Wang, Qing-Qing’s team published research in Organic Letters in 2017-10-20 | 23088-24-6

Organic Letters published new progress about Acylation, regioselective (Minisci, chemoselective, electrochem.). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, HPLC of Formula: 23088-24-6.

Wang, Qing-Qing; Xu, Kun; Jiang, Yang-Ye; Liu, Yong-Guo; Sun, Bao-Guo; Zeng, Cheng-Chu published the artcile< Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by NH4I>, HPLC of Formula: 23088-24-6, the main research area is acylpyrazine acylquinoxaline heteroaryl ketone preparation; chemoselective green Minisci acylation pyrazine quinoxaline ketoacid ammonium iodide; ammonium iodide mediator electrochem Minisci acylation pyrazine quinoxaline ketoacid; mechanism electrochem Minisci acylation pyrazine quinoxaline ketoacid.

Electron-deficient aromatic nitrogen heterocycles, particularly pyrazines and quinoxalines, underwent chemoselective and green electrochem. Minisci acylations with α-ketoacids such as pyruvic acid mediated by NH4I, LiClO4, and hexafluoroisopropanol in MeCN to give heteroaryl ketones such as 2-acetylquinoxaline in 18-65% yields. Cyclic voltammetry and control experiments were used to delineate the mechanism of the Minisci acylation; I2 formed in situ likely reacts with carboxylate anions to yield acyl hypoiodites which then undergo decarboxylation to acyl radicals.

Organic Letters published new progress about Acylation, regioselective (Minisci, chemoselective, electrochem.). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, HPLC of Formula: 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Zhang, Lixi’s team published research in Molecular Catalysis in 2022-02-28 | 89898-96-4

Molecular Catalysis published new progress about Dicarboxylic acids, esters Role: RCT (Reactant), RACT (Reactant or Reagent). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Application In Synthesis of 89898-96-4.

Zhang, Lixi; He, Jingwen; Zhang, Pengfei; Zheng, Kai; Shen, Chao published the artcile< Visible-light-induced decarboxylative alkylation of quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates by cerium photocatalysis>, Application In Synthesis of 89898-96-4, the main research area is alkyl quinoxalinone preparation; quinoxalinone phenyliodine dicarboxylate visible light induced alkylation cerium photocatalyst.

3-Alkylquinoxalin-2(1H)-ones I [R1 = H, 6-Me, 7-Cl, etc.; R2 = Me, Et, Pr, propargyl, allyl, Bn; R3 = Me, Et, cyclopropyl, etc.] were prepered via visible-light-induced decarboxylative alkylation of quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylate using inexpensive CeCl3 as photocatalyst. Novel protocol had advantages of mild conditions, high yields and good substrate scope. Control experiments indicated that radical mechanism was responsible for the present transformation.

Molecular Catalysis published new progress about Dicarboxylic acids, esters Role: RCT (Reactant), RACT (Reactant or Reagent). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Application In Synthesis of 89898-96-4.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Carrer, Amandine’s team published research in Organic Letters in 2013-11-01 | 89898-96-4

Organic Letters published new progress about Arylation (oxidative). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Recommanded Product: 7-Nitro-2(1H)-quinoxalinone.

Carrer, Amandine; Brion, Jean-Daniel; Messaoudi, Samir; Alami, Mouad published the artcile< Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)ones with Arylboronic Acids>, Recommanded Product: 7-Nitro-2(1H)-quinoxalinone, the main research area is palladium catalyst oxidative arylation quinoxalinone arylboronic acid.

A straightforward palladium-catalyzed oxidative C-3 arylation of quinoxalin-2(1H)-ones with arylboronic acids is reported. E.g., in presence of Pd(OAc)2 as catalyst and 1,10-phenanthroline as ligand and O2 as oxidant, arylation of 1-methylquinoxalin-2(1H)-one with 4-MeOC6H4B(OH)2 gave 94% I. This protocol is compatible with a wide range of functional groups and allows construction of various biol. important quinoxalin-2(1H)-one backbones.

Organic Letters published new progress about Arylation (oxidative). 89898-96-4 belongs to class quinoxaline, and the molecular formula is C8H5N3O3, Recommanded Product: 7-Nitro-2(1H)-quinoxalinone.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Marques-Gallego, Patricia’s team published research in Dalton Transactions in 2010-06-07 | 5182-90-1

Dalton Transactions published new progress about Antitumor agents. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Computed Properties of 5182-90-1.

Marques-Gallego, Patricia; Gamiz-Gonzalez, M. Amparo; Fortea-Perez, Francisco R.; Lutz, Martin; Spek, Anthony L.; Pevec, Andrej; Kozlevcar, Bojan; Reedijk, Jan published the artcile< Quinoxaline-2-carboxamide as a carrier ligand in two new platinum(II) compounds: Synthesis, crystal structure, cytotoxic activity and DNA interaction>, Computed Properties of 5182-90-1, the main research area is crystal structure platinum quinoxalinecarboxamide chloro solvent complex; platinum quinoxalinecarboxamide chloro solvent preparation DNA binding unwinding cytotoxicity; ethylguanine substitution platinum quinoxalinecarboxamide chloro solvent DNA model; antitumor platinum quinoxalinecarboxamide chloro solvent complex.

The search for platinum compounds structurally different from cisplatin has led to two new platinum(II) compounds containing quinoxaline-2-carboxamide as a carrier ligand, i.e. cis-[Pt(qnxca)(MeCN)Cl2] (1) and the [Pt(qnxca-H)(DMSO)Cl] (2). Both compounds have been synthesized and characterized using different spectroscopic methods. In addition, single-crystal structures have been determined by X-Ray diffraction for both compounds In each case a square planar Pt(II) is present; in (1) the qnxca is monodentate and neutral, whereas in (2) the ligand has lost a hydrogen, to form the anionic chelating ligand abbreviated as qnxca-H. The biol. activity of both compounds has been investigated in a panel of seven human tumor cells, displaying poor cytotoxic activity, compared to cisplatin. The interaction of the new compounds with 1 or 2 equivalent of 9-ethylguanine has been studied using 1H NMR, 195Pt NMR and ESI-MS spectroscopy, finding poor reactivity of 1 towards the model base, forming only the monosubstituted adduct. Surprisingly, compound 2, which is more sterically crowded, interacts more efficiently with the 9-EtG, forming a bifunctional adduct with two 9-EtG with substitution of the DMSO and the chloride ligand. Unwinding studies of pUC19 plasmid DNA by compound 1 show similar unwinding properties to cisplatin.

Dalton Transactions published new progress about Antitumor agents. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Computed Properties of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Rao, Koppaka V’s team published research in Journal of Heterocyclic Chemistry in 1973 | 23088-24-6

Journal of Heterocyclic Chemistry published new progress about Reduction. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Related Products of 23088-24-6.

Rao, Koppaka V.; Jackman, Dennis published the artcile< Reaction of sodium borohydride with heteroaromatic nitro compounds>, Related Products of 23088-24-6, the main research area is quinoxaline nitro reduction; quinoline nitro reduction; tetrahydronitroquinoxaline; dihydronitroquinoline.

Quinoxalines (I, R = 5-, 6-NO2, 6-CN, 6-CO2Et, 6-CF3) and 5-, 6-, 7-, 8-nitroquinoline (II) were reduced selectively by NaBH4 in HOAc at 5° to give 1,2,3,4-tetrahydro-derivatives of I and 1,2-dihydro-derivatives of II resp. 5-Nitroisoquinoline was reduced to the 1,2,3,4-tetrahydro derivative in HOAc at 5° but yielded the 1,2-dihydro derivative in aqueous MeOH.

Journal of Heterocyclic Chemistry published new progress about Reduction. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Related Products of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Huang, Yao’s team published research in Organic & Biomolecular Chemistry in 2015 | 5182-90-1

Organic & Biomolecular Chemistry published new progress about Amidation. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Reference of 5182-90-1.

Huang, Yao; Chen, Tieqiao; Li, Qiang; Zhou, Yongbo; Yin, Shuang-Feng published the artcile< Copper catalysed direct amidation of methyl groups with N-H bonds>, Reference of 5182-90-1, the main research area is methyl group amidation copper catalyst.

An efficient copper catalyzed direct aerobic oxidative amidation of Me groups of azaarylmethanes with N-H bonds producing amides is successfully developed, which can produce primary, secondary and tertiary amides, including those with functional groups. This reaction represents a straightforward method for the preparation of amides from the readily available hydrocarbon starting materials.

Organic & Biomolecular Chemistry published new progress about Amidation. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Reference of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Lewis, Susan J’s team published research in Quantitative Structure-Activity Relationships in 1983-11-30 | 5182-90-1

Quantitative Structure-Activity Relationships published new progress about Molecular structure-property relationship, partition. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, SDS of cas: 5182-90-1.

Lewis, Susan J.; Mirrlees, Margaret S.; Taylor, Peter J. published the artcile< Rationalizations among heterocyclic partition coefficients. Part 2: The azines>, SDS of cas: 5182-90-1, the main research area is azine structure partition coefficient; LFER azine.

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

Quantitative Structure-Activity Relationships published new progress about Molecular structure-property relationship, partition. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, SDS of cas: 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Tymoshenko, D O’s team published research in Science of Synthesis, Knowledge Updates in 2012 | 5182-90-1

Science of Synthesis, Knowledge Updates published new progress about Organic synthesis. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Electric Literature of 5182-90-1.

Tymoshenko, D. O. published the artcile< Quinoxalines (update 2012)>, Electric Literature of 5182-90-1, the main research area is review quinoxaline preparation.

A review of the synthetic approaches to quinoxaline and related systems.

Science of Synthesis, Knowledge Updates published new progress about Organic synthesis. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Electric Literature of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Landquist, Justus K’s team published research in Journal of the Chemical Society in 1953 | 23088-24-6

Journal of the Chemical Society published new progress about Oxidation. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Recommanded Product: 6-Quinoxalinecarbonitrile.

Landquist, Justus K. published the artcile< Quinoxaline N-oxides. I. The oxidation of quinoxaline and its Bz-substituted derivatives>, Recommanded Product: 6-Quinoxalinecarbonitrile, the main research area is .

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

Journal of the Chemical Society published new progress about Oxidation. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Recommanded Product: 6-Quinoxalinecarbonitrile.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

 

Otsuka, H’s team published research in Tetrahedron in 1965 | 5182-90-1

Tetrahedron published new progress about 5182-90-1. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Reference of 5182-90-1.

Otsuka, H.; Shoji, J. published the artcile< Structure of triostin C>, Reference of 5182-90-1, the main research area is .

Triostin antibiotics from a streptomyces related to Streptomyces aureus gave a mixture of components C and A. The mixture (600 mg.) chromatographed on silica gel and eluted with CHCl3-MeOH solutions containing increased concentrations of MeOH from 0-3% and with control by observation of optical densities at 243 mμ, the antibiotic fractions examined by thin-layer chromatography on Al2O3 (solvent, lower layer of 3:1:3 EtOAcCl2CHCHCl2-H2O) and the concentrates containing component C crystallized from CHCl3-MeOH gave 280 mg. triostin C (I), decomposing above 260°, [α]24D -143.9 ± 2° (c 1.121, CHCl3), mol. weight 1125 (Barger-Niederl, CHCl3), 1120 (osmometry, CHCl3). I hydrolyzed 20 hrs. in 6N HCl at 105° and the hydrolysate examined by 2-dimensional paper chromatography gave 4 ninhydrin pos. substances, Rf in 4:1:2 BuOH-AcOH-H2O (and H2O-saturated PhOH): N,N’-dimethylcycstine (II) 0.18 (0.84); alanine (III) 0.36 (0.56); N,γ-dimethylalloisoleucine (IV) 0.74 (0.92); serine (V) 0.26 (0.37). When developed with a collidine-containing MeOH ninhydrin solution (CA 59, 9550a) the spots were brownish-purple, purple, brownish-purple, and grayish-purple. II and IV gave red spots with p-O2NC6H4COCl-C5H5N, indicative of N-alkyl amino acids, and II gave also a red spot with Na2Fe(CN)5NO.2H2O-NaCN. The total acid hydrolysate from 500 mg. I concentrated and extracted with H2O, chromatographed on cellulose and eluted with 4:1:2 BuOH-AcOH-H2O gave in order IV, III, V, II. Similar chromatographic separation on Dowex 50 W × 4 and elution with 0.2M C5H5N-HCO2H (pH 2.80) gave II, V, IV and III in order with partial overlap. The individual acids were isolated by decolorization of the fractions with C and recrystallization to give V, m. 220-5° (decomposition) (H2O-EtOH), [α]24D -14.6 ± 2° (c 0.994, 1.0N HCl); L-III, m. 280-2° (decomposition) (H2O-EtOH), [α]23D 12.1 ± 4° (c 0.626, 1.0N HCl); II, gel-like and difficult to purify, m. 175-82° (decomposition), [α]26D 22.7 ± 2° (c 1.049, 1.0N HCl), [α]25D 34.0 ± 2° (c 1.022, 1.0N HCl), ir spectrum identical with that of synthetic compound, m. 215-17° (decomposition), [α]25D 58.1 ± 2° (c 1.00, 1.0N HCl); L-IV, m. 300°, [α]25.5D 28.4 ± 2° (c 0.937, H2O), 41.9 ± 2° (c 1.049, 5N HCl). II (10 mg.) in 2 ml. H2O stirred 2 hrs. at 45° with 300 mg. Raney Ni and the combined filtrate and H2O-washings examined by paper chromatography on 4:1:2 BuOH-AcOH-H2O, H2O-saturated iso-Pr CH2OH, H2O-saturated Me2CCH2OH, H2O-saturated PhCH2OH, and H2O-saturated PhOH showed Rf values of 0.40, 0.22, 0.06, 0.15, and 0.84 resp., identical with those of synthetic DL-MeCH(NHMe)CO2H. I (500 mg.) partially hydrolyzed in concentrated HCl at 37° 2 days and extracted with EtOAc, the aqueous layer examined for amino acids and the decolorized extract chromatographed on paper with BuOH saturated with 3% aqueous NH4OH as solvent gave quinoxaline-2-carboxylic acid (VI), m. 210-11° (decomposition), ir spectrum identical with that of synthetic VI. I (4.100 mg.) in 0.5 ml. 6N HCl heated 72 hrs. at 105° in an evacuated sealed tube and the hydrolysate submitted to amino acid analysis showed the presence per mole I of 1.48 moles V, 2.02 moles III, 2.16 moles half II, and 2.14 moles IV. A larger amount of V was obtained under milder conditions of hydrolysis. I (2.160 mg.) heated 20 hrs. in 0.3 ml. 5N NaOH at 105° and adjusted with Dowex 50 W (H type) to pH 8.2, acidified with dilute HCl and analyzed gave 0.083 moles V, 1.98 moles III, 1.67 moles IV, and 0.74 mole NH3 per mole I. Extraction of a portion of the hydrolysate with EtOAc gave VI. I (100 mg.) in 6 ml. 90% MeOH containing 0.1N Na0H stirred 2 hrs. at 25° and diluted with 40 ml. H2O, adjusted to pH 2.0 and extracted with EtOAc, transferred into 15 ml. 5% NaHCO3 and reextracted with EtOAc at pH 2.0, the washed extract concentrated and diluted with C6H14 gave 93 mg. alkali-treated triostin C (VII), m. 159-62°, mol. weight 1300 (osmometry, CHCl3), 1000-1300 (Barger-Akiya, Me2CO), pKa 5.7, giving only 0.065 mole V, 1.98 moles III, 2.04 moles half II, 2.06 moles IV, and 2.32 moles NH3 in acid hydrolysis, suggesting the formation of a dehydroalanine derivative by β-elimination reaction on the O-substituted serine residue caused by alkali treatment. VII (15 mg.) heated 3 hrs. at 100° in 0.5 ml. 3N HCl gave 1.8 mole pyruvic acid as determined as its 2,4-dinitrophenylhydrazone, m. 218-20° (MeOH-H2O). VII in 1:1 dioxane-H2O boiled at pH 2.0 released quinoxaline-2-carboxamide, m. 204.5-5.5°. Dakin-West degradation of VII showed that IV was the C-terminal amino acid. VII dinitrophenylated and submitted to acid hydrolysis failed to give dinitrophenylated amino acids, indicating that VI was attached to N-terminal amino acid. Accordingly a lactone linkage was presumed to exist in I. CrO3 oxidation of I did not destroy V, indicating that the OH group of V was involved in the lactone linkage. I (100 mg.) in 2 ml. HCO2H kept 16 hrs. at 0° with 20 ml. performic acid reagent according to Thompson (CA 49, 4748a) and the mixture diluted with 80 ml. H2O, freeze-dried and the residue extracted with MeOH, precipitated with Et2O and the 80 mg. hygroscopic powder analyzed showed the presence of III, IV, V, and N-methylcysteic acid (VIII). I (100 mg.) in 15 ml. 4:1 dioxane-H2O stirred 4.5 hrs. with 1.0 g. Raney Ni W-2 at 80-90° and the filtered solution and washings evaporated, the residue extracted and the extract diluted with C6H14 gave 68 mg. dethiotriostin C (IX), m. 183-6° (decomposition), mol. weight 940, 1000-1300, hydrolyzed to give 1.48 moles V, 1.90 moles III, 2.00 moles N-methylalanine (X), and 1.99 moles IV. I gave no reaction with Na2Fe(CN)5NO-NaCN reagent but a pos. reaction for the disulfide bond was obtained following treatment with cold, dilute NaOH with opening of the lactone ring and increasing solubility The mol. weight determination of IX confirmed a proposed partial formulation and it remained to elucidate the amino acid sequence between IV and V. IX was partially hydrolyzed by concentrated HCl at 37° 2 days and the hydrolysate extracted with BuOH to sep. chromophore and simple peptide fragments. The chromophore peptides, characterized by uv absorption, were separated on a 2-dimensional paper chromatogram in BuOH saturated with aqueous NH4OH followed by 1.5M phosphate buffer, pH 5.0, giving N-(quinoxaline-2-carboxyl)serine and N-(quinoxaline-2-carboxyl)serylalanine, N-(quinoxaline-2-carboxyl)-O-(N,γ-dimethylalloisoleucyl)serine and N-(quinoxaline-2-carboxyl)-O-(N,γ-dimethylalloisoleucyl)serylalanine. As simple peptide fragments, serylalanine and serylalanyl-N-methylalanyl-N,γ-dimethylalloisoleucine were separated by paper chromatography in BuOH-AcOH-H2O followed by H2O-saturated phenol. Similar acid hydrolysis with I gave another 2 peptide fragments consisting of V, III and N,N’-dimethylcystine. It was concluded that I has the proposed structure. There are 2 series of quinoxaline antibiotics; one has a dithiane ring as in echinomycin, and the other contains an N,N’-dimethyl residue. Each series involves several antibiotics differing only in their N-methylamino acid constituents.

Tetrahedron published new progress about 5182-90-1. 5182-90-1 belongs to class quinoxaline, and the molecular formula is C9H7N3O, Reference of 5182-90-1.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider