21352-19-2Relevant articles and documents
Synthesis and indole coupling reactions of azetidine and oxetane sulfinate salts
Nassoy, Anne-Chloé M. A.,Raubo, Piotr,Harrity, Joseph P. A.
, p. 5914 - 5916 (2015)
Aztidine and oxetane sulfinate salts are easily prepared from commercially available 3-iodoheterocycle precursors in a three-step sequence. They undergo smooth coupling reactions thereby providing an expedient route for the introduction of these four-membered heterocycles into indoles.
Benzoheterocycle compound and application thereof
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Paragraph 0117-0120, (2021/06/09)
The invention discloses benzo-heterocyclic type compounds and application thereof, and particularly provides a compound shown in a formula (I) in the text. An extraction agent composed of the type ofcompounds has a high extraction rate towards lithium ion
SMALL MOLECULE INHIBITORS OF DYRK/CLK AND USES THEREOF
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Paragraph 1110-1111, (2020/02/19)
This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a 6,5-heterocyclic structure (e.g., compounds having a imidazopyridine, imidazopyrimidine, imidazopyrazine, imidazopyridazine, imidazotriazine, benzoimidazole, benzotriazole, benzoisoxazole, purine, indazole, triazolotriazine, triazolopyridazine, triazolopyrimidine, triazolopyrazine, triazolotetrazine, triazolopyridine, pyrazolopyrazine, pyrazolopyrimidine, pyrazolopyridazine, pyrazolotriazine, pyrazolopyridine, isoxazolopyrazine, isoxazolopyrimidine, isoxazolopyrdiazine, isoxazolotriazine, or isoxalopyridine structure) which function as inhibitors of DYRK1A, DYRK1B, and Clk-1, and their use as therapeutics for the treatment of Alzheimer's disease, Down syndrome, diabetes, glioblastoma, autoimmune diseases, cancer (e.g., glioblastoma, prostate cancer), inflammatory disorders (e.g., airway inflammation), and other diseases.
A Four-Step Synthesis of (±)-γ-Lycorane via Pd0-Catalyzed Double C(sp2)-H/C(sp3)-H Arylation
Rocaboy, Ronan,Dailler, David,Baudoin, Olivier
supporting information, p. 772 - 775 (2018/02/09)
An expedient synthesis of lycorine alkaloids is reported using a palladium(0)-catalyzed double C-X/C-H arylation as the key step. The selectivity of this reaction was controlled through the judicious choice of the two halogen atoms, and its generality was
A new transformation of aminopyridines upon diazotization in acetonitrile with the formation of N-pyridinylacetamides
Chudinov,Dovbnya,Krasnokutskaya,Ogorodnikov,Filimonova
, p. 2312 - 2314 (2017/05/12)
Diazotization of aminopyridines upon treatment with NaNO2 and H3PO4 in acetonitrile led to the formation of N-pyridinylacetamides. This reaction constitutes a convenient and general preparative method for the synthesis of 2-, 3-, and 4-N-pyridinylacetamides under mild conditions in good yields. The in situ oxidation of the thus obtained N-pyridinylacetamides with hydrogen peroxide gave good yields of pyridinylacetamide N-oxides.
Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
supporting information, p. 197 - 209 (2015/03/03)
In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
Bisguanidines with biphenyl, binaphthyl, and bipyridyl cores: Proton-sponge properties and coordination chemistry
Maronna, Astrid,Huebner, Olaf,Enders, Markus,Kaifer, Elisabeth,Himmel, Hans-Joerg
, p. 8958 - 8977 (2013/07/25)
Herein, we report on the synthesis, protonation, and coordination chemistry of chelating guanidine ligands with biphenyl, binaphthyl, and bipyridyl backbones. The ligands are shown to be proton sponges, and this protonation was studied experimentally and by using quantum-chemical calculations. Group 10 metal (Ni, Pd, and Pt) complexes with different metal/ligand ratios were synthesized. In the case of the bipyridyl systems, coordination occurs exclusively at the pyridine N atoms, as opposed to protonation. The spin-density distribution and the magnetism were evaluated for a series of paramagnetic NiII complexes with the aid of paramagnetic NMR spectroscopic studies in alliance with quantum-chemical calculations and magnetic (SQUID) measurements. Through direct delocalization from the singly occupied molecular orbitals (SOMOs), a significant amount of spin density is placed on the guanidinyl groups, and spin polarization also transports spin density onto the aromatic backbone. Showing some backbone: Bisguanidines with flexible biaryl backbones are proton sponges and ligands in a series of new mono- and dinuclear Group 10 metal complexes (see figure). The spin-density distribution in paramagnetic NiII complexes was studied by using NMR spectroscopy and quantum-chemical calculations. Copyright
CERTAIN TRIAZOLOPYRIDINES AND TRIAZOLOPYRAZINES, COMPOSITIONS THEREOF AND METHODS OF USE THEREFOR
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Page/Page column 23, (2012/10/08)
Provided are certain triazolopyridines and triazolopyrazines, compositions thereof and methods of use therefor.
A palladium-catalyzed regiospecific synthesis of N-aryl benzimidazoles
Zheng, Nan,Anderson, Kevin W.,Huang, Xiaohua,Nguyen, Hanh Nho,Buchwald, Stephen L.
, p. 7509 - 7512 (2008/09/17)
(Chemical Equation Presented) Highly tolerated: A catalytic method employing [Pd2(dba)3] and XPhos or RuPhos permits the efficient synthesis of N-aryl benzimidazoles in regioisomerically pure form starting from ortho-halo-anilides (see scheme), and tolerates a wide range of functional groups, dba = trans,trans-dibenzylideneacetone.
The coordination chemistry of 3,3′-diamino-2,2′-bipyridine and its dication: Exploring the role of the amino groups by x-ray crystallography
Rice, Craig R.,Onions, Stuart,Vidal, Natalia,Wallis, John D.,Senna, Maria-Cristina,Pilkington, Melanie,Stoeckli-Evans, Helen
, p. 1985 - 1997 (2007/10/03)
The synthesis and structural chemistry of a series of new divalent transition metal complexes of the bis-bidentate ligand 3,3′-diamino-2,2′-bipyridine (L1) and its dication L1H2 are described. Ligand L1 reacts with salts of divalent transition metals to afford the (1:1) metal-ligand complexes (2a-2d) as well as the tris complexes (3a-3f). All complexes were fully characterised by spectroscopic methods and the following compounds [Cu(L1)Cl2]2 (2a), [Cu(L1)(OAc)2] (2b), [Zn(L1)3][OTf]2 (3a), and [Zn(L1)3][ZnCl4] (3e and 3f) were structurally characterised. Results from single crystal X-ray diffraction measurements indicate that formation of an intra-molecular hydrogen bond between the two amino groups allows the ligand to coordinate divalent metal ions through their diimine binding sites. Furthermore, the structure of compound 2a reveals that it crystallises as a dimer in which each copper ion is bound to two pyridine nitrogen atoms and two chloride ions in a distorted square planar arrangement, with a long axial contact from a neighbouring amino group completing the approximately square-pyramidal geometry at CuII. Complexation of this ligand in acidic conditions afforded the compound [Cu(L1H2)Cl4] (4), as well as the two salts [L1H2][CuCl4] (5a) and [L1H2][ZnCl4] (5b). All three compounds have been structurally characterised and results indicate that the dication (L1H2) displays a different coordination preference for the chelation of metal ions. In all three cases, both of the heterocyclic N atoms of the ligand are protonated, thus preventing chelation to the metal ion, although for compound 4 crystallographic studies reveal that the two amino functionalities coordinate the copper(II) ion. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
