17480-07-8Relevant articles and documents
Hypolipidemic activity of phthalimide derivatives. IV: Further chemical modification and investigation of the hypolipidemic activity of N-substituted imides
Chapman Jr.,Cocolas,Hall
, p. 1344 - 1347 (1983)
A further investigation of N-substituted derivatives of phthalimide for hypolipidemic activity has revealed that the chain length, as well as the type of substitution on the N-alkyl chain of phthalimide is critical for biological activity. In these studies the hypolipidemic activity was not improved by extending the chain length beyond five carbon atoms in the alkyl and alkanoic acid series. Imido nitrogen substitutents, other than alkanoic acids, methyl ketones, and alkyl groups, caused a reduction in hypolipidemic activity, e.g., hydroxy, amino, hydroxymethyl, or carbethoxy. Reduction of the keto group in the side chain to an alcohol, as well as forming derivatives of the keto group, did not improve the hypolipidemic activity with the exception of 1-N-phthalimidobutan-3-one semicarbazone. This compound demonstrated improved hypocholesterolemic activity over phthalimide and 1-N-phthalimidobutan-3-one. Substitution of the 3-position of the aromatic moiety of phthalimide with an amino or nitro group, as well as substituting a pyridine or cyclohexyl ring for the phenyl ring, led to the loss of hypolipidemic activity.
Sulfinates from Amines: A Radical Approach to Alkyl Sulfonyl Derivatives via Donor-Acceptor Activation of Pyridinium Salts
Andrews, Jonathan A.,Pantaine, Lo?c R. E.,Palmer, Christopher F.,Poole, Darren L.,Willis, Michael C.
supporting information, p. 8488 - 8493 (2021/11/01)
Synthetically versatile alkyl sulfinates can be prepared from readily available amines, using Katritzky pyridinium salt intermediates. In a catalyst-free procedure, primary, secondary, and benzylic alkyl radicals are generated by photoinduced or thermally induced single-electron transfer (SET) from an electron donor-acceptor (EDA) complex, and trapped by SO2 to generate sulfonyl radicals. Hydrogen atom transfer (HAT) from Hantzsch ester gives alkyl sulfinate products, which are used to prepare a selection of medicinal chemistry relevant sulfonyl-containing motifs.
Tuning the Selectivity of Palladium Catalysts for Hydroformylation and Semihydrogenation of Alkynes: Experimental and Mechanistic Studies
Beller, Matthias,Ge, Yao,Jackstell, Ralf,Jiao, Haijun,Liu, Jiawang,Wei, Duo,Wei, Zhihong,Yang, Ji
, p. 12167 - 12181 (2020/11/27)
Here, we describe a selective palladium catalyst system for chemodivergent functionalization of alkynes with syngas. In the presence of an advanced ligand L2 bearing 2-pyridyl substituent as a built-in base, either hydroformylation or semihydrogenation of diverse alkynes occurs with high chemo- and stereoselectivity under comparable conditions. Mechanistic studies, including density functional theory (DFT) calculations, kinetic analysis, and control experiments, revealed that the strength and concentration of acidic cocatalysts play a decisive role in controlling the chemoselectivity. DFT studies disclosed that ligand L2 not only promotes heterolytic activation of hydrogen similar to frustrated Lewis pair (FLP) systems in the hydrogenolysis step for hydroformylation but also suppresses CO coordination to promote semihydrogenation under strong acid conditions. This switchable selectivity provides a strategy to design new catalysts for desired products.
Highly chemoselective, sterically sensitive NHC-catalysed amine acylation with pyridil
Maguire, Amy C.,Kumar, Vikas,Connon, Stephen J.
supporting information, p. 13526 - 13529 (2019/11/14)
A new strategy for the protection of amines has been developed involving reaction with pyridil under the influence of N-heterocyclic carbene catalysis. The methodology is capable of distinguishing between two amines characterised by small differences in steric bulk and the resulting pyridoyl amides can be cleaved without requiring either strongly acidic or basic hydrolysis.