Category: 62163-09-1

Perkampus, H. H. published an article in 1962, the title of the article was Ultraviolet absorption spectra of some simple quinoxaline derivatives.Synthetic Route of 62163-09-1 And the article contains the following content:

The UV spectra of the following quinoxaline derivatives were investigated in different solvents: 2-Me-, 2-Cl-, 2-MeO-. 2,3-di-Me-, 2,3-di-MeO-, 2,3-di-isopropoxy-, 2,3-di-Cl-, 2,3-di-Br-, 5- and 6-Me, 5- and 6-Cl, and 6,7-di-Me. Position, intensity, and assignment of the absorption bands and the fine structure of the 1Lb band are tabulated. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

5-Chloroquinoxaline(cas:62163-09-1) belongs to quinoxaline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands. Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Landquist, Justus K. published an article in 1953, the title of the article was Quinoxaline N-oxides. I. The oxidation of quinoxaline and its Bz-substituted derivatives.Application of 62163-09-1 And the article contains the following content:

Quinoxaline (I) and its Bz-substituted-alkyl, alkoxy, halo, and acylamino derivatives are oxidized to 1- and 1,4-dioxides by organic peroxy acids. Resistance to N-oxidation is encountered in 5- and 8-substituted I. Reduction of 2,3-(O2N)2C6H3OEt with H and Raney Ni gave 3,1,2-EtOC6H3(NH2)2, oil (picrate, m. 210-12°). 2,4-Br(O2N)C6H3Me nitrated with HNO3 and H2SO4 at 40-5° gave 2,4,5-Br(O2N)2C6H2Me, m. 94-5°, which, treated with NH3 in alc. 5 h. at 120° and then reduced with Zn dust and NaOH in EtOH, yielded the 4,5-(H2N)2 analog, m. 140-1°. The following general procedure for preparation of I derivatives was used: (CHO.NaHSO3)2, an ο-phenylenediamine, and H2O were stirred 3 h. at 60°, then made alk. with KOH, and the I derivative was filtered off. The following derivatives were prepared (substituent, m.p., m.p. of 1-oxide, m.p. of 1,4-dioxide): 5-Me, 20-1°, b15, 120°, 131-2°, 192-4°; 5-EtO, 63-4°, b18 165-6°, 114-16°, -; 5-Cl (II), 60-2°, 177-9°, -; 6-iodo, 114-15°, -, -; 6-NC (III), 176-8°, -, -; 6,7-Me2, 100-1°, -, 220°; 6,7-benzo, 125-6°, -, -; 6,7-ClMe (IV), 120-2°, 166-8°, 227°; 6,7-BrMe (V), 127-8°, 167-8°, 222-4°; 6,7-Cl2 (VI), 210°, -, 206-8°; 5,8-Cl2 (VII), 205-7°, -, -; 6-Br (VIII)(prepared by the Sandmeyer reaction from the 6-NH2 compound), 48-9°, b18 146-9°, -, 223-5°; 6-AcNH (prepared from the 6-NH2 compound with Ac2O), 196.5°, -, 245-7°; 5-AcNH, -, 175-8°, 230-2° (insufficient for anal.). The following N-oxides were also prepared (substituent, m.p. 1-oxide, m.p. 1,4-dioxide): 6-Me (IX), -, 218-19°; 5,6-benzo, 158-9°, 215-16°; 5,6:7,8-dibenzo, 243-4°, -; 5-MeO, -, 222°; 6-MeO, -, 227-8°; 6-EtO, -, 192-4°; 5,6-(MeO)2, 138-40°, 220-2°; 6,7-(MeO)2, -, 264-5°; 2-Cl, 150-2°, -; 6-Cl (X), 151-2°, 211-12°. I is oxidized with equimolar AcO2H to quinoxaline 1-oxide, m. 122-3° (XI) while excess peroxy acid yields quinoxaline 1,4-dioxide, m. 241-3° (XII). Simultaneous with N-oxide formation there were obtained 2,3-dihydroxyquinoxalines which are listed below: (substituent, % yield, m.p.): IX, 1, 112°; II, 30, 142-3°; X, 15-30, 144°; VIII, 28, 132°; VII, 65, 160-1°; VI, 43, 170-70.5°; IV, 10, 172-3°; V, 12-6, 160-1°; III, 50, -; 6-O2N, 60, 150°. XI and MeI in MeCN set aside in the dark 36 h., precipitated 1-methylquinoxalinium iodide 4-oxide, m. 188-9°. XI was added cautiously to POCl3, and the mixture boiled 15 min. after the reaction subsided, poured on ice, made alk. with KOH, extracted with Et2O, and concentrated to yield 2-chloroquinoxaline, m. 46-8°. Under similar conditions XII yielded 2,3-dichloroquinoxaline; 5-methylquinoxaline 1-oxide gave 2-chloro-5-methylquinoxaline, m. 95°; and 5,6-benzoquinoxaline 1-oxide yielded 2-chloro-5,6-benzoquinoxaline, m. 120.5°. 2-C10H7NHCH2CO2Et dissolved treated in EtOH with PhN2Cl yielded 1,2-Ph2NC10H6NHCH2CO2Et, m. 135-6°, hydrogenated with Raney Ni at 60° and 50 atm. to 1,2,3,4-tetrahydro-2-oxo-7,8-benzoquinoxaline (XIII), m. 197-8°. XIII with alk. H2O2 gave 2-hydroxy-7,8-benzoquinoxaline, isolated as the hydrate, m. 275-5.5°, which was converted with POCl3 into 2-chloro-7,8-benzoquinoxaline, m. 128-9°. N-(6-nitro-o-tolyl)glycine in EtOH hydrogenated over Raney Ni at 60° and 60 atm. yielded 1,2,3,4-tetrahydro-5-methyl-2-oxoquinoxaline, m. 177-80°, readily oxidized to 2-hydroxy-5-methylquinoxaline, m. 282-3°. 2-Chloro-7,8-benzoquinoxaline and piperidine refluxed 1.5 h. gave 2-piperidino-7,8-benzoquinoxaline, m. 101.5-2.5°. 2-Piperidino-5,6-benzoquinoxaline, m. 124-5°, was similarly prepared Cl slowly passed 1 h. into 5,6-benzoquinoxaline in glacial HOAc, and the solution filtered and diluted with H2O yielded, on purification, dichloro-5,6-benzoquinoxaline, m. 187-8°. Methylation of 2,3-dihydroxy-6-nitroquinoxaline with Me2SO4 gave 3-hydroxy-1-methyl-6(or 7)-nitro-2(1H)-quinoxalinone, m. 344°. 6(or 7)-Cyano-3-hydroxy-1-methyl-2(1H)-quinoxalinone, m. 353-4°, is similarly prepared The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Application of 62163-09-1

5-Chloroquinoxaline(cas:62163-09-1) belongs to quinoxaline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands. Application of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Cheeseman, G. W. H.; Katritzky, A. R.; Ridgewell, B. J. published an article in 1963, the title of the article was The infrared spectra of polycyclic heteroaromatic compounds. III. 2-, 5-, and 6-substituted quinoxalines.Product Details of 62163-09-1 And the article contains the following content:

The infrared spectra of quinoxaline, 9 of its 2-substituted, 5 of its 5-substituted, and 8 of its 6-substituted derivatives are recorded and discussed, with tentative assignments of characteristic bands to specific mol. vibration modes. Cf. CA 56, 1073g. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Product Details of 62163-09-1

5-Chloroquinoxaline(cas:62163-09-1) belongs to quinoxaline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands. Product Details of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Favini, Giorgio; Simonetta, Massimo published an article in 1960, the title of the article was Electronic transitions in the aromatic chlorazines. III. Absorption spectra of monochloro quinoxalines, phthalazines, quinazolines, and cinnolines.Synthetic Route of 62163-09-1 And the article contains the following content:

The absorption spectra of 2-, 5-, and 6-chloroquinoxalines (I, II, III), 2-, 4-, and 6-chloroquinazolines (IV, V, VI), 1-, 5-, and 6-chlorophthalazines (VII, VIII, IX), and 3-, and 4-cinnolines (X, XI) were measured in isoöctane and in MeOH between 220 and 450 mμ. Condensation of o-(H2N)2C6H4 and OC(CO2Et)2 and hydrolysis, decarboxylation of the 2-hydroxyquinoxaline-3-carboxylic acid and chlorination with POCl3 gave I, m. 46-7° (C5H12). Acetylation of o-ClC6H4NH2 and nitration with fuming HNO3, deacetylation of the crystalline 2,6-Cl-(O2N)C6H3NHAc with NaOH, reduction with SnCl2, and condensation of the reduction product with OHCCHO.(NaHSO3)2 yielded II, m. 61-2° (petr. ether). Similarly, com. 4,2-Cl(H2N)C6H3NH2 was transformed to III, m. 63-4° (petr. ether). Reduction of o-O2NC6H4CHO, condensation with urea, and chlorination of the 2-quinazolone with PCl3 and POCl3 gave IV, m. 108° (ligroine). HCONH2 condensed with o-H2NC6H4CO2H and the 4-quinazolone chlorinated with PCl5 and POCl3 successively yielded V, m. 99-100° (petr. ether). Nitration of 3-ClC6H4CHO and condensation with HCONH2 followed by reduction with Zn in AcOH gave VI, m. 145° (dilute alc.). Phthalide transformed through the Br derivative into o-OHCC6H4CO2H, condensed with N2H4.H2O to the phthalazone and chlorinated with POCl3 yielded VII, m. 110-11° (ligroine). Conversion of 3,4-Me2C6H3NH2 by the Sandmeyer reaction gave 10 g. 3,4-Me2C6H3Cl, converted through 3,4-(CHBr2)2C6H3Cl to 3,4-(OHC)2C6H3Cl and condensed with N2H4 to yield 0.4 g. IX, m. 132°. α-Tetrahydronaphthylamine (5 g.) converted according to Sandmeyer to α-chlorotetrahydronaphthalene and submitted to oxidative degradation, the isomeric mixture condensed with N2H4, the product chlorinated with POCl3 and the mixture of dichlorophthalazines (0.2 g.) treated with HI and P to eliminate the Cl of the heterocyclic ring gave a small amount of VIII. HCN added to o-O2NC6H4CHO and the nitrile saponified, the NO2 group reduced catalytically and the acid diazotized, reduced with SnCl2 and the 3-hydroxycinnoline chlorinated with POCl3 gave X, m. 90-1° (ligroine). MeCOPh nitrated and reduced with Sn and HCl, the o-H2NC6H4COMe diazotized and transformed into 4-hydroxycinnoline, treated successively with PCl5 and POCl3, and recrystallized from ligroine gave XI, m. 78-9°. The nature of the bands observed and the infuence exerted on the absorption maximum by introduction of an atom of Cl into the benzodiazine structure were discussed. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

5-Chloroquinoxaline(cas:62163-09-1) belongs to quinoxaline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands. Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Favini, Giorgio; Simonetta, Massimo published an article in 1960, the title of the article was Electronic transitions in the aromatic chlorazines. II. Application of the method of Pariser and Parr to the azines of the monochlorinated benzene series.Application In Synthesis of 5-Chloroquinoxaline And the article contains the following content:

cf. CA 55, 7033g. The semiempirical method of Pariser and Parr was applied to PhCl (I), 2-, 3-, and 4-chloropyridines (II, III, IV), 2-, 3-, and 4-chloropyrimidines (V, VI, VII), chloropyrazine (VIII), and 3-chloropyridazine (IX). Comparison between theoretical and exptl. findings was limited to the values of energy transitions and oscillator strengths for the 1st singlet-singlet π-π’ transition. Monocentric and bicentric Coulomb integrals were calculated and tabulated. E was calculated for βCCl -0.86 and -2.50 without configuration interaction and with interaction of 5 and 8 configurations and the tabulated values were compared with exptl. values of ΔE. Oscillator strengths were calculated and similarly compared. The theory confirmed in all instances the bathochromic effect on the absorption maximum of the π-π’ transition caused by the introduction of an atom of Cl into C6H6 or an azine and, moreover gave shifts of the correct order of magnitude as shown by the tabulation (compound, Δν theoretical and exptl. (cm.-1) given): I, -870, -1350; II, -860, -1850; III, -1370, -2300; IV, -1830, -990; V, -1090, -1900; VI, -1730, -1250; VII, -2800, -2820; VIII, -970, -1460; IX, -2410, -1860. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Application In Synthesis of 5-Chloroquinoxaline

5-Chloroquinoxaline(cas:62163-09-1) belongs to quinoxaline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands. Application In Synthesis of 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On November 30, 1983, Lewis, Susan J.; Mirrlees, Margaret S.; Taylor, Peter J. published an article.Synthetic Route of 62163-09-1 The title of the article was Rationalizations among heterocyclic partition coefficients. Part 2: The azines. And the article contained the following:

π-Values (partition substituent constants) of 246 azines are given and discussed in terms of Δπ, the difference in π-value from that expected for C6H6. It is shown that Δπ is close to zero for alkyl and most halogen groups, but for polar substituents capable of H bonding it may be as high as φ1.6. Except for peri-positions, these Δπ-values may be correlated by a set of equations specific for different types of substituent position and containing terms which sep. parameterize proton-donor and -acceptor ability. The rationale behind this treatment is justified in terms of the nature of the octanol-H2O partitioning process and the manner in which electronic effects are expected to operate, in this context and that of the individual mol. Other topics discussed include: reasons for deviations among “irregular” substituents; the special problems of peri-positions; multisubstitution; and some consequences of this anal. for other types of compound The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

The Article related to azine structure partition coefficient, lfer azine, Pharmacology: Structure-Activity and other aspects.Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On February 8, 2018, Lee, Hsueh-Yun; Nepali, Kunal; Huang, Fang-I.; Chang, Chih-Yi; Lai, Mei-Jung; Li, Yu-Hsuan; Huang, Hsiang-Ling; Yang, Chia-Ron; Liou, Jing-Ping published an article.Computed Properties of 62163-09-1 The title of the article was (N-Hydroxycarbonylbenzylamino)quinolines as Selective Histone Deacetylase 6 Inhibitors Suppress Growth of Multiple Myeloma in Vitro and in Vivo. And the article contained the following:

A series of bicyclic arylamino/heteroarylamino hydroxamic acids (7-31) have been examined as novel histone deacetylase 6 (HDAC6) inhibitors. One compound (13, N-hydroxy-4-((quinolin-8-ylamino)methyl)benzamide) exhibits remarkable inhibitory activity of HDAC6 with an IC50 value of 0.29 nM, which is 4000-43,000 times more selective over other HDAC isoforms. Compound 13 was shown to have antiproliferative activity against human multiple myeloma RPMI 8226, U266, and NCI-H929 cells with no effect on normal bone marrow cells. Compound 13, as a single drug, suppresses the growth of tumors by a %TGI factor of 60.4% in human multiple myeloma RPMI 8226 xenograft models and, in combination with bortezomib, shows significant in vivo antitumor activity (%TGI = 86.2%). Compound 13 also demonstrates good human hepatocytic stability and high permeability, without any effect on mutagenicity and cytotoxicity. Thus, compound 13 is a potent HDAC6 inhibitor that could be developed for the treatment of multiple myeloma in the future. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Computed Properties of 62163-09-1

The Article related to hydroxycarbonylbenzylaminoquinoline preparation histone deacetylase hdac6 inhibitor antitumor myeloma, Pharmacology: Structure-Activity and other aspects.Computed Properties of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On November 28, 2018, Boergel, Jonas; Tanwar, Lalita; Berger, Florian; Ritter, Tobias published an article.Recommanded Product: 62163-09-1 The title of the article was Late-Stage Aromatic C-H Oxygenation. And the article contained the following:

Synthetic methods for oxidative aromatic C-O bond formation are sparse, despite their demand in metabolite synthesis for drug discovery and development. We report a novel methodol. for late-stage C-O bond formation of arenes. The reaction proceeds with excellent functional group tolerance even for highly functionalized substrates. The resulting aryl mesylates provide access to potential human metabolites of pharmaceuticals, and may be used directly to install a C-F bond to block metabolic hotspots. A charge-transfer interaction between the reagent bis(methanesulfonyl) peroxide and the substrate arenes may be relevant for the chemoselective functionalization of arenes over other functional groups. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Recommanded Product: 62163-09-1

The Article related to late stage aromatic oxygenation bismethanesulfonyl peroxide, aryl mesylate preparation, General Organic Chemistry: Synthetic Methods and other aspects.Recommanded Product: 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On October 31, 1980, Hollstein, Ulrich; Krisov, Galen E. published an article.Category: quinoxaline The title of the article was Carbon-13 NMR studies on some 5-substituted quinoxalines. And the article contained the following:

The 11 quinoxalines I (R = NO2, NH2, CO2H, OMe, Me, OH, F, Cl, Br, I, CN) were prepared and their 13C NMR were recorded in (D3C)2SO and assigned. The observed chem. shifts agree with those calculated from C6H6 substituent parameters and are close to those of corresponding carbons in 1-substituted phenazines and naphthalenes, except for the quinoxaline C-4a and C-8a which, due to their proximity to N, are downfield relative to those of the naphthalenes. The spectrum of I (R = F) was recorded in a range of solvents: in each case there was a low 2J(CF) for C-4a and no C-F spin-spin splitting for the 3-bond coupling of C-8a. Linear relationships exist between the Q parameter of the substituent and the chem. shift of C-4a, -5, and -6 and between the chem. shift of C-8 and the Hammet σp parameter of the substituent. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Category: quinoxaline

The Article related to nmr carbon quinoxaline substituent effect, Physical Organic Chemistry: Spectral and Related Studies and other aspects.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

On December 20, 2012, Cao, Sheldon; Popovici-Muller, Janeta; Salituro, Francesco G.; Saunders, Jeffrey; Tan, Xuefei; Travins, Jeremy; Yan, Shunqi; Ye, Zhixiong published a patent.Reference of 5-Chloroquinoxaline The title of the patent was Pyridinyl-heterocycles as isocitrate dehydrogenase 1 inhibitors and their preparation, therapeutically active compositions and their methods of use. And the patent contained the following:

Provided are compounds of formula I. pharmaceutically acceptable salts thereof, use of those compounds for treating cancer and pharmaceutical compositions comprising those compounds Compounds of formula I wherein Y is NR5, NR5CH2, CH2NR5 and CHR5; m is 0, 1, 2 and 3; R1a and R1b are independently H, C1-4 alkyl, heterocyclyl, etc.; R2 is (un)substituted Ph, (un)substituted 3- to 7-membered cycloalkyl, C2-4 alkyl and CF3; each R3 is independently halo,C1-4 fluoroalkyl, Ph, heteroaryl, etc.; R4 is H, CN, halo, C1-4 alkoxy, etc.; R5 is alkanoyl, alkenoyl, sulfonyl, etc.; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by a multistep procedure (procedure given). All the invention compounds were evaluated for their IDH1 R132H inhibitory activity. From the assay, it was determined that compound II exhibited IC50 value in the range of > 1 μM and ≤ 5 μM. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Reference of 5-Chloroquinoxaline

The Article related to pyridinyl heterocycle preparation idh1 inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Diazepines and other aspects.Reference of 5-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider