. 3209 - 3214 (2020/04/10)
A new reduction of carbamates to N-methyl amines is presented. The magnesium-catalyzed reduction reaction allows the conversion of cyclic and linear carbamates, including N-Boc protected amines, into the corresponding N-methyl amines and amino alcohols which are of significant interest due to their presence in many biologically active molecules. Furthermore, the reduction can be extended to the formation of N-trideuteromethyl labeled amines.
N-Monomethylation of Aromatic Amines with Methanol via PNHP-Pincer Ru Catalysts
Ogata, Osamu,Nara, Hideki,Fujiwhara, Mitsuhiko,Matsumura, Kazuhiko,Kayaki, Yoshihito
supporting information, p. 3866 - 3870 (2018/07/25)
The use of methanol for the selective methylation of aromatic amines with RuHCl(CO)(PNHP) (PNHP = bis(2-diphenylphosphinoethyl)amine) is reported. Various aromatic amines were transformed into their corresponding monomethylated secondary amines in high yields at 150 °C with a very low catalyst loading (0.02-0.1 mol %) in the presence of KOtBu (20-60 mol %). The catalyst precursor, RuHCl(CO)(PNHP), was converted to [RuH(CO)2(PNHP)]+ under the catalytic conditions and also serves as a highly effective catalyst. The robustness of this catalyst contributes to its outstanding catalytic activity, even under reaction conditions, in which CO is liberated from methanol.
N -Monomethylation of amines using paraformaldehyde and H2
Wang, Hongli,Huang, Yongji,Dai, Xingchao,Shi, Feng
supporting information, p. 5542 - 5545 (2017/07/06)
The selective N-monomethylation of amines is an important topic in fine chemical synthesis. Herein, for the first time, we described a selective N-monomethylation reaction of amines with paraformaldehyde and H2 in the presence of a CuAlOx catalyst. A variety of amines, including primary aromatic amines, benzylamine and cyclohexylamine, as well as secondary amines, have been shown to be compatible with this reaction.
Synthetic routes to, transformations of, and rather surprising stabilities of (N-Methyl-N-phenylcarbamoyl)sulfenyl Chloride, ((N-Methyl-N-phenylcarbamoyl) dithio)carbonyl chloride, and related compounds
Schrader, Alex M.,Schroll, Alayne L.,Barany, George
experimental part, p. 7882 - 7892 (2011/12/14)
(Figure presented) The title compound classes, (carbamoyl)sulfenyl chlorides and ((carbamoyl)dithio)carbonyl chlorides, have been implicated previously as unstable, albeit trappable, intermediates in organosulfur chemistry. The presentwork reports for each of these functional groups: (i) several routes to prepare it in the N-methylaniline family; (ii) its direct structural characterization by several spectroscopic techniques; (iii) its rather unexpected stability and its ultimate fatewhen it decomposes; (iv) a series of further chemical transformations that give highly stable derivatives, each in turn subject to thorough characterization. Relevant kinetic and mechanistic experiments were carried out, including some with p-methyl- and 2,6-dimethyl-substituted N-methylanilines. Given that the title compounds can be isolated and are relatively stable, they may find applications in the preparation of thiolyzable and/or photolabile protecting groups for the sulfhydryl function of cysteine and for the development of new protein synthesis and modification reagents
