Archives for Chemistry Experiments of Oxazolidin-2-one

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Insecticidal activity of novel thioureas and isothioureas

BACKGROUND: We hypothesized that the exploration of chemical space around compounds with reported insecticidal activity could be a viable strategy for discovering novel, insecticidally active areas of chemistry. RESULTS: A series of thioureas and isothioureas were prepared as part of a scaffold-hopping effort around known insecticidal compounds. Many of these compounds showed excellent activity against key sap-feeding insect pests in insecticidal bioassays. While analogs bearing monocyclic thiophene head groups showed activity against Myzus persicae (green peach aphid), analogs with diarylethane head groups were active against both M. persicae and Bemisia tabaci (sweetpotato whitefly). Despite compelling activity in these laboratory tests, these compounds showed diminished activity when applied to host plants via tracksprayer. CONCLUSIONS: The initial hypothesis that structural modification of molecules reported to have insecticidal activity would yield novel compounds that also exhibit insecticidal activity was validated. Despite excellent activity in laboratory bioassays, these new compounds failed to show compelling activity in more demanding tracksprayer tests.

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Oxazolidine | C3H718NO – PubChem

 

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Mechanisms, polymerization rate scaling, and oxygen inhibition with an ultra-rapid monovinyl urethane acrylate

Certain monovinyl (meth)acrylate monomers with secondary functionalities such as urethanes have been shown to exhibit extremely rapid curing rates. In this work, the polymerization mechanism, polymerization rate scaling, and relative oxygen inhibition are evaluated for an ultra-rapid butyl urethane acrylate and an analogous aliphatic urethane diacrylate. The aliphatic urethane diacrylate was found to have increased polymerization rates at higher initiation rates relative to the butyl urethane acrylate, primarily due to different termination mechanisms. Additionally, due to higher viscosity and crosslinking density, the aliphatic urethane diacrylate was found to exhibit a greater resistance to oxygen inhibition. The flux of oxygen into the aliphatic urethane diacrylate was 1/3 that of butyl urethane acrylate. Suppressed termination likely contributes to the rapid polymerization kinetics of butyl urethane acrylate.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H455NO – PubChem

 

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Enantioselective conjugate radical addition reactions mediated by chiral Lewis acid complexes of (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4- phenyloxazoline) (DBFOX/Ph)

A high-yielding synthesis (50% overall yield) of tridentate bisoxazoline ligand (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) (DBFOX/Ph) was developed. DBFOX/Ph was subsequently tested in enantioselective conjugate radical additions onto 3-(3-phenyl-2-propenoyl)-2-oxazolidinone. Two dozen Lewis acids were evaluated, and Mg(ClO4)2 emerged as the best Lewis acid in terms of yield and enantioselectivity (100% yield, 75.4% ee (S)).

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Oxazolidine – Wikipedia,
Oxazolidine | C3H638NO – PubChem

 

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Erythromycin derivatives with antibiotic activity

Erythromycin derivatives with antibiotic activity and pharmaceutically acceptable salts thereof. A process for preparing such erythromycin derivatives and pharmaceutical compositions containing them as the active principle.

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Oxazolidine | C3H95NO – PubChem

 

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In homogeneous catalysis, the catalyst is in the same phase as the reactant. The number of collisions between reactants and catalyst is at a maximum.In a patent, 497-25-6, name is Oxazolidin-2-one, introducing its new discovery. Formula: C3H5NO2

Cu-catalyzed amidation of halogenated imidazoles

An efficient methodology involving the Cu-catalyzed amidation of halogenated imidazoles has been successfully developed. The amidated product of 5-bromo-1-alkylimidazole was further applied to the synthesis of a new chiral imidazole nucleophilic catalyst for the kinetic resolution of secondary alcohols. The Royal Society of Chemistry 2014.

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Oxazolidine | C3H1113NO – PubChem

 

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Radical aminomethylation of imines

Taking advantage of the high level of performance of N-alkoxycarbonyl-imines, we achieved the first example of addition of the aminomethyl radical to imine. The reaction efficiency depended on the structure of the radical precursor, whether it is an iodide or a xanthate, and an electron-withdrawing group on the nitrogen atom of the radical. This reaction allows direct introduction of an N-substituted aminomethyl group onto imine to provide 1,2-diamine as well as the short-step synthesis of ICI-199,441.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H534NO – PubChem

 

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INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE

The present invention is directed to compounds which inhibit farnesyl-protein transferase (FTase) and the farnesylation of the oncogene protein Ras. The invention is further directed to chemotherapeutic compositions containing the compounds of this invention and methods for inhibiting farnesyl-protein transferase and the farnesylation of the oncogene protein Ras

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Oxazolidine – Wikipedia,
Oxazolidine | C3H78NO – PubChem

 

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Recent advances in nucleophile-triggered CO2-incorporated cyclization leading to heterocycles

Carbon dioxide (CO2) has emerged as a sustainable, feasible, abundant one-carbon synthon and displays great potential in the synthesis of heterocycles such as lactones, lactams, and 2-oxazolidinones, which are privileged motifs in pharmaceutical chemistry demonstrating bioactivities. Although the fixation of CO2 is restricted due to its thermodynamic stability and kinetic inertness, multiple breakthroughs have been realized in annulation chemistry. This review concentrates on the advances made in the last five years in CO2-incorporated cyclization triggered by N-, O-, and C-nucleophiles. Three transformation modes of CO2 including carboxylative cyclization, carbonylative cyclization, and reductive cyclization have been summarized. Moreover, typical mechanisms and significant applications of these reactions are also described.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1118NO – PubChem

 

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Sequential hydroformylation/Diels-Alder processes: One-pot synthesis of polysubstituted cyclohexenes, cyclohexadienes, and phthalates from alkynes

A novel, one-pot hydroformylation/Diels-Alder sequence for the synthesis of multisubstituted cyclohexenes, cyclohexadienes, and phthalates has been developed. Various alkynes were efficiently converted into the corresponding products in good yields and with excellent diastereoselectivity through palladium-catalyzed hydroformylation followed by an AAD-type reaction (AAD: Amides-Aldehydes-Dienophiles). In view of the availability of the substrates, the atom-efficiency of the overall process, and the convenient introduction of substituents in the cyclohexene ring, this method complements current methods for the preparation of polysubstituted cyclohexane derivatives. Putting it together: A one-pot procedure for the diversity-oriented synthesis of multisubstituted cyclohexenes, cyclohexadienes, and phthalates through hydroformylation of alkynes followed by a Diels-Alder reaction has been developed (see scheme; EWG=electron-withdrawing group).

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Oxazolidine – Wikipedia,
Oxazolidine | C3H515NO – PubChem

 

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Highly stereoselective samarium(II) iodide-mediated aldol reactions of acylaziridines with aldehydes

The samarium(II) iodide-mediated stereoselective aldol reactions of acylaziridines with aldehydes are described. beta-Amino-beta?-hydroxy ketones were synthesized in high yields by the aldol reaction of aldehydes with samarium enolates generated by aziridine-fragmentation of aziridinyl ketones with two moles of samarium(II) iodide. By the choice of an appropriate nitrogen protecting group, depending on the substituent at C-3 position of aziridinyl ketone, anti,anti-beta-amino-beta?-hydroxy ketones were diastereoselectively obtained among the four possible diastereomers. Further, enantiomerically pure anti,anti-beta-amino-beta?-hydroxy ketones were successfully obtained by this aldol reaction when chiral aziridinyl ketones were used. In addition, delta-amino-?-hydroxy-beta,gamma-unsaturated esters were also synthesized in high yields by the aldol reaction of aldehydes with samarium enolates generated by aziridine-fragmentation and olefin-migration of gamma,delta-aziridinyl-alpha,beta-unsaturated esters using two moles of samarium(II) iodide. This aldol reaction proceeded with complete alpha-regioselectivity and formed (E)-olefin selectively. By introducing chiral oxazolidin-2-one auxiliary to gamma,delta-aziridinyl-alpha,beta- unsaturated carbonyl system, this reaction was extended successfully to the asymmetric reaction and enantiomerically pure syn-delta-amino-beta?- hydroxy-beta,gamma-unsaturated esters were obtained in high yields.

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Oxazolidine – Wikipedia,
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