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1,8-DIAZABICYCLO<5.4.0>UNDEC-7-ENE(DBU): AN EFFECTIVE BASE FOR THE INTRODUCTION OF t-BUTYLDIMETHYLSILYL GROUP IN ORGANIC COMPOUNDS.

Reaction of alcohols, thiols, amines, carboxylic acids, phenols, hydroquinones, ketoesters and amides with equimolecular amounts of t-butyldimethylchlorosilane and DBU, even in solvents other than dimethylformamide affords the corresponding t-butyldimethylsilyl derivatives in high yield.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H277NO – PubChem

 

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The role of oxazolidine derivatives in the treatment of infectious and chronic diseases

Background: Despite being known for their antibacterial activity, the oxazolidines are molecules with wide pharmacological action and may act as anticonvulsants, anti-inflammatory and antineoplasic agents. However, such activities have been poorly explored and only two oxazolidinic derivatives hit the market until now. Therefore, this review covers the main biological activities of oxazolidines, indicating which of the classes and substituents have the best biological results as well as the synthesis methodology used to obtain them. Methods: The search for bibliographic data was made using a question focused on the oxazolidine structure and their respective activities, besides using inclusion/exclusion criteria clearly defined. The selected papers were subjected to qualitative content analysis methodology to be used in this review. Results: The oxazolidines remain excellent candidates for antibacterial, presenting three compounds in clinical testing phase (Radezolide, Cadezolide and Sutezolide), besides being a good candidate as antitubercular agents. Other less explored activities have niches with a great therapeutic potential such as the oxazolidines acting on 5-HT receptors (anticonvulsant) and Zolmitriptan (anti-migraine), and also mefloquine-oxazolidine derivatives which may act as antineoplasic and antitubercular agents. Conclusion: This review summarizes the versatility and great therapeutic potential that oxazolidines can offer, reinforcing the need for further studies and investments for this class of molecules.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H366NO – PubChem

 

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Follow-on drugs: How far should chemists look?

A major remark made by observers relates to the focus of the pharmaceutical industry on ‘me-too’ drugs rather than ‘first-in-class’ drugs, the latter are considered to be ‘truly’ innovative medicines. Although the subject is heavily debated, chemists in project teams around the globe are routinely following up compounds from competitors. An important strategic consideration is the degree of chemical modification of the original structure required for success. Here, we present an analysis of the DiMasi and Faden set of first-in-class and follow-on drug pairs (n = 74); showing that 70% of them are structurally very similar, meaning that they are characterized by minimal structural variations. This highlights the fact that even simple atomic variations can cause drastic changes in molecular properties responsible for therapeutic advantages.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H557NO – PubChem

 

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Total Synthesis of Al-77-B

Stereoselective hydroxylation of the beta-lactam ester 8 is a key step in a total synthesis of Al-77-B 1.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H375NO – PubChem

 

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Observations on the direct amidocyclopropanation of alkenes using organozinc carbenoids

A series of amidocyclopropanes were prepared by direct amidocyclopropanation of alkenes, using organozinc carbenoids generated from readily available diethoxymethylamides. The amidocyclopropanation of monosubstituted alkenes led to selective formation of the trans-amidocyclopropane in most cases, but with more substituted alkenes, the stereochemical outcome of the cyclopropanation reactions was unpredictable. The amidocyclopropane products can be readily elaborated to structurally interesting cyclopropane containing amino acids or amino alcohols.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H842NO – PubChem

 

The Absolute Best Science Experiment for Isoxazolidin-3-one

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Structure-function studies of acinetobactin analogs

Pathogenic Acinetobacter baumannii excrete the siderophore pre-acinetobactin as an iron-scavenging virulence factor. Pre-acinetobactin is a 2,3-dihydroxy-phenyl oxazoline that undergoes pH-dependent isomerization to the isooxazolidinone form acinetobactin in order to expand the pH range for iron acquisition by A. baumannii. In this study we establish important structure-function relationships for the kinetics of isomerization, iron(iii) binding, and siderophore utilization by A. baumannii. We showed that electronic properties of the phenyl oxazoline influence isomerization kinetics and iron(iii) binding. We found that iron(iii) chelation was directly correlated with A. baumannii utilization. Our studies provide important structural and mechanistic insight for understanding how pathogenic A. baumannii uses pre-acinetobactin as a 2-for-1 iron-scavenging siderophore virulence factor.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H1247NO – PubChem

 

Extracurricular laboratory:new discovery of Oxazolidin-2-one

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Synthesis of organic carbonates from alcoholysis of urea: A review

Organic carbonates are green compounds with a wide range of applications. They are widely used for the synthesis of important industrial compounds including monomers, polymers, surfactants, plasticizers, and also used as fuel additives. They can be divided into two main classes: cyclic and linear carbonates. Dimethyl carbonate (DMC) and diethyl carbonate (DEC) are the important linear carbonates. Carbonyl and alkyl groups present in DMC and DEC make them reactive and versatile for synthesizing various other important compounds. Ethylene carbonate (EC), glycerol carbonate (GC) and propylene carbonate (PC) are well-known cyclic organic carbonates. Phosgenation of alcohols was widely used for synthesis of organic carbonates; however, toxicity of raw materials restricted use of phosgenation method. A number of new non-phosgene methods including alcoholysis of urea, carbonylation of alcohols using CO2, oxy-carbonylation of alcohols, and trans-esterfication of alcohols and carbonates have been developed for synthesizing organic carbonates. Carbonylation of alcohols is preferred as it helps in utilization and sequestration of CO2, however, poor thermodynamics due to high stability of CO2is the major obstacle in its large scale commercialization. Oxy-carbonylation of alcohols offers high selectivity but presence of oxygen poisons the catalyst. Recently, alcoholysis of urea has received more attention because of its inexpensive abundant raw materials, favorable thermodynamics, and no water-alcohol azeotrope formation. Also, ammonia evolved in this synthesis route can be recycled back to urea by reacting it with CO2. In other words, this method is a step towards utilization of CO2as well. This article reviews synthesis of DMC, DEC, GC, PC, and EC from urea by critically examining various catalysts used and their performances. Mechanisms have been reviewed in order to give an insight of the synthesis routes. Research challenges along with future perspectives have also been discussed.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H989NO – PubChem

 

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Copper-catalyzed amidations of bromo substituted furans and thiophenes

The C-N cross-coupling reaction between aromatic halides and amides has now been applied to 2- and 3-substituted bromofurans and bromothiophenes. Catalytic CuI in the presence of N,N?-dimethylethylenediamine as a ligand and K3PO4 or K2CO3 as the base furnished 2- and 3-substituted amidofurans and thiophenes ranging from 11 to 99% depending on the particular amide source used.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H456NO – 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. Recommanded Product: Oxazolidin-2-one

Direct Metal-Free Entry to Aminocyclobutenes or Aminocyclobutenols from Ynamides: Synthetic Applications

The [2+2] cycloaddition of ynamides with the highly polarized reagent Tf2C=CH2has been developed to regioselectively afford bis(triflyl)aminocyclobutenes in the absence of catalyst under mild conditions. Incidentally, with the ynamides bearing electron-rich aromatic rings at the C-terminal, an interesting reactivity switch was observed; a cyclization/hydroxylation sequence yielded 2-amino-3-(triflyl)cyclobut-2-enols. Aminocyclobutene construction with addition of alcohols resulted in the formation of aminocyclobutenyl ethers through a cyclization/hydroalkoxylation process. Moreover, the utility of functionalized aminocyclobutenes as precursors for further elaboration was demonstrated with the preparation of alpha-amino-beta,gamma-unsaturated ketones and 3-(triflyl)buta-1,3-dien-2-amines through 4 pi-electrocyclic ring opening.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H284NO – PubChem

 

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A New <3 + 3>-Type Annelation Useful for the Formation of Piperidine Skeletons

A <3 + 3>-type annelation between alpha,alpha’-dimethoxylated amides 4 and allyltrimethylsilane (5) gave piperidine derivatives 6.It was applied to the synthesis of piperidine, indolizidine, quinolizidine, 1-azabicyclo<5.4.0>undecane, 1-aza-8-oxabicyclo<4.3.0>nonane, 8-azabicyclo<3.2.1>octane, and 9-azabicyclo<3.3.1>nonane derivatives.

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Reference£º
Oxazolidine – Wikipedia,
Oxazolidine | C3H988NO – PubChem