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Intermolecular [2+2] photocycloaddition reactions between 3-(2-oxo-2H-chromene-3-carbonyl)oxazolidin-2-one with n-propyl vinyl ether and vinyl pivalate were carried out to give [2+2] cycloadducts in excellent yield with perfect regioselectivity. A Lewis acid catalyst (30 mol%) was moderately effective in accelerating the reaction. Furthermore, enantioselective reactions catalyzed by chiral Lewis acid catalysts (30 mol%) were performed to give cycloadducts in excellent yields with up to 13% ee.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H650NO – PubChem

 

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Starting with D- and L-serines, an expedient method for the preparation of oxazolidinyl piperidines, azepenes and azacyclooctenes was illustrated as a route to various deoxy-azasugars and hydroxypyrrolizidines. The ring-closing olefin metathesis of oxazolidinyl di-olefins was used as a key-step to construct the azacycles. Consecutive epoxidation, hydrolysis and transannulation of oxazolidinyl azacyclooctene led to hydroxypyrrolizidines.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H1481NO – PubChem

 

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In the present study, in order to synthesize broad-spectrum antibacterial agents, we coupled both the oxazolidinone and novel thiophene chalcone derivatives by using Buchwald’s protocol under ultrasound irradiation. All the newly synthesized 20 oxazolidinone-thiophene chalcone hybrid compounds were characterized by IR,1HNMR and Mass spectral analysis and evaluated for in vitro antibacterial and antifungal activities. Antibacterial and antifungal activities were tested using the serial dilution method. The test compounds 7e to 7g exhibited very high activities at 3.125 mug/ml when compared to the standard drug linezolid and were as other compounds showed moderate to weak activities. In case of antifungal activities, the test compounds 7e to 7g, 7i,7j, and 7m to 7o exhibited moderate activities compared to the standard fluconazole, whereas the rest of the compounds showed weak activities against tested fungal strains. The binding mode analysis of the test compounds 7e to 7g were investigated by the docking studies using Glide 6.6., inside the active site of peptidyl transferase center of E.coli ribosome (PDB ID: 2AW4), revealed that the experimental results were comparable to that of co-crystallized ligand linezolid.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H1448NO – PubChem

 

The important role of (4S,5R)-4-Methyl-5-phenyloxazolidin-2-one

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A visible light-mediated [2+2] photocycloaddition of amide-linked dienes using [Ir(dtb-bpy)(dF(CF3)ppy)2]PF6 as triplet sensitizer was applied to generate a variety of N-tert-butyl, N-benzyl- and N-tert-butoxycarbonyl-protected 3-aza-bicyclo[3.2.0]heptan-2-ones in good yields and with good diastereoselectivity. Density functional theory calculations shed light on the conformational prerequisites for the [2+2] photocycloaddition. The bicyclic key structures could be readily transformed into g-cyclobutane amino acids. For the obtained racemic 3-phenyl-2-aminocyclobu-tane-1-carboxylic acid the resolution with chiral oxazolidin-2-one is demonstrated to allow access to both enantiomers. Alternatively, a chiral auxiliary approach led as well to the enantiomerically pure target compound. Finally, the synthesis of either enantiomer of 3-(aminomethyl)-5-phenylpentanoic acid, the racemate being described as an anticonvulsant is described.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H2175NO – PubChem

 

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A heterocyclic compound represented by formula (I): STR1 wherein R1 represents a hydrogen atom, an alkyl group, an aryl group which may be substituted with one or more substituents selected from the group consisting of a halogen atom, an alkoxy group, an alkyl group and a trihalogenomethyl group; lambda represents 0 or 1; ring A represents a 6 membered heterocyclic ring containing the nitrogen atom shared with the triazine ring and which may contain one or more double bonds; Y represents a substituted or unsubstituted alkylene group having 1 to 15 carbon atoms; and Q represents a group represented by formula (II): STR2 wherein R2, R3, R4 and R5 are represented by substituents disclosed herein; or salt thereof, and intermediates therefor are described. The compound of formula (I) or salt thereof exhibit selective serotonin 2-receptor antagonistic activity and are useful for the prevention or treatment of circulatory diseases, e.g., ischemic heart diseases, cerebral vessel disturbances, and peripheral circulation disturbances.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H244NO – PubChem

 

New explortion of (R)-4-Benzyl-2-oxazolidinone

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A general and efficient method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C-N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry, this atom economical synthesis of ynamides should invoke further attention from the synthetic organic community.

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Oxazolidine – Wikipedia,
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We have shown that sulfuryl chloride is an efficient reagent for the conversion of 2-oxazolidinone into the dichloro derivative, N-acetyl-4,5- dichloro-2-oxazolidinone. Subsequent Zn/AcOH reductive dehalogenation of this trans-dichloride gives N-acetyl-2-oxazolone. The dichloride was previously reported as an undesired side product in the preparation of N-acetyl-2-oxazolone from the monochloro oxazolidinone. In our hands, the dichloride is a key intermediate in a new synthesis of 2-oxazolone, that avoids the use of chlorine gas. Georg Thieme Verlag Stuttgart.

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Oxazolidine – Wikipedia,
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N-Acyl-2-phenyliminooxazolidines 7 were easily prepared and treated with several amines at room temperature, yielding amides 9 in very high yields.Possible mechanisms for this transformation are briefly discussed.

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Oxazolidine – Wikipedia,
Oxazolidine | C3H545NO – PubChem

 

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A four-step route to the tetracyclic ring system found in a number of indole alkaloids is described using stereoselective dipolar cycloaddition reactions of azomethine ylides. The ylides were derived from N-protected 2-butenylindole-3-carbaldehydes, which were prepared in three steps from 2-methylindole. Condensation of these aldehydes with a variety of alkylamino esters or amino acids or with N-methylhydroxylamine gave the required azomethine ylides or nitrone that undergo intramolecular cycloaddition onto the pendant, unactivated alkene. The cycloaddition sets up two new rings and up to three new stereocentres stereoselectively. After cycloaddition with N-allylglycine, N-deallylation provided the N-unsubstituted product and this constitutes a formal synthesis of the alkaloid deethylibophyllidine. The cycloaddition chemistry was also shown to be amenable as a route to the alkaloid ibophyllidine or epiibophyllidine, although the use of 2-(allylamino)butyric acid to prepare the azomethine ylide can favour competing iminium ion isomerisation and hydrolysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Reference:
Oxazolidine – Wikipedia,
Oxazolidine | C3H448NO – PubChem