Elena Zaballos-Garcia

Experimental and theoretical investigations for the regio and stereoselective transformation of trans 1,2,3-trisubstituted aziridines into trans oxazolidin-2-ones

The regio and stereoselective transformation of trans 1,2,3-trisubstituted aziridines into trans oxazolidin-2-ones takes place in good yield. However, the cis configuration at C2 and C3 in monocyclic aziridines is a limiting factor for this transformation. Ab initio calculations show that while the ring-opening process assisted by iodide is regioselective, the subsequent ring-closure is responsible for the retention of the configuration at the trans oxazolidin-2-one. The larger energy found for the ring-closure process for the cis aziridines accounts for the non-formation of the cis oxazolidin-2-ones.

STEREOSELECTIVE RING TRANSFORMATION OF N-ALKYL AZIRIDINES INTO OXAZOLIDIN-2-ONES

N-Alkyl aziridines react stereoselectively with di-tert-butyl diearbonate and sodium iodide in acetone to give oxazolidin-2-ones in excellent yields.

Reaction of 3-Methylamino-1,2-diols with Dihalomethanes. Synthesis of Chiral 4-Substituted 3-Methyltetrahydro-1,3-oxazin-5-ols

Abstract Enantiomerically pure 4,5-disubstituted 3-methyltetrahydro-1,3-oxazines have been obtained by reaction of 3-methylamino-1,2-diols with dichloromethane by regioselective differentiation of hydroxyl groups.

Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo[3,2,1]oct-3-en-2-one

Abstract 2-Formylthiophene and 3-formylindole react with diethyl azodicarboxylate to give simple products derived from reactions on the formyl group whereas 2-formylfuran reacts to give the unexpected bicyclic title compound. 1 H and 13 C NMR studies indicate that this compound undergoes a series of three dynamic conformational changes over the temperature range 50 to −90°C which are ascribed to slow rotation about the exocyclic carbamate bonds and hindered bridge inversion.

Adenosine monophosphate-capped gold(I) nanoclusters: synthesis and lanthanide ion-induced enhancement of their luminescence

Reduction of Au3+ in the presence of just adenosine 5′-monophosphate (AMP) and a zwitterionic organic chemical buffering agent, specifically 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (HEPES), combined with light exposure, gives rise to luminescent, water-soluble Au+ nanoclusters (Au+ NCs). The photoluminescence of these NCs is considerably enhanced by adding Y3+ or the chemically similar Yb3+ lanthanide that leads to Au+/Y3+ and Au+/Yb3+ NCs, respectively. These NCs are characterised by absorption (steady-state), photoluminescence (steady-state and time-resolved), and X-ray photoelectron spectroscopy.

CO2 switchable nanoparticles: reversible water/organic-phase exchange of gold nanoparticles by gas bubbling

Gold nanoparticles capped with oleylamine can be effectively transferred from an organic solvent to water in the presence of an acetamidine surfactant by CO2 bubbling and then effectively reverted back to the organic phase by N2 bubbling.

Synthesis of 1,3-oxazolidines and 1,3-dioxolanes by reaction of (2R, 3R)-3-methylamino-3-phenyl-1,2-propanediol with electrophiles

Abstract The chemoselective reaction of (2R, 3R)-3-methylamino-3-phenyl-1,2-propanediol 1 with dimethoxypropane and dichloromethane under different conditions are reported as useful preparative procedures, for the synthesis 1,3-oxazolidines and 1,3-dioxolanes.

A Facile Synthesis of New 3-Substituted-2,3- dihydropyrido[3,2-d]pyrimidine-2,4-diones

Abstract Pyrido[3,2-d]pyrimidine-2,4-diones derivatives have been synthesized in good yields by two efficient synthetic routes, the first one through an hetero-cyclization on the ureas derivatives 3a–e under alkaline conditions, the second one by condensation of the isocyanate 2 with various arylalkylamines in pyridine.

Asymmetric synthesis of (−)-pseudoephedrine from (2S,3S)-3-phenyloxiran-2-ylmethanol. Stereospecific interchange of amino and alcohol functions

Abstract A ring-opening reaction of N -methylaziridines with Boc 2 O/NaI has been applied to the asymmetric synthesis of pseudoephedrine. 3-Methylamino-3-phenyl-1,2-propanediol 1 , derived from (2 S ,3 S )-3-phenyloxiran-2-ylmethanol, was converted into the oxazolidin-2-one 4 , a precursor of pseudoephedrine. The reaction occurs with a stereospecific interchange of amino and alcohol functions.

Chemoselective reactions of N1-methyl-2-hydroxy-3-methylamino-3-phenylpropanamide with electrophiles. Synthesis of chiral hexahydro-4-pyrimidinones and oxazolidines

Abstract The reactivity of (2S,3S)-N1-methyl-2-hydroxy-3-methylamino-3-phenylpropanamide 1 , containing three nucleophilic centres has been studied against dihaloalkanes and aldehydes. Hexahydro-4-pyrimidinones or oxazolidines were obtained chemoselectively. Experimental results were explained by ‘ab initio’ calculations.