13533-22-7Relevant academic research and scientific papers
Rational Design of Cobalt-Platinum Alloy Decorated Cobalt Nanoparticles for One-Pot Synthesis of Imines from Nitroarenes and Aldehydes
Gong, Wanbing,Han, Miaomiao,Chen, Chun,Lin, Yue,Wang, Guozhong,Zhang, Haimin,Zhao, Huijun
, p. 5948 - 5958 (2020/10/02)
Developing high-performance heterogeneous catalysts for one-pot reductive amination reactions is critically important for pharmaceutical and agrochemical synthetic industries. In this work, N-doped carbon nanotubes supported CoPt alloy decorated Co nanoparticles (NPs) are successfully fabricated. As a consequence, the resultant catalyst exhibits desirable activity, selectivity and stability toward the one-pot synthesis of imines. More importantly, the extensive experimental studies and density function theory (DFT) calculations results reveal that the high catalytic activity of the catalyst is mainly due to the co-existence of CoPt alloy NPs and Co NPs with Co?Nx active sites. The high selectivity of imines could be ascribed to the following aspects: (1) competitively preferred adsorption of nitroarenes to avoid side-hydrogenation of aldehydes; (2) weakened adsorption of imines to minimize its over-hydrogenation. This work may provide a promising direction and strategy to design high-performance reductive amination catalysts for industrial applications.
One-pot solvothermal synthesized CoS2@MoS2 nanocomposites for selective reduction coupling reaction to synthesize imines
Han, Wenpeng,Wang, Junwei,Li, Xuekuan,Zhou, Ligong,Yang, Ying,Tang, Mingxing,Ge, Hui
, p. 86 - 91 (2019/03/14)
Selective reduction coupling of nitroaromatics and aldehydes for imines synthesis has been investigated by using a series of bifunctional CoS2@MoS2 catalysts prepared by one-pot solvothermal method. Under optimal Co/Mo ratio of 0.75 and preparation temperature (180 °C), CoS2@MoS2–180-0.75 catalyst shows 96.5% nitrobenzene conversion, 93.0% imine selectivity and good versatility for substituted nitrobenzene and different aldehydes under mild conditions (60 °C, 1.5 MPa H2). The characterizations reveal that high nitroaromatics hydrogenation activity and good selectivity are mainly due to the formation of CoMoS phase, the coupling reaction between aniline derivatives and aldehydes is achieved by the appropriate acidity of CoS2@MoS2 nanocomposites.
Heterogeneous Catalysis with Basic Compounds to Achieve the Synthesis and C-N Cleavage of Azetidin-2-ones under Microwave Irradiation
Alcaraz, Yolanda,Cruz, Francisco,De La Cruz, Fabiola N.,Delgado, Francisco,Domínguez, José Manuel,Galván, Adriana,Gomez, Clarisa Villegas,Martínez, Merced,Vázquez, Miguel A.
supporting information, p. 3625 - 3637 (2019/09/30)
The synthesis of azetidin-2-ones with a completely heterogeneous catalysis is reported. The use of basic compounds as solid catalysts allowed for the synthesis of azetidin-2-ones under microwave irradiation without organic additives such as triethylamine. An excellent catalyst for this transformation was Mg-Al hydroxide (MAH). The present methodology offers the advantages of non-hazardous reaction conditions, short reaction times, high yields, and catalyst reusability. Different substitution groups were tested on the imines and acyl chlorides to explore the scope of the reaction. Unconventional N-C4 bond cleavage was detected in azetidin-2-ones. MAH was characterized by N 2 adsorption-desorption, X-ray diffraction (XRD), scanning electron microscopy (SEM), and high-resolution transmission electron microscopy (HR-TEM).
Flash vacuum pyrolysis of azolylacroleins and azolylbutadienes
Lucero, Paola L.,Peláez, Walter J.,Riedl, Zsuzsanna,Hajós, Gy?rgy,Moyano, Elizabeth L.,Yranzo, Gloria I.
supporting information; experimental part, p. 1299 - 1305 (2012/02/13)
2-Aryl-5-acroleinyl-1,2,3,4-tetrazoles (1a-d) and 2-aryl-5-butadienyl-1,2, 3,4-tetrazoles (1e-g) were subjected to flash vacuum pyrolysis. Acroleinyl derivatives resulted in nitrogen extrusion to give nitrilimines followed by ring closure to give the corresponding indazoles 3a-d in good yields. On the other hand, butadiene derivatives underwent ring fragmentation to give p-substituted anilines without formation of the expected indazoles. Differences between thermal behaviour of 2-(4-chlorophenyl)-5-acroleinyl-1,2,3,4-tetrazole (1c) and 1-(4-chlorophenyl)-4-acroleinyl-1,2,3-triazole (2) were studied in details. DFT calculations have been used to examine the nitrilimine and carbene nature of the intermediates involved in the thermal reactions of azolyl derivatives.
Solvent-free addition reaction of allylzinc bromide and aldimines
Zhang, Yumei,Han, Minghu,Yan, Tingli
body text, p. 2689 - 2693 (2012/07/14)
(Chemical Equation Presented) Barbier-type allylation of aldimines with allylzinc bromide took place rapidly under solvent-free conditions. The procedure is environmentally benign and operationally simple, has good regioselectivity, and gives good to exce
Solvent-free allylation and benzylation of aldimines mediated by zinc powder
Zhang, Yumei,Yan, Tingli,Cheng, Wei,Zuo, Jianming,Zhao, Weijie
body text, p. 2925 - 2928 (2009/07/19)
A rapid and efficient procedure for allylation and benzylation of aldimines mediated by zinc powder under solvent-free conditions is described. The procedure is operationally simple, higher regioselective, and gives good to excellent yields.
Antifungal and cytotoxic activities of some N-substituted aniline derivatives bearing a hetaryl fragment
Kouznetsov, Vladímir V.,Vargas Méndez, Leonor Y.,Sortino, Maximiliano,Vásquez, Yelkaira,Gupta, Mahabir P.,Freile, Mónica,Enriz, Ricardo D.,Zacchino, Susana A.
, p. 794 - 809 (2008/09/17)
Diverse N-substituted anilines bearing hetaryl fragments were easily prepared from corresponding aldimines derived from commercially available aromatic aldehydes and anilines. 2-Furyl substituted anilines showed very good antifungal activities against dermatophytes, particularly against Trichophyton rubrum (MIC = 3.12-6.25 μg/mL). In addition, all active compounds, 45-47, 73, and 74, were tested for cytotoxic activities against breast (MCF-7), lung (H-460), and central nervous system (SF-268) human cancer cell lines with the NCI-anticancer-drug screen. The activity of amines described in this paper, along with the low toxicity of most of them, shows promise for the future development of non-toxic new antimycotic agents.
In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels-Alder reactions
Melendez Gomez, Carlos M.,Kouznetsov, Vladimir V.,Sortino, Maximiliano A.,Alvarez, Sandra L.,Zacchino, Susana A.
body text, p. 7908 - 7920 (2009/04/11)
Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels-Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds.
An efficient synthesis of isoindolo[2,1-a]quinoline derivatives via imino Diels-Alder and intramolecular Diels-Alder reactions with furan
Kouznetsov, Vladimir V.,Cruz, Uriel Mora,Zubkov, Fedor I.,Nikitina, Eugenia V.
, p. 375 - 384 (2008/01/06)
The straightforward synthesis of new isoindolo[2,1-a]quinoline derivatives from 2,4-disubstituted 1,2,3,4-tetrahydroquinolines bearing a furan fragment via the intramolecular Diels-Alder reaction is reported. The synthesis of key precursors was realized w
Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc
Kojima, Keisuke,Kimura, Masanari,Ueda, Satoshi,Tamaru, Yoshinao
, p. 7512 - 7520 (2007/10/03)
Ni(acac)2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous (E)-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes (1) in excellent yields. Aliphatic aldehydes react similarly and give (E)-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes (1) in slightly reduced yields. When the alkyl groups are bulky, in addition to 1 are formed (E)-1-arylamino-1-alkyl-4-methyl-5-phenyl-3-pentenes (1′) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish (E)-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols (4) and (E)-5-arylamino-7-methyl-9- phenyl-7-nonen-1-ols (5), respectively, in good yields with excellent E-stereoselectivity.
