19748-13-1Relevant academic research and scientific papers
Cascade [4 + 1] annulation via more environmentally friendly nitrogen ylides in water: Synthesis of bicyclic and tricyclic fused dihydrofurans
Kumar, Atul,Srivastava, Suman,Gupta, Garima
, p. 3269 - 3272 (2012)
A novel imidazolium ylide activated [4 + 1] annulation approach is described for the diastereoselective synthesis of bicyclic and tricyclic fused dihydrofurans in water. This cascade annulation presumably proceeds via a Michael reaction triggered zwitteri
Ionic liquid soluble photosensitizers
Hubbard, Sarah C.,Jones, Paul B.
, p. 7425 - 7430 (2005)
The preparation and investigation of triplet photosensitizers designed to be preferentially soluble in room-temperature ionic liquids are reported. Photosensitizers prepared by covalent attachment of 1-methylimidazole to aryl ketones are soluble in ionic liquids and remain in the ionic liquid layer when the solution is extracted with an organic solvent. The photosensitized isomerization of trans-β-ionol to cis-β-ionol was efficiently carried out in ionic liquid solution with the product ionol being extracted and the sensitizer/ionic liquid mixture being re-used in additional photosensitization reactions. The scope and utility of the sensitizers in sensitizing other reactions are discussed.
DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes
He, Xinwei,Li, Ruxue,Choy, Pui Ying,Liu, Tianyi,Wang, Junya,Yuen, On Ying,Leung, Man Pan,Shang, Yongjia,Kwong, Fuk Yee
supporting information, p. 9444 - 9449 (2020/12/21)
With a tandem DMAP-catalyzed reaction between o-AQM, in which it is generated in situ from propargylic amine, and acyl carbene surrogate (from pyridinium ylide), a variety of polyarylated chromenes are assembled in good yields. This process does not require transition-metal catalyst and exhibits easy manipulation of the arene group and good functional group compatibility, particularly the -Br group which can be further transformed to other functionalities by cross-coupling reactions. The modular feature of o-AQM substrates and the simple operation procedures add further advantages to this synthetic method.
DABCO-catalyzed multi-component domino reactions for the one-pot efficient synthesis of diverse and densely functionalized benzofurans in water
Golchin, Sajedeh,Mosslemin, Mohammad Hossein,Yazdani-Elah-Abadi, Afshin,Shams, Nasim
, p. 1735 - 1749 (2017/02/15)
An efficient, three-component strategy for the improved synthesis of a pharmaceutically interesting diverse kind of multi-functionalized benzofurans via one-pot two-step domino protocol with high diastereoselectivity in excellent yields has been established. The synthesis was achieved by reacting phenacyl bromides, N-heterocycles, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of DABCO (1,4-diazabicyclo[2.2.2]octane) as an inexpensive, impressive, and readily available catalyst in water under reflux. In this process in total three new bonds (two C–C and one C–O) form in one pot. Short reaction time, excellent yields, no chromatographic purification, and evasion of environmentally hazardous or toxic catalysts and organic solvents in the entire reaction process may make this protocol very useful for academia and industry.
A simple approach to pyrrolylimidazole derivatives by azirine ring expansion with imidazolium ylides
Khlebnikov, Alexander F.,Tomashenko, Olesya A.,Funt, Liya D.,Novikov, Mikhail S.
, p. 6598 - 6609 (2014/08/18)
A domino reaction of 2H-azirines with 1-alkyl-3-phenacyl-1H-imidazolium bromides in the presence of Et3N provides a facile route to 1-alkyl-3-(1H-pyrrol-3-yl)-1H-imidazol-3-ium bromides. 1-Benzyl derivatives can be reduced to 1-(1H-pyrrol-3-yl)
Triplet phenacylimidazoliums-catalyzed photocycloaddition of 1,4-dihydropyridines: An experimental and theoretical study
Zhu, Xiaohe,Li, Weipeng,Yan, Hong,Zhong, Rugang
, p. 13 - 20 (2012/08/13)
The photocycloadditions of 1,4-dihydropyridines (DHPs) were achieved by using phenacylimidazoliums (PIms) as photosensitizers. Irradiation of DHPs 3a-g in the presence of PIms 1a-e and 2 performed an efficient formation of 3,9-diazatetraasteranes in shorter times under a lower power lamp. The mechanism of photocycloaddition catalyzed by PIm was studied by laser flash photolysis and theoretical DFT computation. These time-resolved results showed that the triplet excited states of PIms were generated with high efficiency and detected by their characteristic ultraviolet absorptions, which were quenched by DHP at almost diffusion controlled rate. Theoretical studies suggest that PIm is involved in the photocycloaddition process through the 3(DHP? PIm)* triplet complexes and assists the stabilization of intermediates. All subsequent steps are predicted to be favorable and exothermic, leading to the cage dimers.
Regioselective CH bond activation on stabilized nitrogen ylides promoted by Pd(II) complexes: Scope and limitations
Grande, Loreto,Serrano, Elena,Cuesta, Luciano,Urriolabeitia, Esteban P.
scheme or table, p. 394 - 404 (2012/04/23)
The orthopalladation of N-ylides [HxCyN-CHC-(O)Ar] (HxCyN = pyridine, benzylamine, imidazole, aniline, and phenylpyridine; Ar = aryl) has been studied. The incorporation of the Pd atom to these substrates is regioselective, since the orthopalladation is produced, in most of the cases, only at the aryl ring of the benzoyl group with concomitant C-bonding of the Nylide. The X-ray structure of one representative example is reported. Factors governing the observed orientation are discussed, because this regioselectivity is worthy of note, considering the deactivating nature of the carbonyl group. Two exceptions to the general trend have been observed. The first one is the double metalation of the ylide [PhMe2NCHC(O)Ph], which incorporates one Pd at each Ph. The second one is the palladation of the phenylpyridine derivative, which occurs at the pyridinic 2-phenyl ring and produces a six-membered palladacycle.
Synthesis of zwitterionic salts of pyridinium-meldrum acid and barbiturate through unique four-component reactions
Wang, Qi-Fang,Hui, Li,Hou, Hong,Yan, Chao-Guo
supporting information; experimental part, p. 260 - 265 (2010/08/05)
An efficient synthetic procedure for the preparation of the unusual charge-separated pyridinium-Meldrum acid and N,N-dimethylbarbiturate acid zwitterionic salts was developed though a unique one-pot fourcomponent reaction involving pyridine, aromatic aldehyde, Meldrum acid or N,N-dimethylbarbituric acid, and p-nitrobenzyl bromide in acetonitrile. By varying combinations of four components involving nitrogencontaining heterocycles, we conveniently established reactiveα-halomethylene compounds, aldehydes and β-dicarbonyl compounds a library of zwitterionic salts.
Method for treating fibrotic diseases or other indications with imidazolium agents
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, (2008/06/13)
Provided is a method of treating or ameliorating an indication of the invention in an animal, including a human, by administering an effective amount of a compound of the formula I: wherein R1, R2, M, X and Z are as described supra. Also provided are certain imidazolium compounds and pharmaceutical compositions containing the imidazolium compounds.
Method for treating fibrotic diseases or other indications IC
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, (2011/07/06)
Provided, among other things, is a method of treating or ameliorating or preventing an indication of the invention in an animal, including a human comprising administering an effective amount of a compound of the formula I:
