61209-74-3Relevant academic research and scientific papers
Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
Galloway, Jordan D.,Mai, Duy N.,Baxter, Ryan D.
supporting information, p. 5772 - 5775 (2017/11/10)
A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.
One-Pot Reactions for Modular Synthesis of Polysubstituted and Fused Pyridines
Song, Zhidong,Huang, Xin,Yi, Wenbin,Zhang, Wei
, p. 5640 - 5643 (2016/11/17)
A 2-fluoro-1,3-dicarbonyl-initiated one-pot Michael addition/[5 + 1] annulation/dehydrofluorinative aromatization reaction sequence is introduced for regioselective synthesis of di-, tri-, tetra-, and pentasubstituted pyridines as well as fused pyridines. This simple and modular synthesis is performed using readily available starting materials and under transition-metal catalyst-free conditions.
Substrate Control in the Gold(I)-Catalyzed Cyclization of β-Propargylamino Acrylic Esters and Further Transformations of the Resultant Dihydropyridines
Miku?ek, Ji?í,Matou?, Petr,Matou?ová, Eli?ka,Janou?ek, Martin,Kune?, Ji?í,Pour, Milan
, p. 2912 - 2922 (2016/09/19)
N-Protected β-propargylamino acrylic esters with a push-pull olefinic bond afforded good to high yields of dihydropyridines upon treatment with 5% tris(2-furyl)phosphine-gold(I) chloride/silver(I) tetrafluoroborate [(TFP)AuCl/AgBF4] in anhydrous benzene. Carbamate and sulfonyl groups were employed for nitrogen protection. On a model enyne, the p-methoxybenzenesulfonyl (MBS) group was found to be a better protective group than tosyl in terms of cyclization yield, and also the yield of elimination to the corresponding 2,3,4-trisubstituted pyridines. Boc-protected dihydropyridines underwent partial deprotection/oxidation under the cyclization conditions, which enabled a more straightforward, one-pot preparation of the corresponding pyridines. In another application, an appropriately substituted derivative protected as a stable methoxycarbamate was subjected to catalytic hydrogenation affording the known precursor of paroxetine. The chemoselectivity of enyne cyclization (dihydropyridine vs. pyrrole) is governed, among other factors, by C-3 substitution. Dihydropyridines were obtained as sole products regardless of the catalyst/conditions when C-3 was unsubstituted. (Figure presented.).
A heavy metal- and oxidant-free, one-pot synthesis of pyridines and fused pyridines based on a Lewis acid-catalyzed multicomponent reaction
Raja, V. P. Alex,Tenti, Giammarco,Perumal, Subbu,Menndez, J. Carlos
, p. 12270 - 12272 (2015/01/08)
The InCl3-catalyzed sequential multicomponent reaction between 2-furfurylamine, β-dicarbonyl compounds and α,β-unsaturated aldehydes in ethanol, followed by microwave irradiation in solvent-free conditions, afforded good to excellent yields of highly substituted pyridines, with loss of a 2-furylmethyl side chain. The method was also adapted to the synthesis of quinolones, isoquinolines, phenanthridines and more complex fused pyridine systems.
Non-peptide NK1 receptor ligands based on the 4-phenylpyridine moiety
Giuliani, Germano,Cappelli, Andrea,Matarrese, Mario,Masiello, Valeria,Turolla, Elia Anna,Monterisi, Cristina,Fazio, Ferruccio,Anzini, Maurizio,Pericot Mohr, Gal.La,Riitano, Daniela,Finetti, Federica,Morbidelli, Lucia,Ziche, Marina,Giorgi, Gianluca,Vomero, Salvatore
experimental part, p. 2242 - 2251 (2011/05/06)
The quinoline nucleus of the previously described 4-phenylquinoline-3- carboxamides NK1 receptor ligands 7 has been transformed into either substituted or azole - (i.e., triazole or tetrazole) fused pyridine moieties of compounds 9 and 10, resp
6-(((SUBSTITUTED)PYRIDIN-3-YL)ALKYL)-AND ALKENYL)-TETRAHYDRO-4-HYDROXYPYRAN-2-ONE INHIBITORS OF CHOLESTEROL BIOSYNTHESIS
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, (2008/06/13)
Certain trans-6-[[(substituted)pyridin-3-yl]-alkyl-and alkenyl] tetrahydro-4-hydroxypyran-2-ones and the corresponding ring-opened acids derived therefrom are potent inhibitors of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA reducta
