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Synthesis of 1-(2-Hydroxyphenyl)-2,4-imidazolidinedione Derivatives through Cyclic Transformations of Ethyl 2-Oxo-3(2H)-benzoxazoleacetate Derivatives

A series of ethyl 2-oxo-3(2H)-benzoxazoleacetate derivatives 2 have been synthesized. By reaction with ammonia, primary amines or hydrazine, these compounds 2 were transformed into 1-(2-hydroxyphenyl)-2,4-imidazolidinedione derivatives 4, 5 and 6, respectively. Some of these new hydantoins 4, treated with phosphorus oxychloride, gave 3H-2-oxoimidazo[2,1-b]benzoxazole derivatives 9. Ethyl 2-oxo-3(2H)-benzoxazolepropionate (10) was prepared by a Michael reaction of ethyl acrylate with 2-benzoxazolone (1a). With 10, no cyclic transformation was observed in the presence of ammonia or alkylamine.

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Alpha2C adrenoreceptor agonists

In its many embodiments, the present invention relates to a novel class of phenylmorpholine and phenylthiomorpholine compounds useful as alpha2C adrenergic receptor agonists, pharmaceutical compositions containing the compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the alpha2C adrenergic receptor agonists using such compounds or pharmaceutical compositions.

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Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph3P-I2 Mediated Reactions of Benzo[ d]oxazol-2(3 H)-ones with Secondary Amines

Instead of the expected substituted 2-aminobenzo[d]oxazoles, relatively stable ring-opened oxyphosphonium betaines were isolated for the first time from the Ph3P-I2-mediated reactions of benzo[d]oxazol-2(3H)-ones with acyclic secondary amines. The structure of one of these compounds was unambiguously confirmed by single-crystal X-ray analysis. Thermolysis of the betaines gave rise to 2-dialkylaminobenzoxazoles with concomitant loss of triphenylphosphine oxide, suggesting their possible role as intermediates in an alternative reaction path.

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Brief introduction of 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

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Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase

Inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL) are generated by replacing the acyl phosphate group of biotinyl-5?-AMP with either a 1,2,3-triazole (see 5/10a/10b) or a 1,2,4-oxadiazole (see 7) bioisostere. Importantly, the inhibitors are inactive against the human BPL. The nature of the 5-substituent in the component benzoxazolone of the optimum 1,2,3-triazole series is critical to activity, where this group binds in the ATP binding pocket of the enzyme.

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A Simple Synthesis of 2(3H)-Benzoxazolones using Phenyl Chloroformate

2(3H)-Benzoxazolones 3 can be prepared directly from the corresponding 2-aminophenols and phenyl chloroformate.The intermediate 2-hydroxy phenylcarbamates 2 are formed easily in aqueous alcohol solvent and these are converted rapidly to product, without their isolation, using one equivalent of sodium hydroxide.The synthesis accommodates a wide variety of substituents, including the easily hydrolyzed ethyl ester.

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More research is needed about 5-Nitro-2,3-dihydro-1,3-benzoxazol-2-one

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Synthesis of benz[d]oxazolones involving concomitant acetyl migration from oxygen to nitrogen

Heating of o-acetoxybenzoyl azides 6-10 in toluene leads to the Curtius reaction, which, when followed by closure of oxazolone ring with concomitant migration of acetyl group from oxygen to nitrogen, produces 3-acetoxybenz[d] oxazol-2(3H)-ones 11-15, which undergo hydrolysis with hot dilute hydrochloric acid to furnish benz[d]oxazol-2(3H)-ones 17-21. Thermal reaction of 2-hydroxy-5-nitrobenzoyl azide (22) in toluene finally yields a mixture of 5-nitrobenz[d]oxazol-2(3H)-one (20) and 5-nitrobenz[d]isoxazol-3(2H)-one (23). Copyright Taylor & Francis Group, LLC.

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Properties and Exciting Facts About 3889-13-2

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Modified benzoxazolone derivative as 18-kDa TSPO ligand

We have synthesized six new congeners of acetamidobenzoxazolone for Translocator Protein [18 kDa, TSPO] imaging. The best in vitro binding affinity (10.8?¡À?1.2?nm) for TSPO was found for N-methyl-2-(5-(naphthalen-1-yl)-2-oxobenzo[d]oxazol-3(2H)-yl)-N-phenylacetamide, (NBMP). NBMP was synthesised by Suzuki coupling reaction between 2-(5-bromo-2-oxo-1,3-benzoxazol-3(2H)-yl)-N-phenylacetamide and napthalene-1-boronic acid. Computational docking and simulation studies showed not much impact of intersubject variability on binding which is one of the major drawbacks of several TSPO ligands. These findings suggested that NBMP may become a promising marker for visualization of neuroinflammation via TSPO targeting.

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Synthesis of Substituted 2-Phenylbenzoxazoles as CNS Active Agents

The reaction of hydrazine (III) with CS2 and ethanolic KOH furnishes 2-<2'-(benzoxazolyl)phenoxymethyl>-5-mercaptooxadiazole (IV) which on Mannich reaction with piperidine and morpholine gives the bases Va and Vb respectively.Condensation of isatin and 5-chloroisatin with III affords VI and VII which on Mannich reaction furnish the bases VIII and IX respectively.Condensation of N-methylisatin and N-methyl-5-chloroisatin with III gives X and XI.Treatment of 2-(p-hydroxyphenyl)benzoxazole (I) with allyl bromide furnishes the allyl derivative (XII) while acetylation of it with Ac2O gives XIII.Mannich reaction of benzothiazolin-2-thione, benzoxazolin-2-one and 6-nitrobenzoxazolin-2-one with 2-(p-aminophenyl)benzoxazole (XIV) affords the compounds XV, XVIa and XVIb, respectively.Treatment of acetanthranil (XVII) with XIV gives 3--2-methyl-4-quinazolone (XVIII).Condensation of isatin and N-methylisatin with XIV furnishes XIX and XX respectively.The former (XIX) on Mannich reaction with morpholine and formaldehyde gives rise to XXI.

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The vicarious nucleophilic substitution of hydrogen and related reactions in nitrobenzoxazoles

5- and 6-nitrobenzoxazoles 3 and 4 react with nucleophiles exclusively at C-2, giving ring opening products. If position 2- is blocked with phenyl substituent the reaction takes place in the carbocyclic ring affording the VNS products. 2-Methylthio-5-nitrobenzoxazole 7 and its 6-nitro isomer 8 give products which result from addition of a nucleophile to the carbocyclic ring (VNS) as well as to the heterocyclic ring (S(N)Ar and ring cleavage). 2-Methylthiobenzoxazoles can be readily converted to the corresponding benzoxazolones via oxidative hydrolysis.

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2, 4 -DIAMINOPYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS

The present invention relates to novel pyrimide derivatives of formula (I): that are useful as kinase inhibitors. More particularly, the present invention relates to novel pyrimidine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders

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