676272-24-5Relevant academic research and scientific papers
Direct Cyclopropanation of α-Cyano β-Aryl Alkanes by Light-Mediated Single Electron Transfer Between Donor–Acceptor Pairs
Li, Jing,Lear, Martin J.,Hayashi, Yujiro
supporting information, p. 5901 - 5905 (2021/03/09)
Cyclopropanes are traditionally prepared by the formal [2+1] addition of carbene or radical based C1 units to alkenes. In contrast, the one-pot intermolecular cyclopropanation of alkanes by redox active C1 units has remained unrealised. Herein, we achieve
Reductive alkylation of active methylene compounds with carbonyl derivatives, calcium hydride and a heterogeneous catalyst
Guyon, Carole,Duclos, Marie-Christine,Sutter, Marc,Métay, Estelle,Lemaire, Marc
supporting information, p. 7067 - 7075 (2015/06/25)
A one-pot two-step reaction (Knoevenagel condensation - reduction of the double bond) has been developed using calcium hydride as a reductant in the presence of a supported noble metal catalyst. The reaction between carbonyl compounds and active methylene
Atom- and step-economical preparation of reduced knoevenagel adducts using CO as a deoxygenative agent
Kolesnikov, Pavel N.,Usanov, Dmitry L.,Barablina, Evgeniya A.,Maleev, Victor I.,Chusov, Denis
supporting information, p. 5068 - 5071 (2014/12/11)
A highly efficient one-step Rh-catalyzed preparation of reduced Knoevenagel adducts of various aldehydes and ketones with active methylene compounds has been developed. The protocol does not require an external hydrogen source and employs carbon monoxide
Synthesis of cationic antimicrobial β2′2-amino acid derivatives with potential for oral administration
Hansen, Terkel,Ausbacher, Dominik,Flaten, Goril E.,Havelkova, Martina,Str?m, Morten B.
supporting information; experimental part, p. 858 - 868 (2011/04/18)
We have prepared a series of highly potent achiral cationic β 2, 2-amino acid derivatives that fulfill the Lipinski's rule of five and that contain the basic structural requirements of short cationic antimicrobial peptides. Highest antimicrobial potency was observed for one of the smallest β2, 2-amino acid derivatives (Mw 423.6exhibiting a MIC of 3.8 μM against methicillin-resistant Staphylococcus aureus (MRSA), methicillin-resistant Staphylococcus epidermidis (MRSE), and Staphylococcus aureus, and 7.7 μM against Escherichia coli. The β 2, 2-amino acid derivatives were shown to have similar absorption properties as several commercially available drugs, and the results implied a resembling membrane disrupting mechanism of action as reported for much larger cationic antimicrobial peptides. By their high potency, nontoxicity, absorption properties, and ease of synthesis, the β2, 2-amino acid derivatives demonstrate a way to modify a vastly investigated class of cationic antimicrobial peptides into small druglike molecules with high commercial potential.
Superacid-catalyzed intramolecular cyclization reaction of arylcyanopropionate: Geminal substitution effect on superelectrophilicity
Nakamura, Satoshi,Sugimoto, Hiromichi,Ohwada, Tomohiko
, p. 4219 - 4224 (2008/09/20)
(Chemical Equation Presented) We present superacid-catalyzed intramolecular cyclization reactions of arylcyanopropionates to give cyclized five- and six-membered β-enamino esters in moderate to high yields. Known intramolecular ring-closing reactions of protonated nitrile to aromatic carbon atom are limited to the 6-membered case. Interestingly, a significant synergistic increase of reactivity of the cyano functionality was observed, and the cyano nitrogen atom was converted into an amino group, when an ester group was present in a geminal arrangement. Deuterium exchange experiments excluded the involvement of deprotonation of the α-proton in the cyclization process. The acidity dependence of the cyclization reactions and 13C NMR studies of a model compound, methyl cyanoacetate, in various acidic media were consistent with the involvement of the O,N-diprotonated dication of methyl cyanoacetate, a distonic dication, in strong acid, and this is considered to be the de facto electrophile in the present cyclization reaction of arylcyanopropionates.
