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Ligand-Enabled Gold-Catalyzed C(sp2)-N Cross-Coupling Reactions of Aryl Iodides with Amines

The first example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong evidence for the in situ formation of putative high valent Au(III) intermediates.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H281NO – PubChem

 

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A practical ruthenium-catalyzed cleavage of the allyl protecting group in amides, lactams, imides, and congeners

A convenient methodology for the deprotection of N-allylic amide-like moieties was developed. The first examples accounting for the ruthenium-catalyzed deallylation of amides, lactams, imides, pyrazolidones, hydantoins, and oxazolidinones have been achieved by the sequential use of Grubbs carbene (isomerization step) and RuCl3 (oxidation step). A variety of substrates, including enantiopure multifunctional beta- and gamma-lactams, can be employed.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H283NO – PubChem

 

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Discovery of novel benzoxazinones as potent and orally active long chain fatty acid elongase 6 inhibitors

A series of benzoxazinones was synthesized and evaluated as novel long chain fatty acid elongase 6 (ELOVL6) inhibitors. Exploration of the SAR of the UHTS lead 1a led to the identification of (S)-1y that possesses a unique chiral quarternary center and a pyrazole ring as critical pharmacophore elements. Compound (S)-1y showed potent and selective inhibitory activity toward human ELOVL6 while displaying potent inhibitory activity toward both mouse ELOVL3 and 6 enzymes. Compound (S)-1y showed acceptable pharmacokinetic profiles after oral dosing in mice. Furthermore, (S)-1y significantly suppressed the elongation of target fatty acids in mouse liver at 30 mg/kg oral dosing. 2009 American Chemical Society.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H825NO – PubChem

 

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Sulfonamide-directed gold-catalyzed [2+2+2]-cycloadditions of nitriles with two discrete ynamides to construct 2,4-diaminopyridine cores

Gold-catalyzed [2+2+2]-cycloadditions of two discrete ynamides and one nitrile afford 2,4-diaminopyridine derivatives that are not readily prepared from typical low-valent-metal catalysts. Our mechanistic analysis reveals that the reaction chemoselectivity is controlled by the types of sulfonamides of ynamides.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H431NO – PubChem

 

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Design and synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines as triple reuptake inhibitors

A series of 4-bicyclic heteroaryl 1,2,3,4-tetrahydroisoquinoline inhibitors of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) was discovered. The synthesis and structure-activity relationship (SAR) of these triple reuptake inhibitors (TRIs) will be discussed. Compound 10i (AMR-2), a very potent inhibitor of SERT, NET, and DAT, showed efficacy in the rat forced-swim and mouse tail suspension models with minimum effective doses of 0.3 and 1 mg/kg (po), respectively. At efficacious doses in these assays, 10i exhibited substantial occupancy levels at the three transporters in both rat and mouse brain. The study of the metabolism of 10i revealed the formation of a significant active metabolite, compound 13.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H765NO – PubChem

 

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Copper(II)-catalysed oxidative carbonylation of aminols and amines in water: A direct access to oxazolidinones, ureas and carbamates

Copper(II) chloride catalyses the oxidative carbonylation of aminols, amine and alcohols to give 2-oxazolidinones, ureas and carbamates. Reaction proceeds smoothly in water under homogeneous conditions (Ptot = 4 MPa; PO2 = 0.6 MPa, PCO), at 100C in relatively short reaction times (4 h) and without using bases or any other additives. This methodology represents an economic and environmentally benign non-phosgene alternative for the preparation of these three important N-containing carbonyl compounds.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H406NO – PubChem

 

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Synthesis of urea derivatives from amines and CO2 in the absence of catalyst and solvent

Urea derivatives are obtained in mild to good yield from the reactions of primary aliphatic amines with CO2 in the absence of any catalysts, organic solvents or other additives. To optimize reaction conditions, experimental variables including temperature, pressure, the concentration of amine, reaction time etc. were studied. Satisfactory yields were obtained at the optimized conditions that are comparable to the presence of catalyst and solvent. The preliminary investigation of the reaction mechanism showed that alkyl ammonium alkyl carbamate was quickly formed as the intermediate, and then the final product was formed by the intramolecular dehydration.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1137NO – PubChem

 

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Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging

Provided are, among other things, compounds of formula I or IA, 1. Also provided are methods of treatment with such compounds.

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Oxazolidine – Wikipedia,
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Intramolekulare Allylsilan-Addition an chirale Alkyliden-1,3-dicarbonylverbindungen zur Synthese enantiomerenreiner trans-1,2-disubstituierter Cyclopentane und Cyclohexane

Keywords: Allylsilane; Asymmetrische Synthesen; Cyclohexane; Cyclopentane; Cyclisierungen

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Reference:
Oxazolidine – Wikipedia,
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Chemoselective debezylation of the N-1-phenylethyl group in 2-oxazolidinones by the anisole-methanesulfonic acid system

The chemoselective removal of N-1-phenylethyl group in 2-oxazolidinones by the anisole-methanesulfonic acid system was investigated. Optically active 4,5-cis- and 4,5-trans-diphenyl-2-oxazolidinones (1a-d) were easily synthesized from dl-stilbene oxides (trans- and cis-7a) using this debenzylation.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1030NO – PubChem