Archives for Chemistry Experiments of 15804-19-0

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A direct method for oxidizing quinoxaline, tetraazaphenanthrene, and hexaazatriphenylene moieties using hypervalent lambda3-iodinane compounds

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture. This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chemistry.

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Related Products of 15804-19-0, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 15804-19-0, molcular formula is C8H6N2O2, introducing its new discovery.

A three-dimensional copper(II) coordination polymer featuring the 2,3-dioxyquinoxalinate(-2) ligand: Preparation, structural characterization and magnetic study

The synthesis, single-crystal X-ray structure and magnetic properties of [Cu3L2Cl2(DMF)4]n (1), where L2- is the 2,3-dioxyquinoxalinate(-2) ligand, are reported. The complex was prepared by the reaction of CuCl2 and 1,4-dihydro-2,3-quinoxalinedione (H2L?) under basic conditions using either solvothermal or normal laboratory techniques. Compound 1 is a 3D coordination polymer with an (82.10)-a, lig (LiGe) topology, containing the ligand in a novel 3.1111 (Harris notation) coordination mode. Variable-temperature and variable-field magnetic studies reveal that the ligand L2- propagates weak antiferromagnetic exchange interactions through its “quinoxaline” part. IR data are discussed in terms of the structural features of 1 and the coordination mode of L2-.

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Studies in the syntheses of s-triazolo[4,3-a] quinoxalines

o-Phenylendiamine 1 is condensed with oxalic acid using Phillip’s procedure to obtain quinoxaline-2,3-doine 2, which on treatment with POCl3 gives the known 2,3-dichloroquinoxaline 3. 2-Chloro-3-hydrazinoquinoxaline 4 is prepared in a facile and simple way by treatment of 3 with hydrazine hydrate in methanol or in dioxane containing triethylamine. Condensation of 4 with a variety of aldehydes in DMF at room temperature furnishes the corresponding arylidene/alkylidine derivatives 5 which undergo smooth nucleophilic substitutions of chlorine by alkoxide or phenoxide ions yielding 2-alkoxy/phenoxy-3-(2-arylidene/alkylidene hydrazino) quinoxalines 6. The dehydrogenative cyclisation of 6 is achieved with chloranil in refluxing 1,2- dichloroethane resulting in s-triazole-[4,3-a] quinoxalines 7 whose structures are supported by spectral and analytical data and by alternate chemical synthesis in the case of the parent compound 7a.

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Microwave-assisted synthesis and antibacterial activity of some pyrazol-1-ylquinoxalin- 2(1H)-one derivatives

3-Hydrazinoquinoxalin-2(1H)-one was prepared from quinoxaline-2,3-dione and subsequently used for the synthesis of some potentially biologically active 3-(pyrazol-1-yl)quinoxalin-2(1H)-one derivatives. While 3-(3,5-dimethylpyrazol- 1-yl)quinoxalin-2(1H)-one showed a comparative effect with streptomycin, 3-(5-oxo-3-phenyl-4,5-di- hydropyrazol-1-yl)quinoxalin-2(1H)-one was found to be the most active with an MIC value of 7.8 mug/ml.

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An Efficient Synthesis of Quinoxalinone Derivatives as Potent Inhibitors of Aldose Reductase

A novel and facile synthesis of quinoxalinone derivatives was developed in which a wide range of 3-chloroquinoxalin-2(1H)-ones as key intermediates can be generated chemo- and regioselectively in good yields from corresponding quinoxaline-2,3(1H,4H)-diones. This new protocol is arguably superior, as it allows the design and preparation of a variety of bioactive quinoxaline-based compounds, which are particularly effective in the treatment of diabetes and its complications. Through this procedure, a new class of quinoxalinone-based aldose reductase inhibitors were synthesized successfully. Most of the inhibitors, with an N1-acetic acid head group and a substituted C3-phenoxy side chain, proved to be potent and selective. Their IC50 values ranged from 11.4 to 74.8nM. Among them, 2-(3-(4-bromophenoxy)-7-fluoro-2-oxoquinoxalin-1(2H)-yl)acetic acid and 2-(6-bromo-3-(4-bromophenoxy)-2-oxoquinoxalin-1(2H)-yl)acetic acid were the most active. Structure-activity relationship and molecular docking studies highlighted the importance of the ether spacer in the C3-phenoxy side chains, and provided clear guidance on the contribution of substitutions both at the core structure and the side chain to activity.

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The formation of overlooked compounds in the reaction of methyl amine with the diethyl ester of o-phenylenebis(oxamic acid) in MeOH

The treatment of the diethyl ester of o-phenylenebis(oxamic acid) (opbaH2Et2) with 2/3 of an equivalent of MeNH2 in MeOH does not result in the formation of the methyl ester of o-phenylene(N?-methyloxamide)(oxamic acid) (opooH3Me, 1) in pure state, as reported previously. The colourless crude material formed by this reaction was confirmed to be composed of 1 (89% content), the dimethyl ester of o-phenylenebis(oxamic acid) (opbaH2Me2, 2, 6%), 1,4-dihydro-2,3-quinoxalinedione (3, 3%) and o-phenylenebis(N?- methyloxamide) (opboH4Me2, 4, 1%), respectively. The identities of 1-4 have been verified by IR, 1H and 13C NMR spectroscopy as well as elemental analysis. In addition, the solid state structures of 1 and 2¡¤2DMSO, respectively, were determined by single-crystal X-ray diffraction studies. Successive recrystallization of the crude material from MeOH and MeOH : THF (1 : 1), respectively, does not give pure 1, but a mixture of 1 and 2. It is shown further that out of this mixture pure bis(oxamato) complexes cannot be obtained, as previously reported. Instead, treatment of the mixture with NiII or CuII salts, followed by the addition of [nBu4N]OH, results in the formation of two mixtures of [nBu4N]2[Ni(opba)] (5) and [nBu4N]2[Ni(opooMe)] (6) as well as [nBu4N]2[Cu(opba)] (7) and [nBu 4N]2[Cu(opooMe)] (8), respectively. The simultaneous formation of 5/6 and 7/8, respectively, has been verified by crystallization of the obtained mixtures and X-ray diffraction studies of the obtained single crystals. Co-crystallization of mixtures of 5/6 (99 mass%) and 7/8 (1 mass%), respectively, results in the formation of single-crystals of diamagnetically diluted 7 in the host lattice of 5 (7@5) accompanied by single-crystal formation of diamagnetically diluted 8 in the host lattice of 6 (8@6), as verified by EPR spectroscopy. It is finally shown that the ethyl ester of o-phenylene(N?- methyloxamide)(oxamic acid) (opooH3Et, 9), a homologue of 1, can be obtained in pure state by the treatment of opbaH2Et2 with 5/6 of an equivalent of MeNH2 in EtOH. The Royal Society of Chemistry 2013.

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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, 15804-19-0, name is Quinoxaline-2,3(1H,4H)-dione, introducing its new discovery. Application In Synthesis of Quinoxaline-2,3(1H,4H)-dione

Convergent functional groups. 9. Complexation in new molecular clefts

Two new 2,7-di-tert-alkyl-9,9-dimethylxanthene-4,5-dicarboxylic acids are prepared as organic soluble, U-shaped modules for the construction of molecular hosts. Condensation of two diacid units with spacers (e.g., hydroquinone, 4,4?-biphenol, and 2,6-diaminonaphthalene) gives large structures capable of assuming cleftlike shapes that complex sizable guests such as DABCO, quinine, quinidine, and quinoxaline-2,3-dione. The xanthene diacids and their derivatives are shown to contain intramolecular hydrogen bonds that organize the binding sites and modify their chemical properties.

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Experimental and ab initio calculational studies on 2,3-diketo- benzopiperazine

The title compound, 2,3-diketo-benzopiperazine, has been synthesized and characterized by elemental analysis, IR, electronic spectroscopy and single crystal X-ray diffraction. Ab initio calculations of the structure, natural bond orbital, topological analysis and thermodynamic functions of the title compound were performed at HF/6-311G** and B3LYP/6-311G** levels of theory. Vibrational frequencies were also predicted, assigned, compared with the experimental values, and they supported each other. Electronic absorption spectra were calculated by the time-dependent density functional theory, which indicates that the two absorption bands are mainly derived from the contribution of bands pi?pi*. The calculation of the second order optical non-linearity was carried out, and the molecular hyperpolarisability was 3.282¡Á10-30 esu.

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Synthesis and structure-activity relationships of 1,2,3,4- tetrahydroquinoline-2,3,4-trione 3-oximes: Novel and highly potent antagonists for NMDA receptor glycine site

A series of 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes (QTOs) was synthesized and evaluated for antagonism of NMDA receptor glycine site. Glycine site affinity was determined using a [3H]DCKA binding assay in rat brain membranes and electrophysiologically in Xenopus oocytes expressing 1a/2C subunits of cloned rat NMDA receptors. Selected compounds were also assayed for antagonism of AMPA receptors in Xenopus oocytes expressing rat brain poly-(A)+ RNA. QTOs were prepared by nitrosation of 2,4- quinolinediols. Structure-activity studies indicated that substitutions in the 5-, 6-, and 7-positions increase potency, whereas substitution in the 8- position causes a decrease in potency. Among the derivatives evaluated, 5,6,7-trichloro-QTO was the most potent antagonist with an IC50 of 7 nM in the [3H]DCKA binding assay and a K(b) of 1-2 nM for NMDA receptors expressed in Xenopus oocytes. 5,6,7-Trichloro-QTO also had a K(b) of 180 nM for AMPA receptors in electrophysiological assays. The SAR of QTOs was compared with the SAR of 1,4-dihydroquinoxaline-2,3-diones (QXs). For compounds with the same benzene ring substitution pattern, QTOs were generally 5-10 times more potent than the corresponding QXs. QTOs represent a new class of inhibitors of the NMDA receptor which, when appropriately substituted, are among the most potent glycine site antagonists known.

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Structure-activity relationships of 4-hydroxy-3-nitroquinolin-2(1H)- ones as novel antagonists at the glycine site of N-methyl-D-aspartate receptors

A series of 4-hydroxy-3-nitroquinolin-2(1H)-ones (HNQs) was synthesized by nitration of the corresponding 2,4-quinolinediols. The HNQs were evaluated as antagonists at the glycine site of NMDA receptors by inhibition of [3H]DCKA binding to rat brain membranes. Selected HNQs were also tested for functional antagonism by electrophysiological assays in Xenopus oocytes expressing either 1a/2C subunits of NMDA receptors or rat brain AMPA receptors. The structure-activity relationships (SAR) of HNQs showed that substitutions in the 5-, 6-, and 7-positions in general increase potency while substitutions in the 8-position cause a sharp reduction in potency. Among the HNQs tested, 5,6,7-trichloro HNQ (8i) was the most potent antagonist with an IC50 of 220 nM in [3H]DCKA binding assay and a K(b) of 79 nM from electrophysiological assays. Measured under steady-state conditions HNQ 8i is 240-fold selective for NMDA over AMPA receptors. The SAR of HNQs was compared with those of 1,4-dihydroquinoxaline-2,3-diones (QXs) and 1,2,3,4-tetrahydroquinoline-2,3,4-trione 3-oximes (QTOs). In general, HNQs have similar potencies to QXs with the same benzene ring substitution pattern but are about 10 times less active than the corresponding QTOs. HNQs are more selective for NMDA receptors than the corresponding QXs and QTOs. The similarity of the SAR of HNQs, QXs, and QTOs suggested that these three classes of antagonists might bind to the glycine site in a similar manner. With appropriate substitutions, HNQs represent a new class of potent and highly selective NMDA receptor glycine site antagonists.

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