Heterocyclic Building Blocks-quinoxaline

On November 1, 2013, Troian-Gautier, Ludovic; De Winter, Julien; Gerbaux, Pascal; Moucheron, Cecile published an article.Formula: C8H5ClN2 The title of the article was A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ3-Iodinane Compounds. And the article contained the following:

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 chem. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Formula: C8H5ClN2

The Article related to quinoxaline tetraazaphenanthrene hexaazatriphenylene hypervalent iodinane oxidation, quinoxalinedione derivative preparation trifluoroacetoxyiodobenzene, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On November 27, 2006, Leclerc, Jean-Philippe; Fagnou, Keith published an article.Application of 34413-35-9 The title of the article was Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides. And the article contained the following:

Pyrazine, pyridazine, and pyrimidine N-oxides are regioselectively arylated with aryl iodides, bromides, and chlorides in the presence of a palladium catalyst;. The resulting products can be deoxygenated in high yield or further functionalized by making use of the N-oxide functionality. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Application of 34413-35-9

The Article related to diazine oxide aryl halide cross coupling palladium, aryldiazine oxide preparation deoxygenation, aryl diazine preparation, palladium cross coupling catalyst, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Application of 34413-35-9

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nasielski, J.; Heilporn, S.; Nasielski-Hinkens, R.; Tinant, B.; Declercq, J. P. published an article in 1989, the title of the article was An unexpected ring-opening in the Reissert reaction on 2,3-diphenylquinoxaline N-oxide.SDS of cas: 62163-09-1 And the article contains the following content:

When quinoxaline-N-oxide is reacted with KCN and BzCl in H2O or MeOH; the products are 2-, 5- and 6-chloroquinoxaline and small amounts of 2-cyanoquinoxaline. Using three equivalent of Me3SiCN instead of KCN, and CH2Cl2 as the solvent, leads to a 72% yield of 2-cyanoquinoxaline. The reaction of Me3SiCN and BzCl with 2,3-diphenylquinoxaline-N-oxide leads to 2-Bz2NC6H4N:CPhCN (I). The structure of I is based on spectroscopic data and on an X-ray crystallog. anal. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).SDS of cas: 62163-09-1

The Article related to quinoxaline oxide reissert, phenylquinoxaline oxide reissert ring cleavage, crystal structure benzaliminobenzoylaniline, mol structure benzaliminobenzoylaniline, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.SDS of cas: 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On February 28, 2011, Guemues, Selcuk published an article.Synthetic Route of 62163-09-1 The title of the article was The aromaticity of substituted diazanaphthalenes. And the article contained the following:

Substituted (F, Cl, OH) diazanaphthalene derivatives were considered theor. to obtain information about their stabilities and aromaticities. The expected decrease of aromaticity of naphthalene itself by double aza substitution was compensated by substitution of one of the hydrogens of the system by an electroneg. atom. The position of the substituent is strongly effective on the aromaticity of the structure such that, the aromaticity is enhanced when the substituent is closer to the aza points. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

The Article related to aromaticity diazanaphthalene, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On August 31, 2000, Manoharan, Mariappan; De Proft, Frank; Geerlings, Paul published an article.Name: 5,6,7,8-Tetrahydroquinoxaline The title of the article was A computational study of aromaticity-controlled Diels-Alder reactions. And the article contained the following:

The prime role of aromaticity in Diels-Alder reactions is studied computationally by ab initio and DFT methods using various masked dienes and ethylene. The reactions under consideration yield both aromatic stabilized and destabilized products through a concerted transition state due to the effect of ring functions embedded in the diene framework. Computations reveal that the cycloadditions involving various quinodimethanes achieve a progressive aromaticity gain during the reaction by the influence of aromatic functionalization; therefore they are kinetically as well as thermodynamically much more favorable than the typical butadiene-ethylene reaction. A series of these reactions affirms that the degree of aromatization increases with decreasing barrier and increasing exothermicity of a reaction. In reactions of benzo[c]heterocycles, aromaticity is lost due to the reacting heterocycle, but is gained by the adjacent hexagon during the reaction course. A partly occurring aromatic stabilization process in these reactions seems to facilitate the cycloaddition, but the remaining aromatic destabilization decreases the reaction rate and energy as compared to quinodimethane reactions. In the reactions of polyaromatic hydrocarbons viz. styrene, anthracene and pentacene, only loss of aromaticity occurs by virtue of aromatic defunctionalization. The progress of aromatization as well as dearomatization is evidenced from the nucleus independent chem. shifts (NICS) values whereas the aromaticity of the transition state and product is quantified by magnetic susceptibility exaltation (MSE) calculations Calculations thus establish with both magnetic and energetic criteria that the aromatic stabilization process as well as the aromatic ring function of the masked diene accelerates the reaction to the maximum extent through an ‘early’ TS, but the aromatic destabilization deactivates the cycloaddition via a ‘late’ TS. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Name: 5,6,7,8-Tetrahydroquinoxaline

The Article related to dft diels alder aromatization magnetic susceptibility, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Name: 5,6,7,8-Tetrahydroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On November 17, 2000, Manoharan, Mariappan; De Proft, Frank; Geerlings, Paul published an article.Recommanded Product: 5,6,7,8-Tetrahydroquinoxaline The title of the article was Enhanced Aromaticity of the Transition Structures for the Diels-Alder Reactions of Quinodimethanes: Evidence from ab Initio and DFT Computations. And the article contained the following:

The Diels-Alder reactions of various quinodimethanes with ethylene are studied by means of ab initio MO and d. functional theory (DFT) to show the effect of aromaticity on the reaction path. The calculations reveal that these reactions are both kinetically and thermodynamically much more favored than the prototype butadiene-ethylene Diels-Alder reaction due to the aromatization process in the transition state (TS) and product. A progressive aromaticity gain is noticed during the reaction, and hence the partial π-delocalized peripheral diene ring function is coupled with the six-electron σ,π-delocalized cyclic unit resulting in an enhanced aromaticity of the TS. The magnetic criteria such as magnetic susceptibility exaltation and nucleus independent chem. shift provide definitive evidence for and fully support the aromatization process and the aromaticity of the TS. The extent of σ-π delocalization and the bond make-break at the TS are consistent with each other, and this is strongly influenced by the adjacent π-aromatization process. Moreover, the aromaticity trends in the resulting TSs and products parallel the activation and reaction energies; the extent of aromatization increases with increasing reaction rate and exothermicity. This confirms that aromaticity is the driving factor governing cycloadditions involving quinodimethanes. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Recommanded Product: 5,6,7,8-Tetrahydroquinoxaline

The Article related to aromaticity transition state diels alder quinodimethane ab initio dft, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Recommanded Product: 5,6,7,8-Tetrahydroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On November 17, 2000, Manoharan, Mariappan; De Proft, Frank; Geerlings, Paul published an article.Electric Literature of 34413-35-9 The title of the article was Enhanced Aromaticity of the Transition Structures for the Diels-Alder Reactions of Quinodimethanes: Evidence from ab Initio and DFT Computations. And the article contained the following:

The Diels-Alder reactions of various quinodimethanes with ethylene are studied by means of ab initio MO and d. functional theory (DFT) to show the effect of aromaticity on the reaction path. The calculations reveal that these reactions are both kinetically and thermodynamically much more favored than the prototype butadiene-ethylene Diels-Alder reaction due to the aromatization process in the transition state (TS) and product. A progressive aromaticity gain is noticed during the reaction, and hence the partial π-delocalized peripheral diene ring function is coupled with the six-electron σ,π-delocalized cyclic unit resulting in an enhanced aromaticity of the TS. The magnetic criteria such as magnetic susceptibility exaltation and nucleus independent chem. shift provide definitive evidence for and fully support the aromatization process and the aromaticity of the TS. The extent of σ-π delocalization and the bond make-break at the TS are consistent with each other, and this is strongly influenced by the adjacent π-aromatization process. Moreover, the aromaticity trends in the resulting TSs and products parallel the activation and reaction energies; the extent of aromatization increases with increasing reaction rate and exothermicity. This confirms that aromaticity is the driving factor governing cycloadditions involving quinodimethanes. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Electric Literature of 34413-35-9

The Article related to aromaticity transition state diels alder quinodimethane ab initio dft, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Electric Literature of 34413-35-9

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On May 31, 2010, Mohajeri, Afshan; Shahamirian, Mozhgan published an article.Name: 5-Chloroquinoxaline The title of the article was Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene. And the article contained the following:

A quant. study on local aromaticity has been performed on a series of mono- and di-substituted biheterocycles (quinoline, isoquinoline, quinoxaline, quinazoline). Three electronically based indexes (PDI, ATI, and FLU) have been employed to investigate the substituent effect on the π-electron delocalization in both heterocycle and benzenoid rings. Three typical substituents (Cl, OCH3, and CN) with different inductive and resonance power have been selected. Generally, substituent causes a reduction in aromaticity irresp. of whether it is electron attracting or electron donating. It is shown that the maximum aromaticity exhibits a similar trend of Cl > CN > OCH3 for all the studied rings. Moreover, it is found that the substituent situation with respect to the heteroatom has a significant influence on the aromaticity. It results from our study that in di-substituted derivatives, irresp. of whether the two substituents form a meta or para isomer, they preferably choose the position which leads to the maximum aromaticity character. Copyright © 2009 John Wiley & Sons, Ltd. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Name: 5-Chloroquinoxaline

The Article related to substituent effect local aromaticity substituted heterocyclic naphthalene analog, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.Name: 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Verbeek, J.; Berends, W.; Van Beek, H. C. A. published an article in 1976, the title of the article was Photochemical hydroxylation of quinoxalines.Category: quinoxaline And the article contains the following content:

Irradiation of quinoxaline (I) in acidic aqueous solution under anaerobic conditions gave 5-hydroxyquinoxaline (II) and the 1,4-dihydroquinoxaline radical cation (III). III was characterized by ESR spectroscopy. Under aerobic conditions II is the only irradiation product formed. The effect of substituents attached to the benzene nucleus of I is analyzed. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Category: quinoxaline

The Article related to photochem hydroxylation quinoxaline, esr dihydroquinoxaline radial cation, Physical Organic Chemistry: Photo- and Irradiation-Induced Reactions, Free Radical-Induced Reactions, Free Radical Reactions and other aspects.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On February 28, 1982, McNab, Hamish published an article.Application In Synthesis of 5-Chloroquinoxaline The title of the article was Carbon-13 nuclear magnetic resonance spectra of quinoxaline derivatives. And the article contained the following:

I (R = H, 5-Me, 5-Cl, 5-OMe, 6-Me; 5,6-Me2; R1 = H, 2-Me, 2-Cl, 2-OMe; 2,3-Me2) are prepared by the cyclocondensation of a phenylenediamine with an α-oxoaldehyde or an α,β-diketone; their 13C NMR are assigned by a first order anal. 2,3-(H2N)2C6H3Me was treated with OHCCHO and NaHSO3 in H2O to give I (R = 5-Me, R1 = H). The 13C-H coupling constants are reported for some I. Acceptable additivity of substituent effects is found within the quinoxaline series. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Application In Synthesis of 5-Chloroquinoxaline

The Article related to quinoxaline preparation carbon 13 nmr, glyoxal cyclocondensation aminotoluene, Physical Organic Chemistry: Resonance Spectra (Electron Spin, Nuclear Magnetic and Fourier Transform Nuclear Magnetic, Quadrupole, etc.) and other aspects.Application In Synthesis of 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider