17508-50-8Relevant academic research and scientific papers
Chiral imine-containing quinoline oxazoline compound and metal complex thereof as well as preparation method and application
-
Paragraph 0143-0149, (2022/01/12)
The invention discloses a chiral imine-containing quinoline oxazoline compound which is high in optical purity and has a structural formula as shown in a formula (1), and discloses a preparation method of the chiral imine-containing quinoline oxazoline compound. The invention also discloses a metal complex obtained by complexing the chiral imine-containing quinoline oxazoline compound and a transition metal salt, wherein the metal complex is shown as a formula (6). The synthetic route is efficient, and the total yield of two steps can reach 85%. The metal complex of the chiral imine-containing quinoline oxazoline compound can be used as a catalyst to catalyze hydrosilylation or hydroboration on a carbon-carbon or carbon heteroatom double bond, and is especially suitable for preparing chiral organic compounds with high regioselectivity and optical selectivity.
Iodine-mediated 1,2-aryl migration of primary benzhydryl amines
Chang, Junbiao,Du, Yangxu,Hao, Wei,Hou, Jiao,Lu, Qing,Yu, Wenquan
supporting information, p. 16223 - 16226 (2021/09/22)
An iodine-mediated 1,2-aryl migration reaction of primary benzhydryl amines under transition metal-free conditions has been achieved. The crude imines generated by this rearrangement reaction can be directly transformed into various aromatic secondary ami
Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines
Kathuria, Lakshay,Samuelson, Ashoka G.
, (2020/12/28)
Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands.
Deposition of highly dispersed gold nanoparticles onto metal phosphates by deposition-precipitation with aqueous ammonia
Kamata, Keigo,Miura, Hiroki,Nishio, Hidenori,Shishido, Tetsuya
, p. 7141 - 7150 (2021/11/17)
An efficient method for depositing gold nanoparticles onto metal phosphate has been developed. Deposition-precipitation with aqueous ammonia enabled small gold nanoparticles to be deposited onto a series of metal phosphates with high dispersity and density. A detailed investigation of the mechanism of the formation of gold nanoparticles corroborated that strong interaction between a gold-ammine complex formed by the treatment of HAuCl4 with ammonia and positively-charged metal phosphates was responsible for the formation of highly dispersed gold nanoparticles. Furthermore, the thus-prepared gold catalysts supported on metal phosphates showed higher catalytic activity than those supported on metal oxides for the hydroamination of terminal alkynes. This journal is
Cu/Ni-doped sulfated zirconium oxide immobilized on CdFe2O4 NPs: a cheap, sustainable and magnetically recyclable inorgano-catalyst for the efficient preparation of α-aminonitriles in aqueous media
Nasseri, Mohammad Ali,Ramezani-Moghadam, Simin,Kazemnejadi, Milad,Allahresani, Ali
, p. 4233 - 4256 (2020/07/08)
Abstract: A new multifunctional bimetallic nanocatalyst was prepared by immobilization of Cu/Ni-doped sulfated zirconium oxide on magnetic cadmium ferrite (CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni) and used as an efficient recyclable catalyst for one-pot as well as stepwise preparation of α-aminonitriles under mild conditions. The magnetic nanocatalyst was characterized by FTIR, TGA, VSM, XRD, EDX, FE-SEM, and TEM analyses. Also, the surface acidity of the catalyst was measured by pyridine adsorption assay. The catalyst possesses various active sites which could catalyst a variety of aromatic and aliphatic aldehydes to the corresponding α-amionitriles under moderate to high yields in the presence of aniline. Furthermore, transformation of ketones to the desired α-amionitriles and some bis-aminonitriles was also performed by this method. The catalyst could be readily recovered from the reaction mixture and reused for several times without significant loss of activity. Graphic abstract: A general and efficient method has been developed for transformation of a variety of aliphatic, aromatic aldehydes and ketones to the corresponding α-aminonitriles using a multifunctional recyclable CdFe2O4@SiO2@ZrO2/SO42?/Cu/Ni nanocatalyst.[Figure not available: see fulltext.]
Synthesis and application of axially chiral biscarbolines with functional N-O and sulfone for 1,2-transfer hydrogenations of ketimines
Xing, Yongfei,Wu, Shijie,Dong, Mengxian,Wang, Jie,Liu, Li,Zhu, Huajie
supporting information, (2019/08/08)
A series of axially chiral biscarboline-based sulfones were synthesized from L-tryptophane and applied for enantioselective 1,2-transfer hydrogenations of ketimines using trichlorosilane. The catalyst 4e, which had a tertiary butyl group, exhibited a good conversion and high enantioselectivities up to 96%ee in the series of reactions.
P-Stereogenic and Non-P-Stereogenic Ir-MaxPHOX in the Asymmetric Hydrogenation of N -Aryl Imines. Isolation and X-ray Analysis of Imine Iridacycles
Salomó, Ernest,Rojo, Pep,Hernández-Lladó, Pol,Riera, Antoni,Verdaguer, Xavier
, p. 4618 - 4627 (2018/04/26)
A small library of Ir-MaxPHOX catalysts has been applied to the asymmetric hydrogenation of N-aryl imines. A structure-activity analysis of the three-chiral-center MaxPHOX ligand has been performed. Using complex 1b, the hydrogenation of N-aryl imines too
Transition-Metal-Free Addition of Acetylenes to Ketimines: the First Base-Catalyzed Ethynylation of the C=N Bond
Bidusenko, Ivan A.,Schmidt, Elena Yu.,Ushakov, Igor A.,Trofimov, Boris A.
supporting information, p. 4845 - 4849 (2018/09/14)
A one-pot transition metal-free synthesis of propargylamines in good to excellent yield from ketone-derived imines and aryl- and hetarylacetylenes in the presence of KOBut/DMSO superbase system (40 °C, 10 min) has been developed. The reaction i
Palladium-catalyzed aerobic oxidative hydroamination of vinylarenes using anilines: A wacker-type amination pathway
Song, Eunsun,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 5264 - 5267 (2017/11/06)
A palladium-catalyzed intermolecular hydroamination of vinylarene derivatives using anilines has been developed for the first time under aerobic conditions, where the regioselective formation of N-arylketimines is accomplished. The current aerobic oxidative hydroamination pathway of anilines is distinct from that of palladiumcatalyzed hydroamination reactions that proceed to give sec-arylethylamine and arylethylamine derivatives, identifying a longstanding missing reaction pathway, Wacker-type amination, to N-arylketimines using anilines. The ready availability of both starting materials, vinylarenes and anilines, offers an attractive and facile synthetic route to N-arylketimines in good to excellent yields.
“Half-sandwich” Schiff-base Ir(III) complexes as anticancer agents
Mou, Ze-dong,Deng, Ning,Zhang, Feng,Zhang, Jiaying,Cen, Juan,Zhang, Xia
, p. 72 - 82 (2017/06/27)
A series of “half-sandwich” Schiff-base Ir(III) complexes were synthesized and investigated for their in vitro activities against the leukemia K562 cell line. These compounds demonstrated antiproliferative activities against K562 cells with IC50 values of 0.26–4.77 μM. In particular, compound 10c showed cytotoxicity against five cancer cell lines/sublines and stronger activities than cisplatin in K562, K562/A02, MCF-7, MCF-7/ADM, and A549 cells. Mechanism studies illustrated that compound 10c increased the level of reactive oxygen species and induced apoptosis of K562 cells. This compound effectively decreased the mitochondrial membrane potential and the protein level of Bcl-2. It also increased the protein levels of Bax, caspase-3, and caspase-9, and led to release of cytochrome c in K562 cells, indicating that the apoptosis induced by compound 10c was mediated by the intrinsic mitochondria apoptosis pathway.
