15813-09-9Relevant articles and documents
Selective functionalization of imidazoles via an iodine-copper exchange reaction
Yang, Xiaoyin,Knochel, Paul
, p. 2170 - 2172 (2006)
The reaction of protected 4,5-diiodoimidazoles with (PhMe 2CCH2)2CuLi regioselectively provides 5-cuprated imidazoles, which readily react with various electrophiles furnishing functionalized imidazoles in good yields; remarkably, these resulting mono-iodoimidazoles undergo again an iodine-copper exchange reaction in the presence of sensitive functional groups, like an aldehyde or a ketone. The Royal Society of Chemistry 2006.
Scope and Mechanistic Limitations of a Sonogashira Coupling Reaction on an Imidazole Backbone
Sandtorv, Alexander H.,Bj?rsvik, Hans-René
, p. 4658 - 4666 (2015)
A Sonogashira coupling reaction method to join terminal alkynes to the imidazole backbone was developed and investigated. The method exhibits good functional group tolerance and provides target 4-alkynylated imidazoles in 70-93% yield. The alkyne reagents were characterized by means of DFT calculations, from which electrostatic potential surfaces (EPS) were produced. A clear correlation between the EPS of the triple bond and the success of the coupling reaction was revealed. If the EPS is in range -94 to -105 kJmol-1 the coupling is successful. An unsuccessful class of reagents (alkynols) was made compatible by means of an auxiliary group (tert-butyldimethylsilyl). EPSs of these modified reagents then resembled those of the model and these auxiliary-assisted reagents then coupled successfully in excellent yields.
Efficient iodination of aromatic compounds using potassium ferrate supported on montmorillonite
Keipour, Hoda,Khalilzadeh, Mohammad A.,Mohtat, Bita,Hosseini, Abolfazl,Zareyee, Daryoush
, p. 1427 - 1430 (2011)
Potassium ferrate impregnated on montmorillonite is a mild, cheap, and non-toxic reagent for the iodination of phenols, including naphthol, aromatic amines, and heterocyclic substrates in fair to excellent yields by a simple isolation procedure.
Synthesis of imidazolo[5,4-b]carbazole-4,10-quinones
Desforges, Gwéna?lle,Bossert, Cécile,Montagne, Cyril,Joseph, Beno?t
, p. 1306 - 1308 (2004)
The preparation of imidazolo[5,4-b]carbazole-4,10-quinones 9 is described. The key steps of the synthesis are selective halogen-metal exchanges on the imidazole 3 and subsequent addition to carbonyl groups of ethyl-3-formylindole- 2-carboxylate 4.
A comparative study of tricarbonylmanganese photoactivatable CO releasing molecules (PhotoCORMs) by using the myoglobin assay and time-resolved IR spectroscopy
Huber, Wilhelm,Linder, Rolf,Niesel, Johanna,Schatzschneider, Ulrich,Spingler, Bernhard,Kunz, Peter C.
, p. 3140 - 3146 (2012)
Tricarbonylmanganese(I) complexes of the ligands tris(imidazol-4-yl) phosphane (4-tipH), tris(1,4-diisopropylimidazol-2-yl)phosphane (2-tipiPr2), tris(pyridin-2-yl)phosphane (tpp) and tris(N-methylimidazol-2-yl)carbinol (2-ticNMe) were prepared. These act as N,N,N tripodal chelators. The solid-state structure of [Mn(CO) 3(tpp)]OTf was determined by X-ray diffraction. The potential of these complexes to act as photoactivatable CO-releasing molecules (PhotoCORMs) was studied with the UV/Vis spectroscopy-based myoglobin assay as well as by time-resolved IR spectroscopy. Within the series of compounds prepared, the steric bulk of the imidazolyl groups seems to significantly influence the CO-release kinetics and stoichiometry when using the myoglobin assay. In contrast, the time-resolved IR data suggest release of all carbonyl ligands upon irradiation. This effect points to a much closer association of myoglobin and PhotoCORMs than previously thought and will require further investigation.
Modular synthesis of helicene-like compounds based on the imidazolium motif
?í?ková, Martina,?aman, David,Koval, Du?an,Ka?i?ka, Václav,Klepetá?ová, Blanka,Císa?ová, Ivana,Teply, Filip
, p. 5681 - 5685 (2014)
Straightforward synthesis of novel mono- and tricationic helical compounds based on the imidazolium core has been developed. The synthetic route based on double [2+2+2] cycloaddition reactions of precursors with the imidazolium core motif is notably modular and reaches beyond established protocols used for the synthesis of imidazolium systems as well as beyond the reported protocols used to assemble compounds with helical frameworks. This approach opens rapid four-step access to a cationic species featuring nine orthoannulated rings that represents the highest order helical nitrogen-based cationic system reported to date.
Synthesis of Complexes with Abnormal "protic" N-Heterocyclic Carbenes
Jin, Hanpeng,Tan, Tristan Tsai Yuan,Hahn, F. Ekkehardt
, p. 13811 - 13815 (2015)
Neutral 4-iodo-N-ethylimidazole 3 oxidatively adds to [Pt(PPh3)4] to give, in the presence of different tetraalkylammonium salts, complexes trans-[4], trans-[5], and trans-[6] containing an anionic C4-bound heterocycle with an unsubstituted ring-nitrogen atom. Complex trans-[4] reacts with the proton source NH4I under protonation of the ring-nitrogen atom to produce complex trans-[7]I which bears an NH,NR-substituted aNHC ligand. The reaction of trans-[4] with CH3I yields the complex trans-[8]I which has a classical aNHC ligand with two alkylated ring-nitrogen atoms.
Metal-mediated base pairing in DNA involving the artificial nucleobase imidazole-4-carboxylate
Sandmann, Nikolas,Defayay, Denise,Hepp, Alexander,Müller, Jens
, p. 85 - 93 (2019)
The use of imidazole-4-carboxylate (X) as an artificial nucleobase in metal-mediated base pairing is reported. Towards this end, the corresponding deoxyribonucleoside was synthesized and structurally characterized as its sodium salt (sodium 1,2-dideoxy-1-(4-carboxyimidazol-1-yl)-D-ribofuranose). The deoxyribonucleoside was incorporated into different DNA duplexes (parallel-stranded and antiparallel-stranded), and their Cu(II)- and Ag(I)-binding behavior was investigated. It was shown that both X–Cu(II)–X and X–Ag(I)–X base pairs can be formed, with the former being more stabilizing than the latter. The formation of an X–Cu(II)–X base pair is accompanied by an increase in the duplex melting temperature of approximately 20 °C for antiparallel-stranded duplexes and of 12 °C for the parallel-stranded duplex under investigation. Imidazole-4-carboxylate represents the first imidazole-based nucleoside for Cu(II)-mediated base pairing. Moreover, it is the smallest nucleoside known to form stable Cu(II)-mediated base pairs. Structures of the X–Cu(II)–X and X–Ag(I)–X base pairs are proposed, too, based on molecular structures obtained using the model nucleobase 1-benzyl-1H-imidazole-4-carboxylate.
Synthesis method of 4, 5-diiodo-1H-imidazole
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Paragraph 0008-0009, (2021/02/06)
The invention relates to a synthetic method of 4, 5-diiodo-1H-imidazole. The technical problem that the solubility of raw materials is poor during synthesis of 4, 5-diiodo-1H-imidazole is mainly solved. The synthesis method comprises the following steps: under ice bath cooling, reacting imidazole with sodium hydroxide to generate imidazole sodium, and continuously reacting an intermediate with elemental iodine dissolved in tetrahydrofuran to generate a target compound. As a fine chemical product and a medical intermediate, the 4, 5-diiodo-1H-imidazole is widely applied to the fields of material chemistry, catalytic chemistry and pharmacy.
Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A
Zhou, Qingqing,Reekie, Tristan A.,Abbassi, Ramzi H.,Indurthi Venkata, Dinesh,Font, Josep S.,Ryan, Renae M.,Munoz, Lenka,Kassiou, Michael
, p. 5852 - 5869 (2018/11/10)
Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.
