844656-92-4Relevant academic research and scientific papers
Potentiation of the fosmidomycin analogue FR 900098 with substituted 2-oxazolines against Francisella novicida
Stephens, Matthew D.,Yodsanit, Nisakorn,Melander, Christian
supporting information, p. 1952 - 1956 (2016/10/22)
A library of 33 compounds was screened for potentiation of the antibiotic FR 900098 against the Francisella tularensis surrogate Francisella novicida. From the screen a highly potent 2-oxazoline adjuvant was discovered capable of potentiating FR 900098 with a 1000-fold reduction in MIC against the Francisella sub-species F. novicida and F. philomiragia.
METHOD OF REGIOSELECTIVE SYNTHESIS OF SUBSTITUTED BENZOATES
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Page/Page column 11; 18; 19, (2013/03/26)
A method of synthesis of para-substituted benzoate esters and acids is provided, wherein the para-substituted regioisomer is obtained substantially free of the meta-substituted impurity, the method comprising contacting a coumalate ester or acid and an un activated alkene at elevated temperature in the presence of a metal oxidation catalyst and an oxidant. The metal oxidation catalyst can be palladium, such as palladium on carbon, and the oxidant can be the oxygen gas in ambient air. The reaction can be carlied out without solvent or in high boiling hydrocarbon solvents such as mesitylene. When the un activated alkene is a monosubstituted alkene, yields of at least about 50 or 60% of para-substituted ester and acid products, respectively, are obtained, substantially free of the regioisomelic meta-substituted impurity.
Aromatics from pyrones: Para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate
Kraus, George A.,Riley, Sean,Cordes, Travis
experimental part, p. 2734 - 2736 (2011/11/06)
The Diels-Alder reaction of coumalic acid and methyl coumalate with unactivated alkenes provides only para-substituted adducts in good yield.
Preparation, structure, and reactivity of nonstabilized organoiron compounds. Implications for iron-catalyzed cross coupling reactions
Fuerstner, Alois,Martin, Ruben,Krause, Helga,Seidel, Guenter,Goddard, Richard,Lehmann, Christian W.
, p. 8773 - 8787 (2008/12/23)
A series of unprecedented organoiron complexes of the formal oxidation states -2, 0, +1, +2, and +3 is presented, which are largely devoid of stabilizing ligands and, in part, also electronically unsaturated (14-, 16-, 17- and 18-electron counts). Specifically, it is shown that nucleophiles unable to undergo β-hydride elimination, such as MeLi, PhLi, or PhMgBr, rapidly reduce Fe(3+) to Fe(2+) and then exhaustively alkylate the metal center. The resulting homoleptic organoferrate complexes [(Me4Fe)(MeLi)] [Li(OEt2)]2 (3) and [Ph4Fe][Li(Et 2O)2][Li(1,4-dioxane)] (5) could be characterized by X-ray crystal structure analysis. However, these exceptionally sensitive compounds turned out to be only moderately nucleophilic, transferring their organic ligands to activated electrophiles only, while being unable to alkylate (hetero)aryl halides unless they are very electron deficient. In striking contrast, Grignard reagents bearing alkyl residues amenable to β-hydride elimination reduce FeXn (n = 2, 3) to clusters of the formal composition [Fe(MgX)2]n. The behavior of these intermetallic species can be emulated by structurally well-defined lithium ferrate complexes of the type [Fe(C2H4) 4][Li(tmeda)]2 (8), [Fe(cod)2][Li(dme)] 2 (9), [CpFe(C2H4)2][Li(tmeda)] (7), [CpFe(cod)][Li(dme)] (11), or [Cp*Fe(C2H4) 2][Li(tmeda)] (14). Such electron-rich complexes, which are distinguished by short intermetallic Fe-Li bonds, were shown to react with aryl chlorides and allyl halides; the structures and reactivity patterns of the resulting organoiron compounds provide first insights into the elementary steps of low valent iron-catalyzed cross coupling reactions of aryl, alkyl, allyl, benzyl, and propargyl halides with organomagnesium reagents. However, the acquired data suggest that such C-C bond formations can occur, a priori, along different catalytic cycles shuttling between metal centers of the formal oxidation states Fe(+1)/Fe(+3), Fe(0)/Fe(+2), and Fe(-2)/Fe(0). Since these different manifolds are likely interconnected, an unambiguous decision as to which redox cycle dominates in solution remains difficult, even though iron complexes of the lowest accessible formal oxidation states promote the reactions most effectively.
