50609-88-6Relevant articles and documents
Synthesis and photophysical properties of benzoxazolyl-imidazole and benzothiazolyl-imidazole conjugates
Chen, Hsing-Yu,Huang, He-Shin,Tseng, Tzu-Yu,Yao, Chen-Chen,Yeh, Mei-Yu,Yeh, Yao-Chun
, p. 40228 - 40234 (2021/12/31)
Materials that have higher fluorescence emission in the solid state than molecules in solution have recently been paid more attention by the scientific community due to their potential applications in various fields. In this work, we newly synthesized ben
Structurally Modelling the 2-His-1-Carboxylate Facial Triad with a Bulky N,N,O Phenolate Ligand
Monkcom, Emily C.,de Bruin, Dani?l,de Vries, Annemiek J.,Lutz, Martin,Ye, Shengfa,Klein Gebbink, Robertus J. M.
supporting information, p. 5191 - 5204 (2021/03/01)
We present the synthesis and coordination chemistry of a bulky, tripodal N,N,O ligand, ImPh2NNOtBu (L), designed to model the 2-His-1-carboxylate facial triad (2H1C) by means of two imidazole groups and an anionic 2,4-di-tert-butyl-s
Tuning the optical properties of BODIPY dyes by N-rich heterocycle conjugation using a combined synthesis and computational approach
Banala, Srinivas,Kiessling, Fabian,Merkes, Jean Michel,Ostlender, Tobias,Sun, Haitao,Wang, Fufang
supporting information, p. 19641 - 19645 (2021/11/12)
The increased number of N-atoms induced a blueshift in absorption and a gain in fluorescence quantum yield, from 750 nm and ～0% for pyrrole to 635 nm and ～40% for triazole, respectively. DFT calculations indicated a decrease in HOMO energy levels with the
Formation of exceptionally weak C-C bonds by metal-templated pinacol coupling
Folkertsma,Benthem,Witteman,Van Slagmaat,Lutz,Klein Gebbink,Moret
supporting information, p. 6177 - 6182 (2017/07/10)
The ability of the bis(imidazolyl)ketone ligand BMdiPhIK (bis(1-methyl-4,5-diphenylimidazolyl)ketone) to function as a redox active ligand has been investigated. The reduction of [M(BMdiPhIK)Cl2] (M = Fe and Zn) complexes
Synthesis of optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole rings
Wróblewska, Aneta,Mlostoń, Grzegorz,Heimgartner, Heinz
, p. 1448 - 1452 (2015/12/09)
Optically active polyheterocycles containing pyrrolidine, imidazole, and 1,2,3-triazole units were obtained via a multistep synthesis with the [3+2] cycloaddition of Boc-protected (S)-(pyrrolidin-2-yl)methyl azide with 2-ethynylimidazoles in the presence of CuI (CuAAC reaction) as the key step. Typical for terminal alkynes, the reactions occurred regioselectively and 1,4-disubstituted 1,2,3-triazoles were formed exclusively. The deprotection of the pyrrolidine N-atom was performed by treatment with TFA under standard conditions.
Microwave-assisted conversion of carbonyl compounds into formylated secondary amines: New contribution to the Leuckart reaction mechanism in N-methylformamide
Barba, Fructuoso,Recio, Javier,Batanero, Belen
, p. 1835 - 1838 (2013/04/24)
The reductive amination of several carbonyl compounds (Leuckart reaction) has been performed using N-methylformamide and microwave technology. Under these conditions, a new mechanism is proposed via the initial formation of an imine, followed by reduction
Ruthenium piano-stool complexes bearing imidazole-based PN ligands
Kunz, Peter C.,Thiel, Indre,Noffke, Anna Louisa,Rei?, Guido J.,Mohr, Fabian,Spingler, Bernhard
supporting information; experimental part, p. 33 - 40 (2012/01/06)
A variety of piano-stool complexes of cyclopentadienyl ruthenium(II) with imidazole-based PN ligands have been synthesized starting from the precursor complexes [CpRu(C10H8)]PF6, [CpRu(NCMe) 3]PF6 and [CpRu(PPh3)2Cl]. PN ligands used are imidazol-2-yl, -4-yl and -5-yl phosphines. Depending on the ligand and precursor different types of coordination modes were observed; in the case of polyimidazolyl PN ligands these were κ1P-monodentate, κ2P,N-, κ2N,N- and κ3N,N,N- chelating and μ-κP:κ2N,N-brigding. The solid-state structures of [CpRu(1a)2Cl ]·H2O (5 .H2O) and [{CpRu(μ-κ2-N,N- κ'1-P-2b)}2](C6H5PO 3H)2(C6H5PO3H 2)2, a hydrolysis product of the as well determined [{CpRu(2b)}2](PF6)2.2CH 3CN (7b.2CH3CN) were determined (1a = imidazol-2-yldiphenyl phosphine, 2b = bis(1-methylimidazol-2-yl)phenyl phosphine, 3a = tris(imidazol-2-yl)phosphine). Furthermore, the complexes [CpRu(L)2]PF6 (L = imidazol-2-yl or imidazol-4-yl phosphine) have been screened for their catalytic activity in the hydration of 1-octyne.
Asymmetric Copper(II)-catalysed nitroaldol (Henry) reactions utilizing a chiral C1-symmetric dinitrogen ligand
Zhou, Yirong,Gong, Yuefa
experimental part, p. 6092 - 6099 (2011/11/29)
A series of stable chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensation of chiral amines [(-)-exo-bornylamine or (+)-(1S,2S,5R)-menthylamine] with various substituted imidazolecarbaldehydes. With the assistance of base, the ligand L1 in combination with CuCl2·2H2O (2.5 mol-% or 5.0 mol-%) can efficiently promote nitroaldol (Henry) reactions between a variety of aldehydes and nitromethane. Both aromatic and aliphatic aldehydes were tolerated in our catalytic system, affording the expected nitroalcohol products in high yields (up to 97%) and with good enantioselectivities (up to 96%) under mild reaction conditions. A series of chiral C1-symmetric dinitrogen ligands were conveniently synthesized in high yields by condensations of chiralamines with various substituted imidazolecarbaldehydes. The ligand L1 in conjunction with CuCl2·2H2O can efficiently promote nitroaldol (Henry) reactions between various aldehydes and nitromethane in high yields (up to 97%) and with good enantioselectivities (up to 96%).
Regioselective synthesis of 4,5-diaryl-1-methyl-1H-imidazoles including highly cytotoxic derivatives by Pd-catalyzed direct C-5 arylation of 1-methyl-1H-imidazole with aryl bromides
Bellina, Fabio,Cauteruccio, Silvia,Di Fiore, Annarita,Rossi, Renzo
experimental part, p. 5436 - 5445 (2009/05/07)
A general and efficient three-step procedure for the highly regioselective synthesis of 1-methyl-1H-imidazoles possessing electron-rich, electron-neutral, and/or electron-deficient aryl moieties at their 4- and 5-positions is described. The first step involves the Pd-catalyzed direct C-5 arylation of commercially available 1-methyl-1H-imidazole with aryl bromides, and the second and third steps of the sequence involve the selective C-4 bromination of the resulting 5-aryl-1-methyl-1H-imidazoles with NBS, followed by a PdCl 2(dppf)-catalyzed Suzuki-type reaction between 5-aryl-4-bromo-1- methyl-1H-imidazoles and arylboronic acids under phase-transfer conditions. Two 4,5-diaryl-1-methyl-1H-imidazoles so prepared, which can be regarded as Z-restricted analogues of naturally occurring combretastatin A-4 (CA-4), proved to be highly cytotoxic against a variety of human tumor cell lines, and one of these derivatives has been shown to be more cytotoxic than CA-4 and all of the imidazole derivatives investigated in the literature thus far. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Design and novel synthesis of aryl-heteroaryl-imidazole MAP kinase inhibitors
Dobler, Markus R.
, p. 7115 - 7117 (2007/10/03)
Inhibitors of the MAP kinase p38, potentially useful for the treatment of rheumatoid arthritis and inflammatory diseases, were found to exhibit antifungal activity. We have developed a new diversity-oriented strategy leading to concise and efficient syntheses of known and new members of this compound class. The strategy is based on carbon-carbon cross-coupling reactions using N-protected 4,5-diiodo-imidazoles as the starting templates.
