74990-30-0Relevant academic research and scientific papers
Iron-Catalyzed/Mediated C-N Bond Formation: Competition between Substrate Amination and Ligand Amination
Sinha, Suman,Sikari, Rina,Sinha, Vivek,Jash, Upasona,Das, Siuli,Brand?o, Paula,Demeshko, Serhiy,Meyer, Franc,De Bruin, Bas,Paul, Nanda D.
, p. 1935 - 1948 (2019/01/25)
Iron catalyzed carbon-nitrogen bond formation reactions of a wide variety of nucleophiles and aryl halides using well-defined iron-complexes featuring redox noninnocent 2-(arylazo)-1,10-phenanthroline (L1) ligands are reported. Besides substrate centered C-N coupling, C-N bond formation reactions were also observed at the ortho- and para-positions of the phenyl ring of the coordinated azo-aromatic scaffolds affording new tetradentate ligands, 2-N-aryl-(2-arylazo)-1,10-phenanthroline (L2), and tridentate ligands, 4-N-aryl-(2-arylazo)-1,10-phenanthroline (L3), respectively. Control experiments and mechanistic studies reveal that the complex [FeL1Cl2] (1) undergoes in situ reduction during the catalytic reaction to produce the monoanionic complex [1]-, which then acts as the active catalyst. The metal (iron) and the coordinated ligand were found to work in a cooperative manner during the transfer processes involved in the fundamental steps of the catalytic cycle. Detailed experimental and theoretical (DFT) studies were performed to get insight into the competitive substrate versus ligand centered amination reactions.
N-Arylation of heterocycles promoted by tetraethylenepentamine in water
Yang, Qichao,Wang, Yufang,Yang, Li,Zhang, Mingjie
supporting information, p. 6230 - 6233 (2013/07/19)
Tetraethylenepentamine and triethylenetetramine are found to be efficient organic bases for the N-arylation of pyrazole and imidazole with aryl and heteroaryl-iodides and -bromides catalyzed by CuI in water at moderate temperature. The cross-couplings proceed smoothly with good to excellent yields and a variety of functional groups are tolerated under this condition.
C-Glucosides with heteroaryl thiophene as novel sodium-dependent glucose cotransporter 2 inhibitors
Koga, Yuichi,Sakamaki, Shigeki,Hongu, Mitsuya,Kawanishi, Eiji,Sakamoto, Toshiaki,Yamamoto, Yasuo,Kimata, Hirotaka,Nakayama, Keiko,Kuriyama, Chiaki,Matsushita, Yasuaki,Ueta, Kiichiro,Tsuda-Tsukimoto, Minoru,Nomura, Sumihiro
, p. 5561 - 5572 (2013/09/02)
Canagliflozin (1), a novel inhibitor for sodium-dependent glucose cotransporter 2 (SGLT2), has been developed for the treatment of type 2 diabetes. To investigate the effect of replacement of the phenyl ring in 1 with heteroaromatics, C-glucosides 2 were designed, synthesized, and evaluated for their inhibitory activities against SGLT2. Of these, 3-pyridyl, 2-pyrimidyl or 5-membered heteroaryl substituted derivatives showed highly potent inhibitory activity against SGLT2, while 5-pyrimidyl substitution was associated with slightly reduced activity. In particular, 2g (TA-3404) had remarkable anti-hyperglycemic effects in high-fat diet fed KK (HF-KK) mice.
N-aryl pyrazoles: DFT calculations of CH acidity and deprotonative metallation using a combination of lithium and zinc amides
Chevallier, Floris,Halauko, Yury S.,Pecceu, Christelle,Nassar, Ibrahim F.,Dam, To Uyen,Roisnel, Thierry,Matulis, Vadim E.,Ivashkevich, Oleg A.,Mongin, Florence
scheme or table, p. 4671 - 4684 (2011/07/07)
A series of N-aryl and N-heteroaryl pyrazoles have been deproto-metallated using a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination. Mono-, di-, and tri-iodides have been obtained after subsequent trapping with iodine, depending on the s
Iron complex-catalyzed N-arylation of pyrazoles under aqueous medium
Lee, Hang Wai,Chan, Albert S.C.,Kwong, Fuk Yee
experimental part, p. 5868 - 5871 (2010/01/11)
Commercially available FeCl3·6H2O with conformationally rigid diamine ligand is a highly effective catalyst for N-arylation of pyrazoles using aryl and heteroaryl iodides. It is notable to show that this complex is tolerable under aqueous medium and particularly the whole reaction utilizes water as the sole solvent without any additional organic co-solvents and surfactants. Attempted study using other nitrogen nucleophiles is described. This newly developed system provides an alternative protocol to Cu- and Pd-catalyzed N-arylation reactions.
Ligand-free copper-catalyzed N-arylation of nitrogen nucleophiles
Correa, Arkaitz,Bolm, Carsten
, p. 2673 - 2676 (2008/09/19)
Versatile, simple and inexpensive ligand-free, copper-catalyzed N-arylations of sulfoximines and nitrogen-containing heterocycles have been developed affording N-arylated products in high yields.
Magnetic nanoparticle-supported proline as a recyclable and recoverable ligand for the CuI catalyzed arylation of nitrogen nucleophiles
Chouhan, Gagan,Wang, Dashan,Alper, Howard
, p. 4809 - 4811 (2008/09/17)
Magnetic nanoparticle-supported proline ligand was prepared and used for the CuI catalyzed Ullmann-type coupling reactions of aryl/heteroaryl bromides with various nitrogen heterocycles to form the corresponding N-aryl products in good to excellent yields
Mild conditions for copper-catalysed N-arylation of pyrazoles
Cristau, Henri-Jean,Cellier, Pascal P.,Spindler, Jean-Francis,Taillefer, Marc
, p. 695 - 709 (2007/10/03)
Copper-catalysed N-arylation of pyrazoles with aryl or heteroaryl bromides or iodides, which can include functional substituents, was performed under the mildest conditions yet described, with excellent yields and selectivity, by the use as catalyst of a combination of cuprous oxide with a set of inexpensive, chelating oxime-type ligands not previously known to promote such reactions. Other original bi-, tri- or tetradentate ligands providing nitrogen and/or oxygen as chelating atoms were also successfully tested in this type of arylation. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
