10468-40-3Relevant academic research and scientific papers
Synthesis of Lepadiformine Using a Hydroamination Transform
Tabor, M. Greg,Shenvi, Ryan A.
, p. 5776 - 5779 (2015)
Dissection of lepadiformine by a double hydroamination transform affords a simple achiral amino diene. This reaction is accomplished in the forward sense by amine-directed hydroboration and an oxidative alkyl shift to nitrogen, both of which occur with hi
New synthesis, properties, and oxidizing ability of 1,3-dimethyl-5,10- methanocycloundeca[4,5]furo[2,3-d]pyrimidin-2,4(1,3H)-dionylium tetrafluoroborate
Naya, Shin-Ichi,Warita, Masato,Mitsumoto, Yuhki,Nitta, Makoto
, p. 9184 - 9190 (2004)
A novel synthesis of 1,3-dimethyl-5,10-methanocycloundeca[4,5]furo[2,3-d] pyrimidin-2,4(1,3H)-dionylium tetrafluoroborate (10+·BF 4-) was accomplished by the reaction of 3,8-methano[11]-annulenone with dimethylbarbituric acid and following acidic cyclization, albeit in low yield. Remarkable structural characteristics were suggested on inspection of the spectral data and MO calculation, and it was clarified that the positive charge is largely localized at the C11. The pK R+ value of cation 10+ was determined spectrophotometrically to be 4.6, which is much smaller by 4.1 pH unit than that of 1,3-dimethyl-7,12-methanocycloundeca[4,5]furo[2,3-d]pyrimidin-2,4(1,3H)- dionylium tetrafluoroborate (pKR+ = 8.7). This value is also smaller by 1.6 pH unit than that of the parent 1,6-methano[11]annulenylium ion (pK R+ = 6.2). The feature is rationalized on the basis of the perturbation derived from the bond fixation of the parent cation. The electrochemical reduction of 10+ exhibited less negative reduction potential at -0.39 (V vs Ag/AgNO3) upon cyclic voltammetry (CV). In a search for reactivity, reactions of 10+ with some nucleophiles, hydride and diethylamine, were carried out to give mixtures of C11- and C13-adducts. In both reactions, the methano-bridge controls the nucleophilic attacks to the C13 to favor exo selectivity. The photoinduced autorecycling oxidation reactions of 10+·BF4- toward some amines under aerobic conditions were carried out to give the corresponding imines (isolated by converting to the corresponding 2,4-dinitrophenylhydrazones) in 719-3286% yield (recycling number of 10+·BF 4-: 7.2-32.9).
Reductive amination of cyclohexanone in the presence of cyclohexanol over zeolites Hβ and HY
Kirumakki, Sharath R.,Papadaki, Maria,Chary, Komandur V.R.,Nagaraju
, p. 15 - 21 (2010)
Reductive amination of a mixture of cyclohexanone/cyclohexanol in varying proportions has been carried out in the gas phase over zeolites Hβ and HY. The products identified were cyclohexylamine, N-cyclohexylcyclohexanimine, 2-cyclohexen-1-ylcyclohexanone and 2-cyclohexylcyclohexanone. The product distribution during the experiments indicates that cyclohexanol does not undergo reductive amination over acid catalysts; it only forms a condensation product with cyclohexanone. The reaction rates were obtained from experimental data and fit to a kinetic model derived for this reaction. The fits show that this reaction follows a Langmuir-Hinshelwood pathway by the adsorption of both cyclohexanone and the NH3 on the surface of the zeolite.
Synthesis of 5-cyclodecenones via RCM and a three-pot sequence for bisannulation
Curton, Nicholas,Ornelas, Joel,Uhrinak, Abby,Rhem, Brittney,Coulter, Jess,Zhang, Joe,Joyner, P. Matthew,White, James B.
, p. 4061 - 4065 (2016)
5-Cyclodecenones were made by RCM, using the first generation Grubbs catalyst and infinite dilution in refluxing dichloromethane. A convenient one-pot procedure for making 2,6-disubstituted cyclohexanones was developed, which allowed for the synthesis of
NHC-assisted Ni(II)-catalyzed acceptorless dehydronation of amines and secondary alcohols
Takallou, Ahmad,Habibi, Azizollah,Halimehjan, Azim Ziyaei,Balalaie, Saeed
, (2020)
A novel catalytic system including NiCl2-NHC ligand precursor has been developed for the preparation of imines from amines and ketones from alcohols. Owing to the acceptorless dehydrogenation pathway for this reaction, the hydrogen gas is liberated as a by-product. The active catalyst is generated in situ by the reaction of nickel (II) chloride, bis (imidazolium) chlorides and potassium tert-butoxide. The products were obtained in good to excellent yields and a wide variety of amines and ketones were applied successfully in this protocol.
Supported gold-palladium alloy nanoparticle catalyzed tandem oxidation routes to N-substituted anilines from non-aromatic compounds
Taniguchi, Kento,Jin, Xiongjie,Yamaguchi, Kazuya,Mizuno, Noritaka
, p. 14969 - 14972 (2015)
In the presence of a supported gold-palladium alloy nanoparticle catalyst (Au-Pd/Al2O3), various kinds of N-substituted anilines can be synthesized from non-aromatic compounds. The observed catalysis is truly heterogeneous, and Au-Pd/Al2O3 can be reused without a significant loss of its catalytic performance.
First total synthesis of (+)-broussonetine W: Glycosidase inhibition of natural product & analogs
Song, Ying-Ying,Kinami, Kyoko,Kato, Atsushi,Jia, Yue-Mei,Li, Yi-Xian,Fleet, George W. J.,Yu, Chu-Yi
, p. 5157 - 5174 (2016)
The first total synthesis of (+)-broussonetine W (4), a naturally-occurring pyrrolidine iminosugar isolated from the traditional Chinese medical plant Broussonetia kazinoki SIEB (Moraceae), has been completed through a concise synthetic route starting from the readily available d-arabinose derived cyclic nitrone 10 in 11 steps and 31% overall yield, with regioselective installation of the α,β-unsaturated ketone functional group by the elimination of HBr from α-bromoketone as the key step. A number of analogs of (+)-broussonetine W (4) with variable side chain length, different polyhydroxylated pyrrolidine core configurations or saturated cyclohexanones have also been prepared to explore the glycosidase inhibition and the preliminary structure-activity relationship of this intriguing class of compounds. Glycosidase inhibition studies identified the natural product (+)-broussonetine W (4) as a selective and potent inhibitor of β-galactosidase (IC50 = 0.03 μM), while its enantiomer was a selective and potent inhibitor of α-glucosidase (IC50 = 0.047 μM). It was found that the configuration of the polyhydroxylated pyrrolidine ring played a key role on their glycosidase inhibitory activities. The length of side chain and α,β-unsaturated ketone functional group also exhibited some effect on their glycosidase inhibition.
Co-N-C supported on SiO2: A facile, efficient catalyst for aerobic oxidation of amines to imines
Zhang, Chenghui,Zhao, Pengshan,Zhang, Zongliang,Zhang, Jingwei,Yang, Ping,Gao, Peng,Gao, Jun,Liu, Di
, p. 47366 - 47372 (2017)
We developed a novel, facile preparation method of Co-N-C/SiO2, which was the pyrolysis of silicone gel containing metal ion and triethanolamine (TEA) prepared by sol-gel process. N2 adsorption-desorption characterization displayed the sample had high specific surface area and pore volume (220.9 m2 g-1, 0.67 mL g-1). The active Co appeared to be small particles with size of about 5 nm and was well dispersed on SiO2. And the highly dispersed cobalt and nitrogen-doped carbon in Co-N-C/SiO2 served as active phase for the oxidation of amines to imines, thus Co-N-C/SiO2 could efficiently catalyze the oxidation of amines to imines in solvent-free, air atmospheric conditions, avoiding the use of large excesses of additives, specialized oxidant and solvent.
Azobisisobutyronitrile initiated aerobic oxidative transformation of amines: Coupling of primary amines and cyanation of tertiary amines
Liu, Lianghui,Wang, Zikuan,Fu, Xuefeng,Yan, Chun-Hua
, p. 5692 - 5695 (2012)
In the presence of a catalytic amount of radical initiator AIBN, primary amines are oxidatively coupled to imines and tertiary amines are cyanated to α-aminonitriles. These "metal-free" aerobic oxidative coupling reactions may find applications in a wide
Mechanistic study on the ruthenium-catalyzed direct amination of alcohols
Pingen, Dennis,Lutz, Martin,Vogt, Dieter
, p. 1623 - 1629 (2014)
The Ru-catalyzed direct amination of alcohols with ammonia was investigated for the RuHCl(CO)(PPh3)3/Xantphos system in order to gain mechanistic insight. For several Ru(II) precursor complexes the influence of different additives on catalytic performance was investigated. NMR studies revealed that the reaction of RuHCl(CO)(PPh3)3/Xantphos with the alcohol in the presence of a strong base initially formed an inactive dihydrido Ru species. However, by addition of a ketone, the dihydride was (re)activated, where the corresponding imine is the actual activator, formed by immediate condensation of the ketone with ammonia. In the absence of a base, added ketone significantly enhanced catalyst activity. Catalytically inactive RuCl2(PPh3)3 could be activated by base, demonstrating that also complexes without the CO ligand give active catalysts. On the basis of these observations a mechanism was proposed, closely related to known transfer hydrogenation mechanisms.
