770-03-6Relevant academic research and scientific papers
Method for realizing N-alkylation by using alcohols as carbon source under photocatalysis
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Paragraph 0048-0057, (2021/03/13)
The invention discloses a method for realizing N-alkylation by using alcohols as a carbon source under photocatalysis, and belongs to the technical field of catalytic synthesis. Alcohol, a substrate raw material and a catalyst are placed in a reaction device, ultraviolet and/or visible light irradiation is carried out in an inert atmosphere, after the irradiation is finished, solid-liquid separation is carried out to remove the catalyst, and an N-alkylation product can be obtained through extraction, distillation and purification, wherein the substrate raw material comprises any one of an amine compound, an aromatic nitro compound or an aromatic nitrile compound, the alcohol comprises any one or more of soluble primary alcohols, and the catalyst is metal oxide/titanium dioxide or metal sulfide/titanium dioxide. The method is simple and easy to operate, can be used for efficient photocatalysis one-pot multi-step hydrogenation N-alkylation reaction, and is mild in reaction condition, high in chemical selectivity of N-alkylamine, good in catalyst stability and easy to recycle.
Visible-Light-Enabled Direct Decarboxylative N-Alkylation
Arman, Hadi D.,Dang, Hang T.,Haug, Graham C.,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Vuong, Ngan T. H.
supporting information, p. 7921 - 7927 (2020/04/10)
The development of efficient and selective C?N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.
A general method for N-methylation of amines and nitro compounds with dimethylsulfoxide
Jiang, Xue,Wang, Chao,Wei, Yawen,Xue, Dong,Liu, Zhaotie,Xiao, Jianliang
supporting information, p. 58 - 63 (2014/01/17)
DMSO methylates a broad range of amines in the presence of formic acid, providing a novel, green and practical method for amine methylation. The protocol also allows the one-pot transformation of aromatic nitro compounds into dimethylated amines in the presence of a simple iron catalyst. Not just a solvent: DMSO methylates a broad range of amines in the presence of formic acid, providing a novel, green and practical method for amine methylation. The protocol also allows the one-pot transformation of aromatic nitro compounds into dimethylated amines in the presence of a simple iron catalyst. Copyright
Iron(III)-catalyzed C-H functionalization: Ortho-benzoyloxylation of N,N-dialkylanilines and its application to 1,4-benzoxazepines
Chiranjeevi, Barreddi,Vinayak, Botla,Parsharamulu, Thupakula,PhaniBabu, Vemulapalli S.,Jagadeesh, Bharatam,Sridhar, Balasubramanian,Chandrasekharam, Malapaka
, p. 7839 - 7849 (2015/01/16)
A C-O bond-formation reaction that proceeds through C-H functionalization of N,N-dialkylanilines at the ortho-position is presented. The iron-catalyzed selective ortho-benzoyloxylation follows a polar Friedel-Crafts-like mechanism and is sensitive to the nucleophilicity of the anilines. The benzoyl-oxylation of a variety of N,N-disubstituted anilines and Nphenyl heterocycles is carried out under extremely mild conditions. Furthermore, the methodology has been successfully employed for the generation of 1,4-benzoxazepines and oaminophenols.
Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluation
Chiranjeevi, Barreddi,Koyyada, Ganesh,Prabusreenivasan,Kumar, Vanaja,Sujitha, Pombala,Kumar, C. Ganesh,Sridhar,Shaik, Saida,Chandrasekharam, Malapaka
, p. 16475 - 16485 (2013/09/23)
Naturally occurring dibenzofuran motifs represent promising lead structures for the development of novel antimycobacterial agents. Prompted by our recent development of cross dehydrogenative coupling using iron catalysis, we extended our strategy to synthesize 14 novel anilinodibenzofuranols and they were explored for anti-tubercular and cytotoxic activities. Consistent with our hypothesis, DBF-3, 14 and 16 exhibited promising activity against two strains (M. tuberculosis H37Rv and the clinical S, H, R, and E resistant isolate), while DBF-13, 18 exhibited selective inhibitory activity only against the clinical S, H, R and E resistant isolate. However, the compounds DBF-4 and DBF-8 showed promising and selective antitumor activity against the tested cancer cell lines. The Royal Society of Chemistry 2013.
Cerium-containing MCM-41 catalyst for selective oxidative arene cross-dehydrogenative coupling reactions
Akondi, Adinarayana Murthy,Trivedi, Rajiv,Sreedhar, Bojja,Kantam, Mannepalli Lakshmi,Bhargava, Suresh
, p. 35 - 44 (2013/01/15)
Cerium (IV)-mediated intermolecular direct biaryl coupling of aromatic tertiary amines and naphthol via dual CH bond activation has been reported. The new CC bond is formed regioselectively ortho to the amino and hydroxyl substituents under oxidative conditions to give substituted bifunctional amino naphthols. We report here the use of Ce-MCM-41 catalyst for the synthesis of these unsymmetrical biaryls via oxidative cross coupling under mild conditions. The catalyst was recovered by simple filtration and reused for several cycles with consistent activity.
Iron-catalyzed regioselective direct oxidative aryl-aryl cross-coupling
Chandrasekharam, Malapaka,Chiranjeevi, Barreddi,Gupta, Kankatala S.V.,Sridhar
experimental part, p. 10229 - 10235 (2012/01/15)
Regioselective iron-catalyzed cross-dehydrogenative coupling (CDC) of two aromatic compounds using tert-BuOOH as oxidant under mild conditions has been reported. The direct oxidative coupling reaction is selective toward creation of a carbon-carbon bond at the position ortho to the functional groups of the substrates, completely preventing the homocoupled products. The C-C bond-forming reaction makes the method versatile, leading to functionalized 2,2′-disubstituted biaryls (Figure presented).
Carbamate synthesis from amines and dialkyl carbonate over inexpensive and clean acidic catalyst-Sulfamic acid
Wang, Bo,He, Jing,Sun, Run Cang
scheme or table, p. 794 - 797 (2011/11/13)
Sulfamic acid has been proved to be the most efficient and recyclable catalyst in carbamate synthesis from alkylamine and dialkyl carbonate. High selectivity, cost-efficiency and simple product separation were the advantageous features obtained in this process. Sulfamic acid could be reused several times and keep its initial activity in the recycle runs. In addition, sulfamic acid has also exhibited the potential catalytic ability for alkylation of aromatic amines.
