5561-92-2Relevant articles and documents
Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones
Teske, Johannes,Plietker, Bernd
supporting information, p. 2257 - 2260 (2018/04/27)
A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.
Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones
An, Sejin,Moon, Da Yoon,Park, Bong Ser
, p. 6922 - 6928 (2018/10/24)
Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.
Acidity versus metal-induced Lewis acidity in zeolites for Friedel–Crafts acylation
Bernardon, Claire,Ben Osman, Manel,Laugel, Guillaume,Louis, Beno?t,Pale, Patrick
, p. 20 - 29 (2017/01/16)
Acid catalysts including Ni, Ag and Fe-loaded zeolites of different structures were prepared either via cationic exchange or impregnation techniques from pristine H-zeolites (BEA, and MFI). Their catalytic activity was evaluated in the liquid-phase Friedel–Crafts acylation of anisole with propanoic acid. It turned out that, whatever the doping procedure was, the zeolite loaded with transition metals led to considerable decrease in propanoic acid conversion, regardless of the nature or the metal content. However, the extent of this detrimental effect followed the order: Ag+?>?Ni2+?>?Fe3+. Pristine acidic zeolites were not only found to be the most active, but also to be the most selective toward ortho- and para-acylation products. H-ZSM-5 zeolites yielded the highest intrinsic activity, with TOF values of 0.09?h?1. The catalyst activity proved to be essentially attributed to the density and accessibility of Br?nsted acid sites, playing a key role in the activation of the reactants. Br?nsted sites are proposed to be the most likely catalytic species for performing this Friedel–Crafts acylation.
An efficient and green method for regio- and chemo-selective Friedel-Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl2]3)
Tran, Phuong Hoang,Nguyen, Hai Truong,Hansen, Poul Erik,Le, Thach Ngoc
, p. 37031 - 37038 (2016/05/24)
[CholineCl][ZnCl2]3, a deep eutectic solvent between choline chloride and ZnCl2, has been used as a dual function catalyst and green solvent for the Friedel-Crafts acylation of aromatic compounds instead of using the moisture-sensitive Lewis acids and volatile organic solvents. The reactions are performed with high yields under microwave irradiation with short reaction times for the synthesis of ketones. Interestingly, indole derivatives are regioselectively acylated in the 3-position under mild conditions with high yields without NH protection. Three new ketone products are synthesized. [CholineCl][ZnCl2]3 is easily synthesized from choline chloride and zinc chloride at a low cost, with easy purification and environmentally benign compounds. [CholineCl][ZnCl2]3 can be reused up to five times without loss of catalytic activity, making it ideal in industrial processes.
DMF as carbon source: Rh-catalyzed α-methylation of ketones
Li, Yang,Xue, Dong,Lu, Wei,Wang, Chao,Liu, Zhao-Tie,Xiao, Jianliang
supporting information, p. 66 - 69 (2014/01/23)
An unprecedented Rh-catalyzed direct methylation of ketones with N,N-dimethylformamide (DMF) is disclosed. The reaction shows a broad substrate scope, tolerating both aryl and alkyl ketones with various substituents. Mechanistic studies suggest that DMF delivers a methylene fragment followed by a hydride in the methylation process.
Advancing the mechanistic understanding of an enantioselective palladium-catalyzed alkene difunctionalization reaction
Jensen, Katrina H.,Webb, Jonathan D.,Sigman, Matthew S.
scheme or table, p. 17471 - 17482 (2011/02/27)
The mechanism of an enantioselective palladium-catalyzed alkene difunctionalization reaction has been investigated. Kinetic analysis provides evidence of turnover-limiting attack of a proposed quinone methide intermediate with MeOH and suggests that copper is involved in productive product formation, not just catalyst turnover. Through examination of substrate electronic effects, a Jaffe relationship was observed correlating rate to electronic perturbation at two positions of the substrate. Ligand effects were evaluated to provide evidence of rapid ligand exchange between palladium and copper as well as a correlation between ligand electronic nature and enantioselectivity.
PYRIDAZINONE COMPOUNDS AS CALCILYTICS
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Page/Page column 31, (2010/11/27)
Various calcilytic compounds and pharmaceutical compositions containing these compounds are disclosed. Calcilytic compounds are compounds capable of inhibiting calcium receptor activity. Methods for preparing calcilytic compounds, oral bioavailability of calcilytic compounds, and their use as calcium receptor antagonists are also disclosed.
Palladium(II)-catalyzed aerobic dialkoxylation of styrenes: A profound influence of an o-phenol
Schultz, Mitchell J.,Sigman, Matthew S.
, p. 1460 - 1461 (2007/10/03)
We report a Pd(II)-catalyzed aerobic dialkoxylation of styrene derivatives that requires an o-phenol. Initial scope and preliminary mechanistic studies are presented in which the o-phenol is proposed to facilitate the formation of a quinone methide intermediate. Copyright
Chloroindate(III) ionic liquids: Recyclable media for Friedel-Crafts acylation reactions
Earle, Martyn J.,Hakala, Ullastiina,Hardacre, Christopher,Karkkainen, Johanna,McAuley, Barry J.,Rooney, David W.,Seddon, Kenneth R.,Thompson, Julian M.,Waehaelae, Kristina
, p. 903 - 905 (2007/10/03)
Chloroindate(III) ionic liquids are versatile reaction media for Friedel-Crafts acylation reactions; the system is catalytic and totally recyclable, using an aqueous workup, with no leaching of the indium into the product phase. The Royal Society of Chemistry 2005.
COMPOUNDS, METHODS AND FORMULATIONS FOR THE ORAL DELIVERY OF A GLUCAGON LIKE PEPTIDE (GLP)-1 COMPOUND OR AN MELANOCORTIN 4 RECEPTOR (MC4) AGONIST PEPTIDE
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Page/Page column 76, (2008/06/13)
The present invention relates to novel compounds, methods, and formulations useful for the oral delivery of a GLP-1 compound or an MC4 agonist peptide.
