530-85-8Relevant articles and documents
Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed Hydroarylation and Subsequent Cadogan Cyclization
Yamamoto, Yoshishiko,Ohkubo, Erina,Shibuya, Masatoshi
, p. 1747 - 1751 (2017/05/22)
The copper-catalyzed hydroarylation of (trifluoromethyl)alkynes with (o-nitrophenyl)boronic acids selectively afforded trisubstituted (trifluoromethyl)alkenes bearing an o-nitrophenyl group. The obtained hydroarylation products were converted into 3-aryl-2-(trifluoromethyl)indoles in high yields via molybdenum-catalyzed Cadogan cyclization. Similarly, the hydroarylation product prepared from (o-nitrophenyl)(trifluoromethyl)alkyne and (p-anisyl)boronic acid also underwent Cadogan cyclization, albeit with a longer reaction time, affording the desired indole product in a high yield. (Figure presented.).
Synthesis of Piperidinone and Azepanone Fused Indoles via a Wagner-Meerwein Type 1,2-Amide Migration of 2-Spiropseudoindoxyls
Marien, Niels,Luo, Ting,Verniest, Guido
supporting information, p. 934 - 938 (2017/05/05)
Spiropseudoindoxyls were synthesized by using a gold(III)-catalyzed intramolecular nitroalkyne redox-dipolar cycloaddition cascade. These compounds were then transformed into novel piperidinone and azepanone fused indoles via a straightforward hydrogenation. The reaction mechanism of this ring expansion is believed to proceed through a rare Wagner-Meerwein type 1,2-amide migration.
Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3at room temperature
Yang, Lingling,Jiang, Linlin,Li, Yaming,Fu, Xinmei,Zhang, Rong,Jin, Kun,Duan, Chunying
, p. 3858 - 3862 (2016/07/06)
A novel Cu(I)/Ag(I)-mediated decarboxylative trifluoromethylation of arylpropiolic acids with Me3SiCF3has been developed for the construction of Csp-CF3bond under mild conditions. This method proceeds smoothly at room temperature and shows a widely functional compatibility, providing a series of corresponding trifluoromethylated acetylenyl-containing aromatics in good yields.
Synthesis of 2-spiropseudoindoxyls via an intramolecular nitroalkyne redox-dipolar cycloaddition cascade
Marien, Niels,Brigou, Ben,Pinter, Balazs,De Proft, Frank,Verniest, Guido
, p. 270 - 273 (2015/03/05)
Novel spiropseudoindoxyls were synthesized in high yields via a fully regioselective Au(III)-catalyzed cycloisomerization of easily obtainable o-nitrophenylpropiolamides, followed by an intramolecular dipolar cycloaddition as key steps. This one-pot cascade reaction resulted in new tetracyclic pseudoindoxyls, which were hydrogenated toward the title compounds as single diastereomers via N-O cleavage. The mechanism of the gold catalyzed cycloisomerization was studied by DFT and suggests a reaction path without the intermediacy of gold carbenoid species in these cases.
Discovery of novel protease activated receptors 1 antagonists with potent antithrombotic activity in vivo
Perez, Michel,Lamothe, Marie,Maraval, Catherine,Mirabel, Etienne,Loubat, Chantal,Planty, Bruno,Horn, Clemens,Michaux, Julien,Marrot, Sebastien,Letienne, Robert,Pignier, Christophe,Bocquet, Arnaud,Nadal-Wollbold, Florence,Cussac, Didier,De Vries, Luc,Le Grand, Bruno
experimental part, p. 5826 - 5836 (2010/03/24)
Protease activated receptors (PARs) or thrombin receptors constitute a class of G-protein-coupled receptors (GPCRs) implicated in the activation of many physiological mechanisms. Thus, thrombin activates many cell types such as vascular smooth muscle cells, leukocytes, endothelial cells, and platelets via activation of these receptors. In humans, thrombin-induced platelet aggregation is mediated by one subtype of these receptors, termed PAR1. This article describes the discovery of new antagonists of these receptors and more specifically two compounds: 2-[5-oxo-5-(4-pyridin-2-ylpiperazin-1-yl)penta-1,3- dienyl]benzonitrile 36 (F 16618) and 3-(2-chlorophenyl)-1-[4-(4-fluorobenzyl) piperazin-1-yl]propenone 39 (F 16357), obtained after optimization. Both compounds are able to inhibit SFLLR-induced human platelet aggregation and display antithrombotic activity in an arteriovenous shunt model in the rat after iv or oral administration. Furthermore, these compounds are devoid of bleeding side effects often observed with other types of antiplatelet drugs, which constitutes a promising advantage for this new class of antithrombotic agents. 2009 American Chemical Society.
