114772-53-1Relevant articles and documents
Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides
Walla, Peter,Kappe, C. Oliver
, p. 564 - 565 (2004)
Rapid Pd or Ni-catalyzed microwave-accelerated Negishi and Kumada cross-coupling reactions of aryl chlorides in solution and on solid phase are reported.
Design and synthesis of new tetrazolyl- and carboxy-biphenylylmethyl- quinazolin-4-one derivatives as angiotensin II AT1 receptor antagonists
Ismail, Mohamed A. H.,Barker, Stewart,Abou El Ella, Dalal A.,Abouzid, Khaled A. M.,Toubar, Rabab A.,Todd, Matthew H.
, p. 1526 - 1535 (2006)
A series of novel quinazolin-4-ones was designed and their molecular modeling simulation fitting to a new HipHop 3D pharmacophore model using CATALYST was examined. Several compounds showed significant high simulation fit values. The designed compounds were synthesized and eight of them were biologically evaluated in vitro using an AT1 receptor binding assay, where compound XX competed weakly against radiolabeled Sar1Ile 8-angiotensin II (Ang II) binding, compounds XIV and XXII showed moderate competition, and compound XXV showed almost equal ability to displace radiolabeled Sar1Ile8-Ang II binding to AT1 receptors as losartan. In vivo biological evaluation study of compounds XIV, XXII, and XXV on both normotensive and hypertensive rats revealed that compound XXV demonstrated higher hypotensive and antihypertensive activity than the reference compound losartan. To obtain a highly active compound from a candidate set of only eight tested compounds illustrates the power and utility of our pharmacophore model.
4′-Methylbiphenyl-2-carbonitrile synthesis by continuous flow Suzuki-Miyaura reaction
Estrada, Gizelda O.D.,Flores, Marcella C.,Da Silva, Joaquim F.M.,De Souza, Rodrigo O.M.A.,E Miranda, Leandro S.M.
, p. 4166 - 4168 (2012)
In the present work we report a high selective synthesis of the bicyclic core present in an important angiotensin II inhibitor family of drugs (Sartans) under continuous flow conditions. The key step in our approach was a Suzuki-Miyaura coupling using for the first time the recently described 4-toluylboronic acid MIDA ester.
A practical synthesis of 4′-methylbiphenyl-2-carbonitrile as a key intermediate of angiotensin II antagonists
Noda, Yumiki,Akiba, Yoshikazu,Kashima, Mikito
, p. 4633 - 4639 (1996)
A new and practical synthesis of 4′-methylbiphenyl-2-carbonitrile, a key intermediate of angiotensin II antagonists is described. The key step is Pd-catalyzed dehydrogenation of the compound 6, which proceeds selectively by utilizing hydrogen acceptor such as maleic diester or oxygen.
Maghemite decorated with ultra-small palladium nanoparticles (γ-Fe2O3-Pd): Applications in the Heck-Mizoroki olefination, Suzuki reaction and allylic oxidation of alkenes
Rathi, Anuj K.,Gawande, Manoj B.,Pechousek, Jiri,Tucek, Jiri,Aparicio, Claudia,Petr, Martin,Tomanec, Ondrej,Krikavova, Radka,Travnicek, Zdenek,Varma, Rajender S.,Zboril, Radek
, p. 2363 - 2373 (2016)
A nanocatalyst comprising ultra-small Pd/PdO nanoparticles (57Fe M?ssbauer spectroscopy. The cost-effective catalyst could be easily separated from the reaction mixture by using an external magnet and reused four times without any loss of activity; chemical stability and recyclability aspects of the catalyst were investigated.
Palladium nanoparticles in cross-linked polyaniline as highly efficient catalysts for Suzuki-Miyaura reactions
Fan, Haipeng,Qi, Zhengliang,Sui, Dejun,Mao, Fei,Chen, Rizhi,Huang, Jun
, p. 589 - 596 (2017)
Palladium nanoparticles supported on cross-linked polyaniline with bulky phosphorus ligands were developed. These catalysts showed high efficiency in the Suzuki-Miyaura reaction of aryl chlorides and bromides with phenylboronic acids. Aryl chlorides and bromides with functional groups, such as CN, MeO, CHO, MeCO and NO2, were converted to the corresponding biphenyls in high yields with catalyst loading. Additionally, the catalysts combined high activity with good reusability; they could be used at least five times for the Suzuki-Miyaura coupling reaction.
Highly efficient palladium catalysts supported on nitrogen contained polymers for Suzuki-Miyaura reaction
Geng, Longfei,Li, Yan,Qi, Zhengliang,Fan, Haipeng,Zhou, Zhicheng,Chen, Rizhi,Wang, Yong,Huang, Jun
, p. 24 - 28 (2016)
Through Pd catalyzed C-N coupling reaction, Pd nanoparticles and diadamantylphosphine ligand were immobilized in situ into the formed N contained polymers as heterogeneous Pd catalysts for Suzuki-Miyaura reaction. The Pd@NPad2-1.0 catalyst was found to be highly efficient and only 4 ppm of Pd (Pd@NPad2-1.0) was required for the coupling of aryl bromides with phenylboronic acid, and the corresponding products were obtained in good to excellent yields with high TON and TOF as 250,000 and 41,666 h- 1 respectively. Moreover, the coupling of various aryl chlorides with phenylboronic acids gave the corresponding products in high yields also. And the Pd@NPad2-1.0 catalyst is reusable at least 5 times with only slight deactivation.
Cross-coupling of chloroarenes with boronic acids using a water-soluble nickel catalyst
Galland, Jean-Christophe,Savignac, Monique,Genet, Jean-Pierre
, p. 2323 - 2326 (1999)
Various biarylic compounds are prepared by cross-coupling reactions between arylboronic acids and aromatic chlorides in organoaqueous medium. These reactions are performed using an hydrosoluble Ni(0) catalyst preformed from NiCl2(dppe) and TPPTS.
Benzyloxycalix[8]arene: A new valuable support for NHC palladium complexes in C-C Suzuki-Miyaura couplings
Abdellah, Ibrahim,Kasongo, Pauline,Labattut, Axel,Guillot, Régis,Schulz, Emmanuelle,Martini, Cyril,Huc, Vincent
, p. 13843 - 13848 (2018)
Benzyloxycalix[8]arene supported catalysts bearing N-heterocyclic carbene palladium complexes on each subunit were readily synthesized. Intermediates and catalysts were fully characterized, allowing for a fine control of their structure. X-ray diffraction analysis confirmed the formation of a calix[8]arene bearing eight well-defined NHC palladium complexes. The macrocyclic structure of calix[8]arenes allowed for a scalable and chromatography-free catalyst synthesis under homogeneous conditions, while the catalytic reaction proceeded under heterogeneous conditions, just by changing the nature of the solvent. Indeed, when used as a suspension in ethanol, a high TON and TOF were obtained through a large panel of functionalized brominated substrates in C-C Suzuki-Miyaura couplings, with low metal contamination after simple filtration.
An efficient and green synthetic route to losartan
Shuangxia, Feng,Zheng, Gu,Yelv, Tang,Hui, Liu,Guofang, Jiang
, p. 451 - 454 (2015)
A practical, efficient and green process for the preparation of losartan, an antihypertensive drug, has been developed with an overall yield of 58.6%. The key step is the synthesis of the two key intermediates 2-butyl-4-chloro-3H-imidazole-5-carbaldehyde (BCFI) and 2-cyano-4'-methyl biphenyl (OTBN). BCFI was synthesised from valeronitrile and acetyl chloride by three steps with an overall yield of 69%; OTBN was obtained in 86% yield by the coupling of o-chlorobenzonitrile with p-methylphenylmagnesium chloride in tetrahydrofuran in the presence of manganese chloride and chlorotrimethylsilane. The above route was successfully operated in at a pilot-plant operation.
