- Phosphoramidates: Features of the formation mechanism and the relationship structure-bioaction
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Mechanism of the synthesis of phosphoramidates by Todd-Atherton reaction is based on the primary interaction of a polyhaloalkane with the highly basic amine to form a 1:1 associate. The subsequent attack by the associate on the hydrophosphoryl compound of "symmetric" structure leads to the formation of the target compounds in high yields. The test of the effect of dialkyl hexamethylene- and dialkyl(pyridin-2-yl)-phosphoramidates in vitro against the strains of a number of the producents of pathogenic bacteria and mycotoxins showed that the high level of biological activity of the target compounds is correlated well with the physicochemical parameters characterizing their structure.
- Krutikov,Erkin,Krutikova
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- Practical and regioselective amination of arenes using alkyl amines
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The formation of carbon–nitrogen bonds for the preparation of aromatic amines is among the top five reactions carried out globally for the production of high-value materials, ranging from from bulk chemicals to pharmaceuticals and polymers. As a result of this ubiquity and diversity, methods for their preparation impact the full spectrum of chemical syntheses in academia and industry. In general, these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C–H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process enables the easy preparation of advanced building blocks, tolerates a broad range of functionalities, and multigram scale can be achieved via a batch-to-flow protocol. The merit of this strategy as a late-stage functionalization platform has been demonstrated by the modification of several drugs, agrochemicals, peptides, chiral catalysts, polymers and organometallic complexes.
- Ruffoni, Alessandro,Juliá, Fabio,Svejstrup, Thomas D.,McMillan, Alastair J.,Douglas, James J.,Leonori, Daniele
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p. 426 - 433
(2019/05/01)
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- 3-Hydroxy-1,5-dihydro-2H-pyrrol-2-ones as novel antibacterial scaffolds against methicillin-resistant Staphylococcus aureus
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Herein, we report the synthesis and evaluation of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones as antibacterial agents against methicillin-resistant S. aureus (MRSA) and methicillin-resistant S. epidermidis (MRSE). Lead compound 38 showed minimum inhibitory concentrations (MICs) of 8 and 4 μg/mL against MRSA and MRSE, respectively. Furthermore, compound 38 displayed a MIC of 8–16 μg/mL against linezolid-resistant MRSA. These molecules, previously underexplored as antibacterial agents, serve as a new scaffold for antimicrobial development.
- Cusumano, Alexander Q.,Pierce, Joshua G.
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supporting information
p. 2732 - 2735
(2018/03/12)
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- Copper-catalyzed amination of silyl ketene acetals with N-chloroamines
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A copper(I)/2,2′-bipyridyl complex catalyzes an amination reaction of silyl ketene acetals with N-chloroamines, presenting a new preparative method of α-amino esters.
- Miura, Tomoya,Morimoto, Masao,Murakami, Masahiro
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supporting information
p. 5214 - 5217,4
(2020/09/02)
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- Gasphase Reactions, 61. - Cycloalkanimines 2H-Azirine, 1-Azetidine, 1-Pyrroline, 1-Piperideine, and 3,4,5,6-Tetrahydro-2H-azepine: Preparation and Photoelectron Spectra
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For preparation of the easily oligomerizing cycloalkanimines , the following gasphase reactions are optimized PE spectroscopically: for the three membered ring imine, 2H-azirine, the heterogeneous KOR dehydrochlorination of the 2-chloroethyl azide preceding the thermolysis of the resulting vinyl azide, and for the lager rings, 1-azetine (n=2), 1-pyrroline (n=3), 1-piperideine (n=4) as well as the seven-membered 3,4,5,6-tetrahydro-2H-azepine, the consecutive chlorination of the corresponding cycloalkylamine over solid N-chlorosuccinimide followed by KOR dehydrochlorination of the N-chloro derivative formed.The PE spectra of all cyclic alkanimines prepared are assigned based on geometry-optimized MNDO calculations, and their electronic structures are discussed by molecular state comparison with increasing ring size and with the isoelectronic series of the cycloalkenes.The thermal ring opening of 1-azetine to 2-azabutadiene is investigated by PE spectroscopic real-time gas analysis; its ionization pattern is assigned by comparison with other azabutadienes.
- Bock, Hans,Dammel, Ralph
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p. 1971 - 1986
(2007/10/02)
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