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Compounds of the formula STR1 wherein R1 is hydrogen, alkali metal, alkyl, substituted alkyl, alkylsulfenyl or acyl; R2 is alkyl or cyclopropyl; R3 is hydrogen, chlorine, bromine or fluorine; n and p are 0 or 1 and A is a mineral acid are useful as fungicides. A representative compound is 6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline.

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The oxidation reaction of a series of quinoxaline derivatives, using KMnO4 in the presence or absence of NaOH, are described.Neutral oxidation of 2-chloro- and 2,3-dichlorodioxalines 2-4 afforded the corresponding chloro- and dichloropyrazinedicarboxilic acids 13 and 14 in good yield.On the other hand, oxidation of quinoxalin-2(1H)-one and 1,4-dihydroquinoxaline-2,3-dione derivatives in alkaline medium gave different products, with the quinoxalin-2(1H)-one (5) forming 1,4-dihydroquinoxaline-2,3-dione (9), while various substituted quinoxalin-2,3-dione derivatives (see 9-11) gave a new type of dimeric products.The structural assignments for the new compounds were based on spectroscopic data.

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The hydrogenation of 2,3-dimethylpyrazino<2,3-b>quinoxaline 1 and 2-phenylpyrazino<2,3-b>quinoxaline 2 leads to the corresponding 5,10-dihydroderivatives 3b and 4b.LiAlH4 reduction of 2, of 2,3-dimethyl-6,7-diphenylpyrazino<2,3-b>pyrazine 8 and 2,6,7-triphenylpyrazino<2,3-b>pyrazine 9 furnishes the corresponding 1,2,3,4-tetrahydroderivatives 7, 10 and 11.NaBH4 reduction of 2 leads to a mixture of 4b and 7.In hydroorganic medium 1 and 2 are electrochemically reduced to 3b and 4b with which they form a redox system.

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A novel series of quinoxaline derivatives, as Multi-Target-Directed Ligands (MTDLs) for AD treatment, were designed by lending the core structural elements required for H3R antagonists and hybridizing BACE 1 inhibitor 1 with AChE inhibitor BYYT-25. A virtual database consisting of quinoxaline derivatives was first screened on a pharmacophore model of BACE 1 inhibitors, and then filtered by a molecular docking model of AChE. Seventeen quinoxaline derivatives with high score values were picked out, synthesized and evaluated for their biological activities. Compound 11a, the most effective MTDL, showed the potent activity to H3R/AChE/BACE 1 (H3R antagonism, IC50 = 280.0 ± 98.0 nM; H3R inverse agonism, IC50 = 189.3 ± 95.7 nM; AChE, IC50 = 483 ± 5 nM; BACE 1, 46.64 ± 2.55% inhibitory rate at 20 muM) and high selectivity over H1R/H2R/H4R. Furthermore, the protein binding patterns between 11a and AChE/BACE 1 showed that it makes several essential interactions with the enzymes.

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Polysubstituted o-phenylenediamines were synthesised in moderate to high yield by reductive cleavage of the corresponding 2H-benzimidazole-2-spirocyclohexane with sodium dithionite in aqueous ethanol and converted into methyl benzimidazole-2-carbamates and 2-methylthio- and 2-trifluoro-methylbenzimidazoles with known or potential anthelminthic activity. 5-(Pyrimidin-2-ylthio)-benzimidazole and 11-(pyridin-2-ylthio)dibenzo[a,c]phenazine were synthesized too. Attempts to oxidise 1,3-dihydro-2H-4,9-diazanaphth[2,3-d]imidazole, prepared by condensation of 2,3-diaminoquinoxaline with cyclohexanone, to an analogue of the title system failed.

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Reaction of 2,3-bis(neopentylamino)quinoxaline (1) with nBuLi and GeCl4 or GeCl2·(dioxane) (molar ratio 1:2:1) in THF furnished highly moisture-sensitive Ge(IV) and Ge(II) heterocycles 2a and 3a, respectively. The quinoxaline-annulated N-heterocyclic germylene (quinNHGe) 3a is stable only in the presence of Li(THF)x and exhibits electrophilic properties associated with the strongly electron-withdrawing annulation. Coordination of chloride at Ge(II) and of Li+ at nitrogen is assumed, as found in crystals of a bis(quinoxaline)-annulated eight-membered NHGe LiCl adduct. Addition of dineopentyl-benzimidazol-2-ylidene (bnNHC) provides a labile bnNHC-quinNHGe adduct 4 as indicated by strong downfield coordination shift of the NMR signal for the carbene donor atom. Attempts to grow single crystals led to decomposition and protonation of the carbene forming the bis(benzimidazolium) salt 5 with Li2 (THF)2 Cl42 – anion. Introduction of 2-methoxyethyl or 2-dimethylaminoethyl side arms as chelating functional groups into the diaminoquinoxalines 6 and 7 and subsequent reaction with 2 nBuLi/GeCl2·(dioxane) did not markedly stabilize the resulting donor-substituted quinNHGe 8 and 9. Related silicon (2b) and tin heterocycles (3c) were synthesised for comparison. The quinoxaline-annulated N-heterocyclic stannylene 3c exhibits an extreme 119Sn upfield shift compared to other N-heterocyclic stannylenes, suggesting higher coordination at tin.

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Benzofuroxan (1) reacts with phosphorus ylide 2 to give benzimidazole derivatives 8 and 10, whereas reaction of 1 with ylide 12 furnishes quinoxaline 17 via an initial Wittig-type reaction.Similarly the reaction between the furoxano<3,4-b>quinoxalines 19a or 19b and the ylide 2 yielded compounds 22a and 22b, respectively.In these reactions as well as in the reactions of the above furoxans with other phosphorus ylides, a significant deoxygenation of the furoxans to furazans with subsequent oxidation of the ylides is generally observed.

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The present invention relates to novel colorants based on bisanthraquinone azamethine derivatives or their metal complexes for the mass coloring of polymers, either for polar polymers such as polyamides, polyesters, polycarbonates and ABS; or for non-polar polymers such as polyethylene and polypropylene.The novel colorants are characterized by i) a central substituted or unsubstituted annealed aromatic ring system comprising at least one heteroatom and ii) two anthraquinone moieties attached thereto by azamethine bridges.The novel colorants provide for excellent compatibility with the polymer substrate, excellent heat stability and light fastness.

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Three new alpha,alpha?-diimine ligands were synthesized based on condensation of 1,10-phenanthroline-5,6-dione with 1,2-phenylenediamine derivatives using different approaches. All compounds were fully characterized by IR, 1H and 13C NMR, UV-visible, and MS spectroscopies. We report the first example of a dipyrido[3,2-f:2?,3?-h]quinoxalino[2,3-b]quinoxaline, which exhibits a strong absorption at 430 nm and an interesting electrochemical behavior. These new molecules may have biological potential and are of synthetic and technological importance.

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The reactions of imidazoquinoxaline and 1,3,5-H3btc acid under different condition have been investigated. The different degree of hydrolysis reaction leads to two different adducts being produced, namely, [(HdiamQuin)+(H2btc)-] (1), and [(diamQuin)4(ImiQuin)·4H2O] (2). Both compounds were characterized by X-ray crystallography. Crystal data for 1: monoclinic, space group Pn with a = 9.868(2), b = 5.3172(11), c = 15.387(3) A, beta = 91.10(3), C17H14N4O6, Mr = 370.32, V = 807.2(3) A3, Z = 2, Dc = 1.524 g/cm3, mu(MoKalpha) = 0.118 mm-1, F(000) = 384, the final R = 0.0385 and wR = 0.0869 for 2294 observed reflections (I > 2sigma(I)). Crystal data for 2: triclinic, space group P-1 with a = 9.825(2), b = 14.144(3), c = 16.054(3) A, alpha = 101.06(3), beta = 102.55(3), gamma = 92.46(3), C44H40N20O4, Mr = 912.96, V = 2128.8(7) A3, Z = 2, Dc = 1.424 g/cm3, mu(MoKalpha) = 0.099 mm-1, F(000) = 952, the final R = 0.0554 and wR = 0.1662 for 6563 observed reflections (I > 2sigma(I)). X-ray diffraction analysis reveals that compound 1 is a salt. Imidazoquinoxaline was wholly hydrolyzed into 2,3-diaminoquinoxaline and protonated as a cation with H2btc- acting as an anion. However, in compound 2, the imidazoquinoxaline is only partly hydrolyzed, and the resulting 2,3-diaminoquinoxaline forms adduct with the intacted imidazoquinoxaline. Both are further aggregated into 3D frameworks by strong hydrogen bonding even pi-pi interactions.

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