10017-39-7Relevant academic research and scientific papers
An efficient synthesis of 2-(((9- fluorenylmethoxycarbonyl)amino)methyl)benzoic acid
Sun, Jung-Hui,Daneker, Wayne F.
, p. 4525 - 4530 (1998)
An efficient, two-step synthesis of the title compound 3 in 61% overall yield is presented. The synthesis involves hydrazine removal of the N- phthalimide protecting group of α-phthalimido-o-toluic acid (6), followed by N-Fmoc formation with (9-fluorenylm
Merging C-H Activation and Strain-Release in Ruthenium-Catalyzed Isoindolinone Synthesis
Hu, Xiao-Qiang,Liu, Zi-Kui,Hou, Ye-Xing,Xu, Ji-Hang,Gao, Yang
, p. 6332 - 6336 (2021)
The merger of strain-release of 1,2-oxazetidines with carboxylic acid directed C-H activation in catalytic synthesis of isoindolinones is reported for the first time. This reaction opens a new and sustainable avenue to prepare a range of structurally dive
Attachment of a hydrogen-bonding carboxylate side chain to an [FeFe]- hydrogenase model complex: Influence on the catalytic mechanism
Gao, Weiming,Sun, Junliang,Akermark, Torbjoern,Li, Mingrun,Eriksson, Lars,Sun, Licheng,Akermark, Bjoern
, p. 2537 - 2546 (2010)
Azapropanedithiolate (adt)- bridged model complexes of [FeFe]-hydrogenase bearing a carboxylic acid functionality have been designed with the aim of decreasing the potential for reduction of protons to hydrogen. Protonation of the bisphosphine complexes 4-6 has been studied by in situ IR and NMR spectroscopy, which revealed that protonation with triflic acid most likely takes place first at the N-bridge for complex 4 but at the Fe-Fe bondfor complexes 5 and 6. Using an excess of acid, the diprotonated species could also be observed, but none of the protonated species was sufficiently stable to be isolated in a pure state. Electrochemical studies have provided an insight into the catalytic mechanismsunder strongly acidic conditions, and have also shown that complexes 3 and 6 are electro-active in aqueous solution even in the absence of acid, presumably due to hydrogen bonding. Hydrogen evolution, driven by visible light, has been observed for three-component systems consisting of [Ru(bpy)3]2+ ,complex 1, 2, or 3, and ascorbic acid in CH3CN/D2O solution by on-line mass spectrometry.
Electrochemical-induced benzyl C-H amination towards the synthesis of isoindolinones via aroyloxy radical-mediated C-H activation
Gao, Yuhan,Huang, Zhiliang,Lei, Aiwen,Yi, Hong,Yu, Mingming,Zhang, Lin,Zhang, Yingjie,Zhang, Yiyan
, p. 1445 - 1450 (2022/03/08)
The rapid synthesis of valuable isoindolinones with cheap and easily available starting materials under mild conditions is of great importance, but is challenging. We enclose here a novel electrochemical strategy to selectively and sustainably access isoindolinone using simple o-alkyl benzoic acids and nitriles as substrates under metal catalyst and external oxidant-free conditions. The protocol shows a very good functional group tolerance. Mechanistic investigations suggest that aroyloxy radicals are involved in this transformation, which initiates the benzylic C-H amination event by a 1,5-HAT process. Meanwhile, nitrile as the nitrogen source plays a vital role, as its derived intermediate facilitates the construction of the amide bond in the product.
Cu/Fe Catalyzed Intermolecular Oxidative Amination of Benzylic C-H Bonds
Liu, Cong,Zhang, Qi,Li, Hongbo,Guo, Shuangxi,Xiao, Bin,Deng, Wei,Liu, Lei,He, Wei
supporting information, p. 6208 - 6212 (2016/05/09)
We report a Cu/Fe co-catalyzed Ritter-type C-H activation/amination reaction that allows efficient and selective intermolecular functionalization of benzylic C-H bonds. This new reaction is featured by simple reaction conditions, readily available reagents and general substrate scope, allowing facile synthesis of biologically interesting nitrogen containing heterocycles. The Cu and Fe salts were found to play distinct roles in this cooperative catalysis. With a little help: A Ritter-type intermolecular amination of benzylic C-H bonds with acetonitrile, co-catalyzed by CuII/FeIII is reported. A wide array of biologically interesting nitrogen containing heterocycles was prepared from 2-alkyl benzoic acids and heteroaromatic carboxylic acids under operationally simple conditions. The Cu and Fe salts were found to play distinct roles in this cooperative catalysis.
Synthesis and evaluation of novel aromatic substrates and competitive inhibitors of GABA aminotransferase
Clift, Michael D.,Silverman, Richard B.
, p. 3122 - 3125 (2008/12/22)
The design, synthesis, and evaluation of novel γ-aminobutyric acid aminotransferase (GABA-AT) inhibitors and inactivators can lead to the discovery of new GABA-related therapeutics. To this end, a series of aromatic amino acid compounds was synthesized to aid in the design of new inhibitors and inactivators of GABA-AT. All compounds were tested as competitive inhibitors of GABA-AT. The amino acids with benzylic amines were also tested as substrates for GABA-AT. It was found that these compounds were all poor competitive inhibitors of GABA-AT, but some were substrates of the enzyme, suggesting their utility as scaffolds for potential GABA-AT mechanism-based inactivators. Computer modeling was used to rationalize the substrate activity of the various compounds.
