872-32-2Relevant articles and documents
Intramolecular cyclization of aminoalkynes catalyzed by PdMo 3S4 cubane clusters
Takei, Izuru,Enta, Yutaka,Wakebe, Youhei,Suzuki, Toshiaki,Hidai, Masanobu
, p. 590 - 591 (2006)
PdMo3S4 cubane clusters [(Cp*Mo) 3(μ3-S)4Pd(L)][PF6] (Cp* = η5-C5Me5; L = dba (2), ma (3); dba = dibenzylideneacetone, ma = maleic anhydride) showed high catalytic activity for the intramolecular hydroamination of aminoalkynes to afford the corresponding cyclic imines in good yields under mild conditions. A molecular structure of 3 has been determined by X-ray diffraction study. Copyright
Gold(I) complexes with "normal" 1,2,3-triazolylidene ligands: Synthesis and catalytic properties
Schaper, Lars-Arne,Wei, Xuhui,Hock, Sebastian J.,Poethig, Alexander,Oefele, Karl,Cokoja, Mirza,Herrmann, Wolfgang A.,Kuehn, Fritz E.
, p. 3376 - 3384 (2013)
1,2,3-Triazolylidenes as versatile, strong donor ligands have currently experienced a boost in complex synthesis as well as catalytic applications. Although many examples of "abnormal" 1,2,3-triazolylidenes have been described, their "normal" congeners have been barely examined to date (for abnormal carbenes the resonance structures of the carbenes cannot be drawn without adding additional charges, but this is possible for normal carbenes). Furthermore, no instance of utilization of this new ligand class in homogeneous catalysis can be found. Therefore, this work presents a variety of potential precatalysts descending from "normal" 1,2,3-triazolylidene Au chloride complexes. Synthesis and thorough characterization of the new compounds are presented, together with special ligand features such as buried volume and suspected anagostic interactions. The activity of the isolated precatalysts is examined in the intramolecular hydroamination of alkynes and compared with that of a popular imidazolylidene system. It is found that the activity of the best-performing "normal" 1,2,3-triazolylidene systems is quite similar to that of the imidazolylidene systems. However, mercury drop poisoning experiments suggest that improvements in ligand design are required to enhance catalyst stability.
Inhibitors of polyamine biosynthesis. 3. (±) 5 amino 2 hydrazino 2 methylpentanoic acid, an inhibitor of ornithine decarboxylase
Abdel Monem,Newton,Weeks
, p. 945 - 948 (1975)
(±) 5 Amino 2 hydrazino 2 methylpentanoic acid [α hydrazino α methyl (±) ornithine] was obtained from 1 phthalimidopentan 4 one by treatment with hydrazine and KCN followed by acid hydrolysis. The title compound was found in vitro to be a potent competitive inhibitor of ornithine decarboxylase obtained from the prostate glands of rats. This inhibition was abolished at high concentrations of pyridoxal phosphate. The title compound also blocked the increase in putrescine levels normally observed in bovine lymphocytes transformed by conconavalin A.
Mononuclear rhodium(I) complexes with chelating N-heterocyclic carbene ligands - Catalytic activity for intramolecular hydroamination
Burling, Suzanne,Field, Leslie D.,Li, Hsiu L.,Messerle, Barbara A.,Turner, Peter
, p. 3179 - 3184 (2003)
The mononuclear cationic RhI complexes [Rh(cod)(mdd)] +X- and [Rh(CO)2(mdd)]+X - (X = BPh4, PF6) containing the chelating bidentate N-heterocyclic carbene ligand 1,1′-methylene - 3,3′-dimethyldiimidazoline-2,2′-diylidene (mdd) have been synthesised and spectroscopically characterised. The complexes [Rh(cod)(mdd)]+BPh4- and [Rh(CO) 2(mdd)]+PF6- have also been characterised by X-ray crystallography. The dicarbonyl complexes catalyse the intramolecular hydroamination of 4-pentyn-1-amine to 2-methyl-1-pyrroline. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
Dendrimeric and Corresponding Monometallic Iridium(III) Catalysts Bound to Carbon Nanotubes Used in Hydroamination Transformations
Pernik, Indrek,Desmecht, Antonin,Messerle, Barbara A.,Hermans, Sophie,Riant, Olivier
supporting information, p. 3448 - 3457 (2021/08/30)
This report describes the synthesis of a carbon nanotube-bound dendrimer and three carbon nanotube-bound monometallic complexes and their use as catalysts. The polyamidoamine third generation dendrimer used here incorporates pyrazole-triazole moieties suitable for ligating iridium(III) centres. The monometallic complexes use the same pyrazole-triazole ligands coordinated to an iridium(III) centre. All catalysts were characterized using ICP-AES and XPS to evaluate their metal loadings on the carbon surface with significantly higher relative weight percentage of iridium determined for the denrimeric species. The catalytic activity and practicality of the formed catalysts were tested using two different intramolecular hydroamination reactions.
3-AZABICYCLO(3.1.0)HEXANE DERIVATIVES HAVING KDM5 INHIBITORY ACTIVITY AND USE THEREOF
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Paragraph 0632, (2021/11/13)
The present invention provides KDM5 inhibitor. The compound disclosed herein represented by the general formula (I) : wherein all symbols have the same meanings as the definitions described in the specification; or a salt thereof is useful as a prophylact
Synthesis method of 2-methyl pyrroline
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Paragraph 0014; 0016; 0018, (2020/06/16)
The invention discloses a synthesis method of 2-methyl pyrroline. The preparation method comprises the following steps: adding valeryl chloride and phthaloyl potassium salt into a high-boiling-point solvent and carrying out heating reflux for 5 to 15 hours; and S2, after the reaction liquid is cooled, filtering the reaction liquid, concentrating the reaction liquid, adding methanol for pulping toobtain a crude product, adding the crude product obtained in S1 into hydrochloric acid for heating reflux, after the reaction is completed, performing concentrating to dryness, adding water into residual liquid for dissolving, adjusting the pH value to be about 11 by using sodium carbonate, performing extracting for 3-5 times by using dichloromethane, and performing concentrating and drying, and distilling to obtain a product. According to the synthetic method of the 2-methyl pyrroline, disclosed by the invention, the used initial raw materials are easy to obtain, the preparation is convenient, the enlarged production is easy, the intermediate product is stable, and the collection efficiency is high.
Simple and reactive Ir(i) N-heterocyclic carbene complexes for alkyne activation
Gatus, Mark R. D.,Pernik, Indrek,Tompsett, Joshua A.,Binding, Samantha C.,Peterson, Matthew B.,Messerle, Barbara A.
supporting information, p. 4333 - 4340 (2019/04/01)
Two simple unsymmetrical monometallic Ir(i) complexes with an N-heterocyclic carbene ligand and an analogous bimetallic Ir(i) complex were synthesised. These complexes were found to be extremely active catalysts for a range of C-X (X = N or O) and Si-N bond forming reactions involving alkyne and imine activation for dihydroalkoxylation, hydroamination and hydrosilylation reactions. These catalysts exhibited reaction rates far exceeding those of other Rh(i) and Ir(i) complexes previously reported. In addition, a small change to the ligand design (phenyl vs. mesityl) substantially affected both the reactivity and product selectivity of the catalyst. The Ir(i) complex bearing a mesitylene wingtip provided unprecedented regioselectivity in the dihydroalkoxylation reaction and a new kinetic product from the typical hydrosilylation protocol of 2-benyzlpyrroline to produce an N-silylaminoalkene. Our mechanistic studies indicated that this transformation proceeded via a dehydrogenative coupling mechanism.
A Commercially Available and User-Friendly Catalyst for Hydroamination Reactions under Technical Conditions
Zelenay, Benjamin,Munton, Peter,Tian, Xiaojie,Díez-González, Silvia
, p. 4725 - 4730 (2019/08/01)
The activity of a simple, commercially available copper salt, [Cu(NCMe)4](BF4) in intramolecular hydroamination reactions of alkynes and allenes is presented. Reactions were successfully carried out in technical acetonitrile in the presence of air. While attempts of alkene hydroamination failed, this catalyst was also found active in intermolecular aza-Michael reactions.
Enhancements in catalytic reactivity and selectivity of homobimetallic complexes containing heteroditopic ligands
Gatus, Mark R. D.,McBurney, Roy T.,Bhadbhade, Mohan,Messerle, Barbara A.
, p. 7457 - 7466 (2017/07/10)
Rh(i) and Ir(i) homobimetallic complexes were synthesised using a heteroditopic ligand system on a xanthene scaffold containing a monodentate N-heterocyclic carbene ligand and a bidentate bis(pyrazol-1-yl)methane ligand. The complexes were tested as catalysts for the two-step dihydroalkoxylation and two-step hydroamination/hydrosilylation reactions. This is the first known report of an organometallic group 9 complex, Ir(i) bimetallic complex, 13, to selectively favour the opposite spirocyclisation product from that reported in the literature, 14cvs.14b. The Ir(i) homobimetallic complex catalyses the intramolecular hydroamination reaction of alkynamines efficiently and proved to be a highly active catalyst for promoting the subsequent hydrosilylation of the pyrrolines; completing the hydrosilylation reactions in less than 40 seconds. A chloro-bridged bimetallic species was observed in the solid state, revealing that the COD co-ligands present underwent an oxidation.
