193964-34-0Relevant academic research and scientific papers
Cu/Fe/O=PPh3-catalyzed etherification for the synthesis of aryl 3-benzo[b]thienyl ethers
Mitsudo, Koichi,Asada, Takuya,Inada, Tomohiro,Kurimoto, Yuji,Mandai, Hiroki,Suga, Seiji
supporting information, p. 1044 - 1047 (2018/08/24)
Cu/Fe-cocatalyzed cross-coupling reactions between 3-bromobenzo[b]thiophene and hydroxyaryls are described herein. The combination of Cu and Fe catalysts is important for the progress of the reactions, and the use of triphenylphosphine oxide as a ligand suppresses the dehalogenation of 3-bromobenzo[b]thiophene, and promptly facilitates the reaction. The obtained aryl benzo[b]thienyl ethers can be converted to π-extended thienobenzofuran derivatives via Pd-catalyzed dehy-drogenative cyclizations.
Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings
Zhai, Yuntong,Chen, Xiaofei,Zhou, Wei,Fan, Mengyang,Lai, Yisheng,Ma, Dawei
, p. 4964 - 4969 (2017/05/12)
Diaryl formation is achieved by coupling phenols and (hetero)aryl halides under the catalysis of CuI/N,N′-bis(2-phenylphenyl) oxalamide (BPPO) or CuI/N-(2-phenylphenyl)-N′-benzyl oxalamide (PPBO) at 90 °C using DMF or MeCN as the solvent. Only 0.2-2 mol % CuI and ligand are required for complete conversion, which represents the lowest catalytic loadings for a general Cu/ligand-catalyzed diaryl ether formation.
A new biarylphosphine ligand for the Pd-catalyzed synthesis of diaryl ethers under mild conditions
Salvi, Luca,Davis, Nicole R.,Ali, Siraj Z.,Buchwald, Stephen L.
supporting information; experimental part, p. 170 - 173 (2012/03/08)
A new bulky biarylphosphine ligand (L8) has been developed that allows the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols under milder conditions than previously possible. A direct correlation between the size of the ligand substituents in the 2′, 4′, and 6′ positions of the nonphosphine containing ring and the reactivity of the derived catalyst system was observed. Specifically, the rate of coupling increased with the size of these substituents.
Efficient access to 2-aryl-3-substituted benzo[b]thiophenes
David, Emilie,Perrin, Julie,Pellet-Rostaing, Stephane,Fournier Dit Chabert, Jeremie,Lemaire, Marc
, p. 3569 - 3573 (2007/10/03)
(Chemical Equation Presented) Benzo[b]thiophene derivatives are important in part because of their use as selective estrogen receptor modulators. They are usually synthesized by intramolecular cyclization. Here, we propose a method for the synthesis of 2-
Diamino benzo[b]thiophene derivatives as a novel class of active site directed thrombin inhibitors. 5. Potency, efficacy, and pharmacokinetic properties of modified C-3 side chain derivatives
Sall, Daniel J.,Bailey, Dianna L.,Bastian, Jolie A.,Buben, John A.,Chirgadze, Nickolay Y.,Clemens-Smith, Amy C.,Denney, Michael L.,Fisher, Matthew J.,Giera, Deborah D.,Gifford-Moore, Donetta S.,Harper, Richard W.,Johnson, Lea M.,Klimkowski, Valentine J.,Kohn, Todd J.,Lin, Ho-Shen,McCowan, Jefferson R.,Palkowitz, Alan D.,Richett, Michael E.,Smith, Gerald F.,Snyder, David W.,Takeuchi, Kumiko,Toth, John E.,Zhang, Minsheng
, p. 649 - 663 (2007/10/03)
A systematic investigation of the structure-activity relationships of the C-3 side chain of the screening hit la led to the identification of the potent thrombin inhibitors 23c, 28c, and 31c. Their activities (1240, 903, and 1271 x 106 L/mol, respectively) represent 2200- and 2900-fold increases in potency over the starting lead la. This activity enhancement was accomplished with an increase of thrombin selectivity. The in vitro anticoagulant profiles of derivatives 28c and 31c were determined, and they compare favorably with the clinical agent H-R-1-[4aS,- 8aS]perhydroisoquinolyl-prolyl-arginyl aldehyde (D-Piq-Pro-Arg-H; 32). The more potent members of this series have been studied in an arterial/venous shunt (AV shunt) model of thrombosis and were found to be efficacious in reducing clot formation. However, their efficacy is currently limited by their rapid and extensive distribution following administration.
