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The Evans Aldol-Prins cyclization: A general and stereoselective method for the synthesis of 2,3,4,5,6-pentasubstituted tetrahydropyrans

A general and stereoselective method to synthesize 2,3,4,5,6-pentasubstituted tetrahydropyrans in three steps starting from three different aldehydes is described. Key substrates beta,gamma-unsaturated N-acyloxazolidin-2-ones were subjected to an “Evans Aldol-Prins” protocol to generate five sigma-bonds and five stereocenters in only a one-pot process with yields up to 60% and excellent stereoselectivities.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H296NO – PubChem

 

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NMR study on the oxidative degradation of MEA in presence of Fe 2+

Qualitative and quantitative NMR experiments were performed on 5M aqueous solutions of monoethanolamine (MEA) loaded with CO2 (alpha = 0.4) and in presence of 1mM FeSO4 x 7H2O as a catalyst. The main degradation products were identified and quantified by 1D and 2D NMR Spectroscopy as: N-(2-hydroxyethyl) imidazole (HEI), 2-oxazolidone (OZD), N-(2-hydroxyethyl) formamide (HEF). There are also some other signals not quantified yet because of the low intensity. The NMR results were compared with GC/LC-MS results of the same solution.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H445NO – PubChem

 

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Cyclic sulphenamide compounds, their production and their medicinal use

The invention relates to cyclic sulphenamides of Formula I and methods for their manufacture. Also included in the invention are compositions containing said cyclic sulphenamides and methods for the use of said compounds and compositions as lipoxygenase inhibitors.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H41NO – PubChem

 

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Complementary synthetic approaches to constitutionally diverse N-aminoalkylated isoindolinones: Application to the synthesis of falipamil and 5-HT1A receptor ligand analogues

Different synthetic approaches for the elaboration of poly and diversely substituted isoindolinones tailed with constitutionally diverse aminoalkylated chains have been developed. The key step is based upon the preliminary assembly of the isoindolinone template equipped with hydroxyalkyl appendages. Subsequent manipulation of the terminal hydroxy functionality afforded the targeted compounds and the synthetic utility of these approaches has been emphasized by the synthesis of the bradycardic agent falipamil and 5-HT1A receptor ligand analogues. Georg Thieme Verlag Stuttgart.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H772NO – PubChem

 

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The dihydrofuran template approach to furofuran synthesis

Flash vacuum pyrrolysis of vinyl epoxides provides cis-dihydrofuran carboxylic esters in good yields and diastereoselectivities, which, on base-promoted epimerisation afford the complementary trans series. The compounds provide a viable template for a Lewis acid promoted cyclisation to provide the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane core found in the furofuran series of natural lignans. This strategy is stereodivergent and can be controlled to provide the exo-exo, exo-endo or endo-endo stereochemistries. The approach has been exemplified in syntheses of the sesamyl furofurans (¡À)-epiasarinin and (¡À)-asarinin. The Royal Society of Chemistry 2006.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H285NO – PubChem

 

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Palladium-catalyzed hydroacyloxylation of ynamides

In the presence of substoichiometric Pd(OAc)2, carboxylic acids undergo highly regio- and stereoselective additions to ynamides to provide alpha-acyloxyenamides.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1010NO – PubChem

 

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TERAHYDROBENZAZEPINES AS ANTAGONISTS AND/OR REVERSE AGONISTS OF THE HISTAMINE H3 RECEPTOR

The present invention relates to novel benzazepine derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurological and psychiatric disorders.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H194NO – PubChem

 

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Synthesis of Nitrogen-Containing Goniothalamin Analogues with Higher Cytotoxic Activity and Selectivity against Cancer Cells

Two series of racemic goniothalamin analogues displaying nitrogen-containing groups were designed and synthesized. A total of 19 novel analogues were evaluated against a panel of four different cancer cell lines, along with the normal prostate cell line PNT2 to determine their selectivity. Among them, goniothalamin chloroacrylamide 13 e displayed the lowest IC50 values for both MCF-7 (0.5 mum) and PC3 (0.3 mum) cells, about 26-fold more potent than goniothalamin (1). Besides its higher potency, compound 13 e also displayed much higher selectivity than goniothalamin. In contrast, goniothalamin isobutyramide 13 c was the most potent analogue against Caco-2 cells (IC50=0.8 mum), about 10-fold more potent and 17-fold more selective than 1. These results reveal the potential of compounds 13 c and 13 e for further in vivo studies, representing the first goniothalamin analogues with IC50 values in the low micromolar range and high selectivity against MCF-7, Caco-2, and PC3 cancer cell lines.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H808NO – PubChem

 

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Phosphazene/triisobutylaluminum-promoted anionic ring-opening polymerization of 1,2-epoxybutane initiated by secondary carbamates

Attempts to use a carbamate-phosphazene base as the initiating system for the polymerization of 1,2-epoxybutane was unsuccessful. As a matter of fact, carbamate deprotonation by phosphazene bases led to their fast decomposition generating alkoxide anions which initiate the polymerization rather than carbamate anions. Conversely, in the presence of triisobutylaluminum-a Lewis acid-the in situ generation of an anionic initiator X- obtained by the deprotonation of the tBuP4 phosphazene base was tested as a possible way to initiate the polymerization of 1,2-epoxybutane. Particular attention was given to the detection of eventual transfer or side-reactions according to the carbamate:triisobutylaluminum:phosphazene base ratio, to the solvent dielectric constant and to the number of PN- units in the phosphazene base. The reaction was performed with a stoichiometric ratio (1::1:1) of carbamate:triisobutylaluminum:tBuP2, which gave the best results. Under these conditions, the initiation of the polymerization by the carbamate anion was quantitative; no transfer reactions have been observed and the polymerization proceeded in a controlled manner to afford amide end-capped poly(butylene oxide) with a narrow molar mass distribution and expected molar masses.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H597NO – PubChem

 

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In vitro antitumor evaluation of some new tetra substituted 1,2,4-triazines

A new series of tetra substituted 1,2,4-triazines (4, 5, 7 and 8) was synthesized via the reaction of 3,1-oxazolinone (1) with thiosemicarbazide to give 6-hydroxy-5-(p-hydroxybenzylidene)-3-phenyl-2-(amino) thioxo-1,2,4-triazine (3). Treatment of 1,2,4-triazine derivative 3 with carbon disulphide and p-chlorophenacyl bromide yielded the corresponding 1,2,4-triazine derivatives 4 and 7. Acetylation of tetra-substituted 1,2,4-tri-azines 4 and 7 with acetic anhydride gave tri acetyl and di acetyl derivatives 5 and 8. Compounds structure was confirmed by IR,1H,13C-NMR, MS, and elemental analysis. The cytotoxic activities of some synthesized, 1,2,4-triazines were evaluated on human hepatocellular carcinoma cells (HepG-2) and human colon carcinoma cells (HCT-116) using the MTT method. We found that, compounds 5 (IC50 = 3.60 mug/mL) and 8 (IC50 = 4.40 mug/mL) have better activity against HCT-116 cell line than the reference doxorubcin (IC50 = 5.30 mug/mL), while compound 7 has best activity against HepG-2 cell line.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H286NO – PubChem