20172-42-3Relevant academic research and scientific papers
Asymmetric synthesis of (α-amino)phosphonic acid amphiphiles using chiral P-H spirophosphoranes
Dejugnat, Christophe,Etemad-Moghadam, Guita,Rico-Lattes, Isabelle
, p. 1858 - 1859 (2003)
Chiral P-H spirophosphoranes reacted with long-chain prochiral aldimines and, after selective hydrolysis, afforded (α-amino)phosphonic acid amphiphiles in both enantiopure forms.
Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation
Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek
, p. 6705 - 6716 (2021/12/31)
We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.
Molybdenum Nitride Nanocatalyst Derived from Melamine and Polyoxometalate-based Hybrid for Oxidative Coupling of Amines to Imines with Air
Li, Yue,Xiao, Kang,Li, Jingjing,Jiang, Pingping,Jiang, Yuchen,Du, Shengyu,Leng, Yan
, p. 4317 - 4323 (2018/09/06)
Molybdenum nitride (Mo2N) is one of the most promising alternative catalysts for a wide range of Pt-catalyzed catalytic applications but is seldom investigated in oxidative coupling of amines to imines. A Mo2N-based nanocatalyst is successfully achieved by the hybridization of PMo12O403? (PMo)-paired ionic pyridine-4-carboxylic acid (PC) and melamine (Mel), followed by calcination in N2. Melamine acts as an outstanding carburization and nitridation reagent that can convert into carbon nitride, and meanwhile the released N element react with Mo species in PMo to form Mo2N. The obtained catalyst PC-PMo-Mel-800 exhibits high activity and remarkable stability for the oxidative coupling of amines to imines under solvent-free and atmospheric conditions. This is the first case of Mo2N-catalyzed oxidative coupling reaction catalyst. The strategy reported herein for fabricating Mo2N may provide a significant and interesting approach to design more transition metal nitrides for wide catalytic applications.
Manganese catalyzed reductive amination of aldehydes using hydrogen as a reductant
Wei, Duo,Bruneau-Voisine, Antoine,Valyaev, Dmitry A.,Lugan, No?l,Sortais, Jean-Baptiste
supporting information, p. 4302 - 4305 (2018/05/03)
A one-pot two-step procedure was developed for the alkylation of amines via reductive amination of aldehydes using molecular dihydrogen as a reductant in the presence of a manganese pyridinyl-phosphine complex as a pre-catalyst. After the initial condensation step, the reduction of imines formed in situ is performed under mild conditions (50-100 °C) with 2 mol% of catalyst and 5 mol% of tBuOK under 50 bar of hydrogen. Excellent yields (>90%) were obtained for a large combination of aldehydes and amines (40 examples), including aliphatic aldehydes and amino-alcohols.
Ligand-Controlled Inversion of Diastereo- and Enantioselectivity in Silver-Catalyzed Azomethine Ylide-Imine Cycloaddition of Glycine Aldimino Esters with Imines
Yu, Bo,Yang, Ke-Fang,Bai, Xing-Feng,Cao, Jian,Zheng, Zhan-Jiang,Cui, Yu-Ming,Xu, Zheng,Li, Li,Xu, Li-Wen
supporting information, p. 2551 - 2554 (2018/05/17)
A highly diastereo- and enantioselective silver-catalyzed azomethine ylide-imine (AYI) cycloaddition reaction of glycine aldimino esters with imines was developed in which the Xing-Phos-controlled syn-selective or DTBM-Segphos-induced anti-selective AYI cycloaddition reaction could be applied to the synthesis of a variety of stereodivergent 1-alkyl-2,5-substituted imidazolidines with high yields and excellent enantioselectivities (up to 99% ee) as well as good diastereoselectivities (up to 99:1 dr) under mild reaction conditions.
Osmium Hydride Acetylacetonate Complexes and Their Application in Acceptorless Dehydrogenative Coupling of Alcohols and Amines and for the Dehydrogenation of Cyclic Amines
Esteruelas, Miguel A.,Lezáun, Virginia,Martínez, Antonio,Oliván, Montserrat,Onate, Enrique
, p. 2996 - 3004 (2017/08/21)
The preparation of new osmium hydride complexes, starting from OsH6(PiPr3)2 (1) and OsH2Cl2(PiPr3)2 (2), and their catalytic activity in acceptorless dehydrogenative coupling of alcohols and amines and in dehydrogenation of cyclic amines are reported. Complex 1 reacts with acetylacetone (Hacac) to give the classical trihydride OsH3(acac)(PiPr3)2 (3). The protonation of 3 with triflic acid (HOTf) produces the release of H2 and the formation of the unsaturated osmium(IV) dihydride [OsH2(acac)(PiPr3)2]OTf (4), which is also prepared by starting from 2 via the intermediate OsH2Cl(acac)(PiPr3)2 (5). Treatment of an acetylacetone solution of 5 with KOH affords Os(acac)2(PiPr3)2 (6). In the presence of 5 mol % of KOH, complexes 3-6 promote the coupling of benzyl alcohol and aniline to give N-benzylideneaniline and H2. Under the same conditions, complex 3 catalyzes a wide range of analogous couplings to afford a variety of imines, including aliphatic imines, with yields between 90 and 40% after 1-48 h. Complex 3 also catalyzes the dehydrogenation of cyclic amines. According to the amount of H2 released by each 1 g of employed substrate, the amines have been classified into three classes: poor (1,2,3,4-tetrahydroquinaldine, 2-methylindoline, and 2,6-dimethylpiperidine), moderate (1,2,3,4-tetrahydroquinoline and 6-methyl-1,2,3,4-tetrahydroquinoline), and good hydrogen donors (1,2,3,4-tetrahydroisoquinoline).
Aryl-alkyl-lysines: Membrane-Active Fungicides That Act against Biofilms of Candida albicans
Ghosh, Chandradhish,Yadav, Vikas,Younis, Waleed,Mohammad, Haroon,Hegazy, Youssef A.,Seleem, Mohamed N.,Sanyal, Kaustuv,Haldar, Jayanta
, p. 293 - 301 (2017/04/21)
Mortality due to pathogenic fungi has been exacerbated by the rapid development of resistance to frontline antifungal drugs. Fungicidal compounds with novel mechanisms of action are urgently needed. Aryl-alkyl-lysines, which are membrane-active small molecules, were earlier shown to be broad-spectrum antibacterial agents with potency in vitro and in vivo. Herein, we report the antifungal properties of aryl-alkyl-lysines. After identifying the most active compound (NCK-10), we tested its activity against a panel of clinically relevant pathogenic fungi and examined NCK-10's effect against immature and mature biofilms of Candida albicans. NCK-10 was capable of inhibiting the growth of various species of fungi (including Candida spp., Cryptococcus spp., and Aspergillus fumigatus) at concentrations similar to those of antifungal drugs used clinically. It was observed that polarization and permeability of the fungal cell membrane were compromised upon addition of NCK-10, indicating its mechanism is disruption of the fungal cell membrane. In addition to interfering with the growth of planktonic fungi, NCK-10 demonstrated the ability to both inhibit biofilm formation and reduce the metabolic activity of cells in C. albicans biofilm. Additionally, our compound was capable of crossing the blood-brain barrier in an in vitro model, expanding the potential antifungal applications for NCK-10. Overall, aryl-alkyl-lysines were found to be excellent compounds that warrant further investigation as novel antifungal agents.
Small molecular antibacterial peptoid mimics: The simpler the better!
Ghosh, Chandradhish,Manjunath, Goutham B.,Akkapeddi, Padma,Yarlagadda, Venkateswarlu,Hoque, Jiaul,Uppu, Divakara S.S.M.,Konai, Mohini M.,Haldar, Jayanta
, p. 1428 - 1436 (2014/03/21)
The emergence of multidrug resistant bacteria compounded by the depleting arsenal of antibiotics has accelerated efforts toward development of antibiotics with novel mechanisms of action. In this report, we present a series of small molecular antibacterial peptoid mimics which exhibit high in vitro potency against a variety of Gram-positive and Gram-negative bacteria, including drug-resistant species such as methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecium. The highlight of these compounds is their superior activity against the major nosocomial pathogen Pseudomonas aeruginosa. Nontoxic toward mammalian cells, these rapidly bactericidal compounds primarily act by permeabilization and depolarization of bacterial membrane. Synthetically simple and selectively antibacterial, these compounds can be developed into a newer class of therapeutic agents against multidrug resistant bacterial species.
Copper-catalyzed highly efficient aerobic oxidative synthesis of imines from alcohols and amines
Kang, Qiang,Zhang, Yugen
experimental part, p. 1016 - 1019 (2012/06/04)
A highly efficient and green tandem imine synthesis from alcohol and amine with molecular oxygen as oxidant was achieved by using a remarkable low catalyst-loading, with a commercially available and environmentally benign copper catalyst.
Highly active and selective synthesis of imines from alcohols and amines or nitroarenes catalyzed by Pd/DNA in water with dehydrogenation
Tang, Lin,Sun, Huayin,Li, Yunfeng,Zha, Zhenggen,Wang, Zhiyong
, p. 3423 - 3428 (2013/01/16)
A direct imination was developed from alcohols and amines under catalysis of Pd/DNA by dehydrogenation without additional oxidant, affording the corresponding imines in moderate to good yields with excellent chemoselectivity. By virtue of the liberated molecular hydrogen, the nitroarenes could also be deoxidized in situ into amines and a one-pot tandem synthesis of imines was achieved from nitroarenes. This heterogeneous catalyst can be recovered and reused at least five times by taking advantage of its water-soluble reversibility. All these conformations were performed smoothly in water under mild conditions, and an atom economical and environmentally benign synthesis was embodied in this imination.
