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Electrophilic cyclizations of 2,3-dialkynylquinoxalines and 1, 2-dialkynylbenzenes: A comparative study

The reactivity of 2,3-dialkynylquinoxalines towards electrophiles (Br 2, I2, ICI, NBS, HBr) has been studied. All tested reactions, except one with HBr, start with the addition of an electrophile to the carbon-carbon triple bond that promotes further 5-exo-dig carbocyclization ultimately yielding a mixture of stereoisomeric cyclopenta[b]quinoxaline derivatives. The nature of substituents on the C=C bonds of the starting molecule influence the stereochemical result of the reaction. The ratio of isomeric cyclization products also depends on the electrophile used. ortho-Dialkynylbenzenes and ortho-dialkynylquinoxalines demonstrate rather similar reactivity towards halogen electrophiles, but differ in their reactions with hydrobromic acid, which is caused by the basic nature of the aza group of the quinoxaline substrate.

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The synthesis of potential DNA intercalators. 2. Tri- and tetra-cyclic heterocycles

The reaction of 1,4-dichlorophthalazine and 2,3-dichloroquinoxaline with some isoxazolones gave their mono- and bis-isoxazolinyl derivatives. The base-catalyzed rearrangement of these derivatives afforded the corresponding tri- and tetracyclic heterocycles.

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Archives for Chemistry Experiments of 5-Nitroquinoxaline

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Selective Synthesis of Benzo[a]Carbazoles and Indolo[2,1-a]-Isoquinolines via Rh(III)-Catalyzed C?H Functionalizations of 2-Arylindoles with Sulfoxonium Ylides

A highly chem- and regioselective synthesis of diversely substituted benzo[a]carbazoles and indolo[2,1-a]-isoquinolines through Rh(III)-catalyzed cascade reactions of 2-arylindoles with sulfoxonium ylides is presented. To be specific, treatment of 2-arylindoles, 2-arylindole-3-carbaldehydes, 2-arylindole-3-carbonitriles or 2-aryl-3-methylindoles with sulfoxonium ylides under the catalysis of Rh(III) led to the selective formation of 6-aryl/alkyl benzo[a]carbazoles, 5-acylbenzo[a]carbazoles, 6-amino-5-acylbenzo[a]carbazoles or 12-methylindolo[2,1-a]isoquinolines, respectively. Mechanistically, the formation of the title compounds involves a cascade process including metalation of the inert C(sp2)?H bond, migratory insertion of ylide into the carbon-metal bond via an in situ carbenoid formation, protodemetalation, and condensation. To our knowledge, this is the first example in which beta-carbonyl sulfoxonium ylides were used as stable carbene precursors and bifunctional C2 synthons to afford benzo[a]carbazoles and indolo[2,1-a]isoquinolines. (Figure presented.).

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Anti-quorum and DNA cleaving agent

The anti-quorum and DNA cleaving agent is directed to a ruthenium complex formulated from dichloro-(eta6-p-cymene) ruthenium(II) dimer and 2-chloroquinoxaline, the complex having the formula: The reaction cleaves the dimer, leaving a half-sandwich ruthenium complex with an eta6 coordination bond to the arene ligand and an Ru?N bond attaching the chloroquinoxaline to the ruthenium complex. The agent has an anti-quorum sensing effect on bacteria, inhibiting the formation of biofilm and inhibiting bacterial virulence. The agent also binds to DNA and may cleave the DNA, e.g., at the N7 base pair of guanine, due to a hydrolytic mechanism, suggesting potential use as an anticancer or antitumor agent.

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18514-76-6, Name is 5-Nitroquinoxaline, belongs to quinoxaline compound, is a common compound. Computed Properties of C8H5N3O2In an article, once mentioned the new application about 18514-76-6.

Internal Oxidant-Triggered Aerobic Oxygenation and Cyclization of Indoles under Copper Catalysis

A concise synthesis of pyrazolo[1,5-a]indole derivatives by copper-catalyzed aerobic oxygenation and cyclization of indoles with oxime acetates is described. This protocol represents an elegant example of N-1, C-2, and C-3 tri-functionalization of indoles in one-pot. Mechanistic studies indicate the reaction proceeds through a radical procedure. Oximes as an internal oxidant have been demonstrated to be a driver to initiate aerobic oxidation, which provides a new oxidative pattern for C-H functionalization even with high atom- and step-economy.

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Discovery of pyrrolo[2,1-f][1,2,4]triazine C6-ketones as potent, orally active p38alpha MAP kinase inhibitors

Pyrrolo[2,1-f][1,2,4]triazine based inhibitors of p38alpha have been prepared exploring functional group modifications at the C6 position. Incorporation of aryl and heteroaryl ketones at this position led to potent inhibitors with efficacy in in vivo models of acute and chronic inflammation.

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Final Thoughts on Chemistry for Quinoxaline-2,3(1H,4H)-dione

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Solvent-free reaction using phosphonium salts: Chlorination of hydroxyheteroaromatics and dehydration of primary amides

Solvent-free chlorination of heteroaromatics using the phosphonium salt, prepared by reaction of triphenylphosphine with N-chlorosuccinimide, was accomplished by microwave-irradiation or heating to give the corresponding chloroheteroaromatics. Similarly, primary amides was converted into nitriles by this method.{A figure is presented}.

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Discovery of 2,3-Dichloroquinoxaline

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Heterocyclic Systems Containing Bridgehead Nitrogen Atom: Synthesis of 2,3-Dihydrothiazolo<3',2':2,3><1,2,4>triazino<5,6-b>indole, 4H-2,3-Dihydro<1,3>thiazino<3',2':2,3><1,2,4>triazino<5,6-b>indole and Related Heterocycles

8-Bromo-5H-2,3-dihydro-1,2,4-triazino<5,6-b>indole-3-thione (II) on condensation with 1,2-dibromoethane and 1,3-dibromopropane gives the cyclized products 7-bromo-2,3-dihydrothiazolo<3',2':2,3><1,2,4>triazino<5,6-b>indole (III) and 4H-8-bromo-2,3-dihydro<1,3>thiazino<3',2':2,3><1,2,4>triazino<5,6-b>indole (IV) respectively, and not the angular isomers VI and VII.The unequivocal synthesis of the latter (VI and VII) has been accomplished by the reaction of 5-bromoisatin-3-thiosemicarbazone (I) with 1,2-dibromoethane and 1,3-dibromopropane respectively.Condensation of II with 2,3-dichloroquinoxaline on the other hand, yields the angular isomer 3-bromoquinoxalino<2',3':4,5>thiazolo<2,3-c>indolo<2,3-e><1,2,4>triazine (V), identical with a sample obtained unambigously by the reaction of I with 2,3-dichloroquinoxaline.

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The important role of 2,3-Dichloroquinoxaline

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2-amino-1,2,3-triazole derivatives from vicinal diazides

A unique 2-amino-1,2,3-triazole system has been synthesized by the reaction of a vicinal diazide with triphenylphosphine. The crystal structures of five 2-amino-1,2,3-triazole systems, a ditetrazole and a Staudinger adduct are reported. Ab initio calculations are used to rationalize the structures and properties of these materials, and possible reaction pathways are discussed.

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Can You Really Do Chemisty Experiments About 2-Chloroquinoxaline

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Synthesis of new arylaminoquinoxalines and their antimalarial activity in mice

2-Arylaminoquinoxalines were prepared by the condensation of 2-chloroquinoxaline with the appropriate Mannich bases in the presence of HCI. To synthesize the Mannich bases, 4-acetamidophenol was reacted with formaldehyde and dialkylamine to yield 3-[(dialkylamino) methyl]-4-hydroxyacetanilide, followed by hydrolysis. Antimalarial activities of the new arylaminoquinoxalines were evaluated against the rodent malaria parasite Plasmodium yoelii at a dose of 75 mg kg-1. Three compounds synthesized (2-[3-[(diethylamino) methyl]-4-hydroxyanilino]-quinoxaline dihydrochloride (2b), 2-[3-[(pyrrolidinyl) methyl]-4-hydroxyanilino]-quinoxaline dihydrochloride (2f), and 2-[3-[(piperidinyl) methyl]-4-hydroxyanilino]-quinoxaline dihydrochloride (2g)) showed moderate antimalarial activity.

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