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Synthesis of some new tetrazolo- [1,5-a]quinazolino[2,3-c]imidazo- [4,5-b]quinoxaline derivatives as antimicrobial agents

Treatment of 6,7-dimethoxy-2-chloroquinazolin-4-amine 1 and 7,8-dimethoxy tetrazolo-[1, 5-a]-quinazolin-5-amine 4 with 2, 3- dichloroquinoxaline 2a-e in glacial acetic acid /DMF afford corresponding substituted 6,7-dimethoxy-2- chloroquinazolo[3,4- c]-imidazo-[4,5-b]-quinoxalines 3a-e and 7,8-dimethoxytetrazolo- [1,5-a]-quinazolo-[2,3-c]-imidazo-[4,5-b]-quninoxalines 5a-e. The chemical structures of the newly synthesized compounds have been characterized by IR, NMR, mass spectral and CHN analysis. All the title compounds are subjected to in vitro antibacterial testing against two pathogenic strains and antifungal screening against two fungi. Among the tested compounds, 5b and 5c show significant antibacterial and antifungal activities. Also the compound 3b show significant antifungal activity against Candia albicans.

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Air-stable P-chiral bidentate phosphine ligand with (1-adamantyl) methylphosphino group

Air-stable diphosphine ligand, (R,R)-2,3-bis((1-adamantyl)-methylphosphino) quinoxaline, was prepared by the reaction of enantiomerically pure (S)-(1-adamantyl)methylphosphine-borane with 2,3-dichloroquinoxaline. The ligand exhibited excellent enantioselectivities in Rh-catalyzed asymmetric hydrogenation and Pd-catalyzed asymmetric ring-opening reaction. Copyright

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Survey of the electrochemical behavior of chlorinated pyrazines, quinoxalines, and pyridazines at carbon and mercury cathodes

Cyclic voltammetry and controlled-potential electrolysis have been employed to examine the electrochemical behavior of some mono- and dichlorinated pyrazines, quinoxalines, and pyridazines at carbon and mercury cathodes in either acetonitrile or dimethylformamide containing a tetraalkylammonium salt. Unsubstituted pyrazine and pyridazine each exhibit a single reduction wave, whereas unsubstituted quinoxaline shows three cathodic waves. For the chlorinated compounds, an additional wave is seen for the reduction of each carbon-chlorine bond. Depending on the potential of the cathode, bulk electrolyses of dichlorinated pyrazines or quinoxalines afford either the monochlorinated or fully dechlorinated product, whereas the monochlorinated analogues undergo reduction to the dechlorinated species. Electrolyses of chlorinated pyridazines give dark colored solutions, but the products (apparently polymeric) cannot be detected or identified by means of conventional GC, GC-MS, and HPLC techniques.

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Transition metal free hydrolysis/cyclization strategy in a single pot: Synthesis of fused furo N-heterocycles of pharmacological interest

A transition metal free tandem two-step strategy has been developed involving hydrolysis of 2-chloro-3-alkynyl quinoxalines/pyrazines followed by in situ cyclization of the corresponding 2-hydroxy-3-alkynyl intermediates in a single pot leading to fused furo N-heterocycles as potential inhibitors of sirtuins. A representative compound showed promising pharmacological properties in vitro and in vivo.

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Imidazo[1,2-a]quinoxalin-4-amines: A novel class of nonxanthine A1- adenosine receptor antagonists

The syntheses and A1 adenosine receptor affinities of a number of imidazo[1,2-a]quinoxalin-4-amines are reported. Structure-activity relationships within the series and in comparison with other similar tricyclic nonxanthine adenosine antagonists are discussed, leading to a putative common binding mode of these nitrogen-containing heterocycles to A1 adenosine receptors. Secondary amino compounds displayed the best affinities toward A1 receptors, while the tertiary amines were almost devoid of activity, thus suggesting a crucial role for the hydrogen bond-forming 4-NH group. Remarkably higher potencies for 1-methyl and N-cyclopentyl derivatives were also found. 4-Cyclopentylamino-1-methylimidazo[1,2-a]quinoxaline (IRFI 165) is the most potent compound in this series, having K(i)(A1) = 7.9 nM. It is also provided with a good A1 selectivity both versus A(2a) and A3 subtypes and was selected for further pharmacological studies.

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New derivatives of quinoxaline – Syntheses, complex formation and their application as controlling ligands for zinc catalyzed epoxide-CO2-copolymerization

A series of amino-(type 3) as well as hydrazino-substituted quinoxalines (type 8) have been synthesized in order to study their ability to complex with iron(III) and zinc(II) ions. Cyclization of 2,3-dichloroquinoxaline (1) with a bis-amidine 9 leads to ring-fused quinoxalines of type 10. One of these compounds (10a) forms a unique macrocyclic hexameric complex 14 with zinc ions in the presence of 2,6-diisopropyl phenolate. In an analogous manner, the monomeric complexes 12 and 13 could be synthesized. All of these new zinc complexes catalyze the copolymerization of cyclohexene oxide and carbon dioxide with a high degree of selectivity in the resulting polymers.

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A new approach to construct a fused 2-ylidene chromene ring: Highly regioselective synthesis of novel chromeno quinoxalines

Regioselective construction of a fused 2-ylidene chromene ring was achieved for the first time by using AlCl3-induced C-C bond formation followed by Pd/C-Cu mediate coupling-cyclization strategy. A number of chromeno[4,3-b]quinoxaline derivatives were prepared by using this strategy. Single crystal X-ray diffraction study of a representative compound e.g. 6-(2,2-dimethylpropylidene)-4-methyl-6H-chromeno[4,3-b]quinoxalin-3-ol confirmed the presence of an exocyclic C-C double bond with Z-geometry. The crystal structure analysis and hydrogen bonding patterns of the same compound along with its structure elaboration via propargylation followed by Sonogashira coupling of the resulting terminal alkyne is presented. A probable mechanism for the formation of 2-ylidene chromene ring is discussed. Some of the compounds synthesized showed anticancer properties when tested in vitro.

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Static and Dynamic Properties of Quinoxalines in the Phosphorescent Triplet State from Optically Detected Magnetic Resonance

The static and dynamic properties of the phosphorescent triplet states of quinoxaline and 2,3-disubstituted derivatives in hexane have been studied at 1.4 K using the methods of optically detected magnetic resonance.In addition, the absorption and phosphorescence excitation spectra have also been measured to attain the information about the low lying excited states.A systematic comparison has been made for the purpose of examining the effect of substitution.A significant enhancement of the pumping rates for the y spin sublevel observed in the chlorine-substituted derivatives is concluded to be due to the additional indirect process of intersystem crossing which occurs from S1 of n,?* to T1 passing through the intermediate triplet state of ?,?*.A detailed discussion on the observed phosphorescence spectra originating from the three sublevels has achieved a satisfactory success in understanding the mechanisms responsible for the radiative decay processes.It is concluded that the mechanisms due to vibronic coupling with closely lying n,?* triplet states are of little importance in the systems studied here.

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Bridgehead nitrogen heterocycles: Synthesis and reactions of S-triazolothiadiazinyl and S-triazolothiadiazolylquinoxalines

The reaction of 3(4-amino-5-mercapto-1,2,4-triazol-3′-yl)quinoxalin-2(1H)-one 4 with phenacyl bromide, 2,3-dichloroquinoxaline, benzoine, chloroacetic acid, and alpha-chloroacetonitrile to give triazolothiadiazino derivatives 5-10. Reaction of 4 with phenyl isothiocyanate, aromatic aldehydes, formic acid, aromatic carboxylic acid, benzoyl chloride, and carbon disulphide gave triazolothiadiazino derivatives 11-17.

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A kind of 2-hydrazone-thiazolo [4,5-b] quinoxaline compound and its preparation and use (by machine translation)

The invention relates to 2-hydrazone-thiazolo[4,5-b]quinoxaline compounds which are characterized in that the compounds have a general formula represented as the following, wherein R is as the following. The 2-hydrazone-thiazolo[4,5-b]quinoxaline compounds provided by the invention can be used as potential antibacterial and antitumor medicines. The invention also discloses a preparation method thereof.

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