25700-16-7Relevant academic research and scientific papers
Rhodium and iridium complexes with chelating C-C′-imidazolylidene- pyridylidene ligands: Systematic approach to normal, abnormal, and remote coordination modes
Segarra, Candela,Mas-Marza, Elena,Mata, Jose A.,Peris, Eduardo
, p. 5169 - 5176 (2012)
A series of linked imidazolium-pyridinium salts ([Him-pyH](X)2) have been used as imidazolylidene-pyridylidene ligand precursors for the preparation of rhodium(III) and iridium(III) complexes. The relative configuration of the [Him-pyH](X)2 salts determines whether the coordination of the pyridylidene occurs through the normal, abnormal, or remote form. In order to obtain complexes with the imidazolylidene part of the ligand coordinated through the abnormal form, salts with the C2 position of the imidazolium blocked with a methyl group were used, although the products resulting from the C-H aliphatic activation of the methyl group or the C-C cleavage of the C2-Me bond were obtained instead. The crystallographic study of three molecules allowed us to evaluate the relative trans influence of the normal, abnormal, and remote coordination forms of the pyridylidene and also to compare it to the trans influence provided by the imidazolylidene.
Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition
Abou-Shehada, Sarah,Teasdale, Matthew C.,Bull, Steven D.,Wade, Charles E.,Williams, Jonathan M. J.
, p. 1083 - 1087 (2015/03/30)
A clean, mild and sustainable method for the functionalization of pyridines and their analogues is reported. A zinc-based Lewis acid is used to activate pyridine and its analogues towards nucleophilic aromatic substitution, conjugate addition, and cyclization reactions by binding to the nitrogen on the pyridine ring and activating the pyridine ring core towards further functionalization.
Ligand-free Cu2O-catalyzed cross coupling of nitrogen heterocycles with iodopyridines
Teo, Yong-Chua,Yong, Fui-Fong,Sim, Shirlyn
, p. 7279 - 7284 (2013/08/23)
A practical and efficient strategy has been developed for the cross coupling of nitrogen heterocycles with halopyridines using ligand-free Cu 2O as catalyst and Cs2CO3 as the base. The protocol is applicable to a series of highly functionalised heterocycles, such as 7-azaindole, indazole, indole, imidazole, pyrrole and pyrazole, affording the N-heteroaryl derivatives in high yields (up to 96%).
Facile and scalable preparation of 2-imidazolylpyridines
Raba, Andreas,Anneser, Markus R.,Jantke, Dominik,Cokoja, Mirza,Herrmann, Wolfgang A.,Kühn, Fritz E.
supporting information, p. 3384 - 3387 (2013/07/11)
A novel method for the synthesis of 2-imidazolylpyridines is presented. The reaction of 2-halopyridines, potassium carbonate, and imidazole at high temperatures under inert gas atmosphere leads exclusively to the formation of 2-imidazolylpyridines in high yields. The synthesis is scalable, comparatively inexpensive, and the products are easily isolable.
A convenient synthesis of (1 H-azol-1-yl)piperidines
Shevchuk, Nadiia V.,Liubchak, Kostiantyn,Nazarenko, Kostiantyn G.,Yurchenko, Aleksandr A.,Volochnyuk, Dmitriy M.,Grygorenko, Oleksandr O.,Tolmachev, Andrey A.
experimental part, p. 2041 - 2048 (2012/08/07)
A convenient preparation of 3- and 4-(1H-azol-1-yl)piperidines by arylation of azoles (i.e., pyrazoles, imidazoles, and triazoles) with 3- and 4-bromopyridines and subsequent reduction of the pyridine ring was developed. The method was extended to benzo analogues of the title compounds. Georg Thieme Verlag Stuttgart · New York.
One-step conversion of azine N -oxides to α-1,2,4-triazolo-, 1,2,3-triazolo, imidazolo-, and pyrazoloheteroarenes
Keith, John M.
supporting information; experimental part, p. 2722 - 2725 (2010/07/17)
Pyridine, quinoline, isoquinoline, azaindole, and pyrimidine N-oxides were converted to their α-triazole and α-diazole derivatives by treatment with the corresponding p-toluenesulfonylazoles and Hunigs base at elevated temperatures.
One step conversion of heteroaromatic-N-oxides to imidazolo-heteroarenes
Keith, John M.
, p. 327 - 330 (2008/04/12)
(Chemical Equation Presented) Various pyridine-, quinoline-, isoquinoline-, and pyrimidine-N-oxides were converted to their corresponding α-imidazoloheteroarenes in good yield by treatment with sulfuryl diimidazole in nonpolar solvents at elevated tempera
N-arylation of heterocycles with activated chloro- and fluoroarenes using nanocrystalline copper(II) oxide
Kantam, M. Lakshmi,Yadav, Jagjit,Laha, Soumi,Sreedhar, Bojja,Jha, Shailendra
, p. 1938 - 1942 (2008/09/16)
Nanocrystalline copper oxide was found to be an effective heterogeneous catalyst for the N-arylation of heterocycles with activated chloro- and fluoroarenes using potassium carbonate as base. N-Arylated products were isolated in good to excellent yields. The catalyst can be used for five cycles with almost consistent activity.
Copper fluorapatite catalyzed N-arylation of heterocycles with bromo and iodoarenes
Lakshmi Kantam,Venkanna,Sridhar,Shiva Kumar
, p. 3897 - 3899 (2007/10/03)
Copper exchanged fluorapatite (CuFAP) is an effective heterogeneous catalyst for N-arylation of heterocycles with bromo- or iodoarenes using K2CO3 as base. N-Arylated products were isolated in good to excellent yields, demonstrating the versatility of the reaction.
Synthesis of Cu2O coated Cu nanoparticles and their successful applications to Ullmann-type amination coupling reactions of aryl chlorides
Son, Seung Uk,Park, In Kyu,Park, Jongnam,Hyeon, Taeghwan
, p. 778 - 779 (2007/10/03)
We synthesized uniform Cu2O coated Cu nanoparticles from the thermal decomposition of copper acetylacetonate followed by air oxidation and used these nanoparticles as catalysts for Ullmann type amination coupling reactions of aryl chlorides.
