4471-09-4Relevant articles and documents
Sulfated polyborate: A dual catalyst for the reductive amination of aldehydes and ketones by NaBH4
Ganwir, Prerna,Chaturbhuj, Ganesh
supporting information, (2021/05/19)
An efficient, quick, and environment-friendly one-pot reductive amination of aldehydes or ketones was developed. In ethanol at 70 °C, a imination catalyzed by sulfated polyborate and further reduced by sodium borohydride yields various amines. The present method has many significant benefits, including a shorter reaction time, excellent yields, and a hassle-free, straightforward experimental process. The reaction has a wide range of applications due to its flexibility, including secondary amine for reductive amination.
Large-Scale Synthesis of 2-Chlorotetrahydroquinoline and 2-Chlorotetrahydroquinolin-8-one
Zong, Zhijian,Wu, Ke,Jin, Liqun,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
, p. 3675 - 3683 (2020/09/21)
An efficient large-scale preparation of 2-chlorotetrahydroquinoline with cyclohexanone and benzylamine as starting materials was developed and well optimized, in which benzyl-protected enamide was successfully cyclized and benzyl group was directly removed under Vilsmeier conditions. Azeotropic distillation provided 264 g of 2-chlorotetrahydroquinoline (79%) on a 2 mol scale of reaction without intermediate isolation. The downstream product 2-chlorotetrahydroquinolin-8-one was acquired through Boekelheide rearrangement, hydrolysis of acetate via NaBH 4reduction, and Anelli oxidation. With the developed procedure, the intermediates were not necessary to be isolated and 2-chlorotetrahydroquinolin-8-one was conveniently obtained with solvent slurry in 65% overall isolated yield in a four-step sequence.
Asymmetric Synthesis of Six-Membered Cyclic Sulfamides via Palladium-Catalyzed Alkene Carboamination Reactions
Garlets, Zachary J.,Wolfe, John P.
, p. 4444 - 4452 (2018/05/28)
The asymmetric synthesis of six-membered cyclic sulfamides via palladium-catalyzed alkene carboamination reactions of N -homoallylsulfamides with aryl halides is described. High levels of enantioselectivity were obtained with a catalyst composed of Pd 2 dba 3 and (S)-Siphos-PE.
Substituted pyrimidinetrione compound, composition containing same and application of substituted pyrimidinetrione compound
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Paragraph 0108; 0111-0113, (2018/11/22)
The invention provides a substituted pyrimidinetrione compound, a composition containing the same and application of the substituted pyrimidinetrione compound. The invention discloses the pyrimidinetrione compound as shown in formula (I) or the crystal form, pharmaceutically acceptable salt, prodrug, stereisomer, hydrate or solvent compound thereof. The pyrimidinetrione compound and the composition containing the same can be used for regulating hypoxia-inducible factors (HIF) and/or erythropoietin (EPO) and can be used for preparing medicine for regulating and controlling human body anemia.
Cobalt-Catalyzed Cross-Coupling of α-Bromo Amides with Grignard Reagents
Barde,Guérinot,Cossy
supporting information, p. 6068 - 6071 (2017/11/28)
A cobalt-catalyzed cross-coupling between α-bromo amides and Grignard reagents is disclosed. The reaction is general and allows access to a large variety of α-aryl and β,γ-unsaturated amides. Some mechanistic investigations have been undertaken to determine the nature of the intermediate species.
Short Total Synthesis of (±)-γ-Lycorane by a Sequential Intramolecular Acylal Cyclisation (IAC) and Intramolecular Heck Addition Reaction
Monaco, Alessandra,Szulc, Blanka R.,Rao, Zenobia X.,Barniol-Xicota, Marta,Sehailia, Moussa,Borges, Bruno M. A.,Hilton, Stephen T.
supporting information, p. 4750 - 4755 (2017/04/14)
An intramolecular acylal cyclisation (IAC) approach to the synthesis of a range of bicyclic heterocycles is reported. As an example of the utility of the IAC reaction, the methodology was applied in a protecting-group-free five-step total synthesis of (±)-γ-lycorane, incorporating a new intramolecular Heck addition reaction to generate the pentacyclic core structure of the natural product in good yield.
Iridium(I) Complexes Bearing a Noninnocent PNP-Pincer-Type Phosphaalkene Ligand: Catalytic Application in the Base-Free N-Alkylation of Amines with Alcohols
Chang, Yung-Hung,Tanigawa, Ippei,Taguchi, Hiro-Omi,Takeuchi, Katsuhiko,Ozawa, Fumiyuki
, p. 754 - 760 (2016/03/01)
A series of IrI complexes [Ir(L)(PPEP?)] [L = Cl- (3), CO (4), tBuNC (5), PMe3 (6), PPh3 (7)], coordinated with a PNP-pincer-type phosphaalkene ligand bearing a dearomatized pyridine ring (PPEP?), have been prepared and their catalytic properties for the dehydration/condensation of amines with alcohols has been examined. The catalytic reactions successfully proceed under base-free conditions to give N-alkylated amines and their dehydrogenation derivatives (imines). The product selectivity is dependent on L coordinated with Ir(PPEP?). Complexes 4 and 5 that contain π-accepting ligands (CO, tBuNC) form N-alkylated amines as the major products in a closed system using a nitrogen-gas-filled Schlenk tube. In contrast, complex 7 that contain PPh3 as L produces imines as the major products under a nitrogen-gas flow. The reason for the selectivity change depending on L is discussed based on stoichiometric reactions using model compounds of presumed catalytic intermediates. PNP-pincer-type phosphaalkene complexes of IrI bearing a dearomatized pyridine ring have been found to catalyze the dehydration/condensation of amines with alcohols under base-free conditions to afford N-alkylated amines and imines in high yields. The product selectivity can be controlled by the choice of auxiliary ligands (L) as well as the reaction conditions.
NOVEL PROCESS FOR THE PREPARATION OF SPIROHETEROCYCLIC PYRROLIDINE DIONES
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Page/Page column 59; 60, (2015/02/02)
A process for making certain spiroheterocyclic pyrrolidine dione derivatives.
Phosphoric acid mediated tautomerism of imines: Addition of a secondary enamine intermediate to aldehydes
Davis, Lindsey O.,Putri, Marcella A.,Meyer, Caitlin L.,Durant, Christopher P.
, p. 3100 - 3103 (2014/05/20)
A phosphoric acid derivative has been shown to promote the addition between an imine and several aldehyde substrates through an enamine intermediate to give cross-aldol condensation products. The reaction scope and preliminary mechanistic investigations will be presented.
Transition state analysis of enantioselective br?nsted base catalysis by chiral cyclopropenimines
Bandar, Jeffrey S.,Sauer, Gregory S.,Wulff, William D.,Lambert, Tristan H.,Vetticatt, Mathew J.
supporting information, p. 10700 - 10707 (2014/08/18)
Experimental 13C kinetic isotope effects have been used to interrogate the rate-limiting step of the Michael addition of glycinate imines to benzyl acrylate catalyzed by a chiral 2,3-bis(dicyclohexylamino) cyclopropenimine catalyst. The reaction is found to proceed via rate-limiting carbon-carbon bond formation. The origins of enantioselectivity and a key noncovalent CH?O interaction responsible for transition state organization are identified on the basis of density functional theory calculations and probed using experimental labeling studies. The resulting high-resolution experimental picture of the enantioselectivity-determining transition state is expected to guide new catalyst design and reaction development.
