Tag: 200-300

Structure-based design of novel quinoxaline-2-carboxylic acids and analogues as Pim-1 inhibitors was written by Oyallon, Bruno;Brachet-Botineau, Marie;Loge, Cedric;Bonnet, Pascal;Souab, Mohamed;Robert, Thomas;Ruchaud, Sandrine;Bach, Stephane;Berthelot, Pascal;Gouilleux, Fabrice;Viaud-Massuard, Marie-Claude;Denevault-Sabourin, Caroline. And the article was included in European Journal of Medicinal Chemistry in 2018.Formula: C11H9ClN2O2 This article mentions the following:

We identified a new series of quinoxaline-2-carboxylic acid derivatives, targeting the human proviral integration site for Moloney murine leukemia virus-1 (HsPim-1) kinase. Seventeen analogs were synthesized providing useful insight into structure-activity relationships studied. Docking studies realized in the ATP pocket of HsPim-1 are consistent with an unclassical binding mode of these inhibitors. The lead compound I was able to block HsPim-1 enzymic activity at nanomolar concentrations (IC₅₀ of 74 nM), with a good selectivity profile against a panel of mammalian protein kinases. In vitro studies on the human chronic myeloid leukemia cell line KU812 showed an antitumor activity at micromolar concentrations As a result, compound I represents a promising lead for the design of novel anticancer targeted therapies. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Formula: C11H9ClN2O2).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxaline-1,4-di-N-oxide derivatives have shown to improve the biological results and are endowed with anti-viral, anti-cancer, anti-bacterial, and anti-protozoal activities with application in many other therapeutic areas.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

N-Oxides of the quinoxaline series. I. N-Oxides of quinoxaline-2-carboxylic acid was written by Elina, A. S.;Magidson, O. Yu.. And the article was included in Zhurnal Obshchei Khimii in 1955.Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

2-(m-Nitrostyryl)quinoxaline (6.3 g.) heated to boiling in 200 ml. Me₂CO, cooled and treated with 5% aqueous KMnO₄, filtered (when colorless, the filtrate concentrated and acidified gave mixed acids which treated with 30 ml. 10% NaHCO₃ followed by 10 ml. EtOH gave Na quinoxaline-2-carboxylate, which with dilute HCl gave the free acid (I), m. 210-11°, in 56.4% yield; Et ester, m. 83-4°. To 20 g. 2-methylquinoxaline in MePh (240 ml.) was slowly added 18 g. SeO₂, the mixture refluxed 1.5 hrs., filtered, the filtrate steam distilled, and the distillate salted out gave quinoxaline-2-carboxaldehyde, which is extracted with Et₂O; the pure aldehyde, 56.6%, m. 110° (from petr. ether); the precipitate from the reaction yielded 19.8% I. The aldehyde with thiosemicarbazide in EtOH gave the thiosemicarbazone, decompose 238-9°. The aldehyde treated with KMnO₄ in Me₂CO gave 72.7% I. I Et ester (4.75 g.) added over 3 hrs. at 45° to 25 ml. AcOH, 19.2 ml. Ac₂O, and 23 ml. 30% H₂O₂ and kept 16 hrs. at 50° gave on neutralization with NaHCO₃, 80.1% yellow I 4-oxide Et ester (II), m. 156-7° (from MeOH); similar treatment of I gave I 4-oxide, 80%, m. 180-2° (from EtOH), this substance also being formed in good yield on stirring its Et ester 20 min. with 7.5% NaOH. II and alc. NH₃ kept 12 hrs. at room temperature gave I 4-oxide amide, m. 230-30.5° (from EtOH). II in EtOH with 85% N₂H₄ after 12 hrs. at room temperature gave 90% I 4-oxide hydrazide, m. 216-17° (from 50% EtOH). NH₂OH.HCl (1.64 g.) in 9 ml. MeOH treated with 1.97 g. KOH in 29 ml. MeOH, followed, at 40°, by 2 g. II and kept 20 hrs. gave K quinoxaline-2-hydroxamate 4-oxide, yellowish, m. 185-6° (from H₂O). To I 4-oxide (0.3 g.) in 3.5 ml. 15% NaOH and 22 ml. H₂O was slowly added 0.5 g. Na₂S₂O₄ and after 1 hr. at room temperature the mixture was acidified to Congo red, yielding 83.9% I. II (1 g.) and 10 ml. POCl₃ refluxed 1.5 hrs., concentrated, quenched in ice and neutralized, gave Et 3-chloroquinoxaline-2-carboxylate, m. 41.5-2° (cf. Gowenlock, et al., C.A. 40, 341.3), which heated 1.5 hrs. with Na₂CO₃ in 70% MeOH gave the corresponding free acid, m. 146-7° (decomposition); passage of NH₃ in EtOH solution of the Et ester at 0° gave 3-chloroquinoxaline-2-carboxamide, m. 214-15°. To 3 g. 2-methylquinoxaline 1,4-dioxide in C₆H₆ at reflux was added 3.5 g. SeO₂ and after 2 hrs. refluxing, the filtrate yielded 2.02 g. quinoxaline-2-carboxaldehyde 1,4-dioxide, decompose 189-90°, which gives typical aldehyde reactions and liberates iodine from acidic KI solution This on oxidation with 30% H₂O₂ in AcOH-Ac₂O at 50° 1 hr. gave I 1,4-dioxide, yellow, m. 208-9° (from AcOH); this reduced with Na₂S₂O₄ in 5% NaOH at 20-5° to I 1-oxide, colorless, m. 180-1°; this reduced with Na₂S₂O₄ in 3% NaOH to I. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

QCM-4 a novel 5-HT₃ antagonist attenuates the behavioral and biochemical alterations on chronic unpredictable mild stress model of depression in Swiss albino mice was written by Kurhe, Yeshwant;Radhakrishnan, Mahesh;Gupta, Deepali;Devadoss, Thangaraj. And the article was included in Journal of Pharmacy and Pharmacology in 2014.Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

Objectives: The inconsistent therapeutic outcome necessitates identifying novel compounds for the treatment of depression. Therefore, the present study is aimed at evaluating the antidepressant-like effects of a novel 5-HT₃ receptor antagonist 3-methoxy-N-p-tolylquinoxalin-2-carboxamide (QCM-4) on chronic unpredictable mild stress (CUMS) induced behavioral and biochem. alterations in mice. Methods: Animals were subjected to different stressors for a period of 28 days. Thereafter, battery tests like locomotor score, sucrose preference test, forced swim test (FST), tail suspension test (TST), elevated plus maze (EPM) and open field test (OFT) were performed. Biochem. assays like lipid peroxidation, nitrite levels, reduced glutathione (GSH), catalase and superoxide dismutase (SOD) were assessed in brain homogenate. Key findings: QCM-4 dose dependently reversed the CUMS induced behavioral and biochem. alterations by increasing the sucrose consumption, reducing the immobility time in FST and TST, increasing the percent time in open arm in EPM and increasing the ambulation along with the rearings and decreased number of fecal pellets in OFT. Further, biochem. alterations were attenuated by QCM-4 as indicated by reduced lipid peroxidation and nitrite levels and elevated antioxidant enzyme levels like GSH, catalase and SOD. Conclusions: QCM-4 attenuated the behavioral and biochem. derangements induced by CUMS in mice, indicating antidepressant behavior of the novel compound In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

1-Alkyl-4-oxo-1,4-dihydropyrido[2,3-b]quinoxaline-3-carboxylic acids with antibacterial action was written by Pesson, Marcel;De Lajudie, Pierre;Antoine, Michel;Chabassier, Simone;Girard, Philippe. And the article was included in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques in 1976.SDS of cas: 49679-45-0 This article mentions the following:

Pyridoquinoxalinecarboxylic acids I (R = H; R1 = Me, Et; R2 = H, Me, Cl, OMe; R3 = H, Me, OMe) were prepared by treating the quinoxalines II (R = Me, Et, R4 = Cl) with R1NHCH2CH2CO2H, esterifying II (R4 = NR1CH2CH2CO2H), cyclizing II (R4 = NR1CH2CH2CO2R), brominating-dehydrobrominating the dihydro derivatives of I (R = Me, Et), and saponifying I (R = Me, Et). I have bactericidal activity, which is reduced by substitution in the 7- or 8-positions. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0SDS of cas: 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.SDS of cas: 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

N-Oxides of the quinoxaline series. I. N-Oxides of quinoxaline-2-carboxylic acid was written by Elina, A. S.;Magidson, O. Yu.. And the article was included in Zhurnal Obshchei Khimii in 1955.Name: Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

2-(m-Nitrostyryl)quinoxaline (6.3 g.) heated to boiling in 200 ml. Me₂CO, cooled and treated with 5% aqueous KMnO₄, filtered (when colorless, the filtrate concentrated and acidified gave mixed acids which treated with 30 ml. 10% NaHCO₃ followed by 10 ml. EtOH gave Na quinoxaline-2-carboxylate, which with dilute HCl gave the free acid (I), m. 210-11°, in 56.4% yield; Et ester, m. 83-4°. To 20 g. 2-methylquinoxaline in MePh (240 ml.) was slowly added 18 g. SeO₂, the mixture refluxed 1.5 hrs., filtered, the filtrate steam distilled, and the distillate salted out gave quinoxaline-2-carboxaldehyde, which is extracted with Et₂O; the pure aldehyde, 56.6%, m. 110° (from petr. ether); the precipitate from the reaction yielded 19.8% I. The aldehyde with thiosemicarbazide in EtOH gave the thiosemicarbazone, decompose 238-9°. The aldehyde treated with KMnO₄ in Me₂CO gave 72.7% I. I Et ester (4.75 g.) added over 3 hrs. at 45° to 25 ml. AcOH, 19.2 ml. Ac₂O, and 23 ml. 30% H₂O₂ and kept 16 hrs. at 50° gave on neutralization with NaHCO₃, 80.1% yellow I 4-oxide Et ester (II), m. 156-7° (from MeOH); similar treatment of I gave I 4-oxide, 80%, m. 180-2° (from EtOH), this substance also being formed in good yield on stirring its Et ester 20 min. with 7.5% NaOH. II and alc. NH₃ kept 12 hrs. at room temperature gave I 4-oxide amide, m. 230-30.5° (from EtOH). II in EtOH with 85% N₂H₄ after 12 hrs. at room temperature gave 90% I 4-oxide hydrazide, m. 216-17° (from 50% EtOH). NH₂OH.HCl (1.64 g.) in 9 ml. MeOH treated with 1.97 g. KOH in 29 ml. MeOH, followed, at 40°, by 2 g. II and kept 20 hrs. gave K quinoxaline-2-hydroxamate 4-oxide, yellowish, m. 185-6° (from H₂O). To I 4-oxide (0.3 g.) in 3.5 ml. 15% NaOH and 22 ml. H₂O was slowly added 0.5 g. Na₂S₂O₄ and after 1 hr. at room temperature the mixture was acidified to Congo red, yielding 83.9% I. II (1 g.) and 10 ml. POCl₃ refluxed 1.5 hrs., concentrated, quenched in ice and neutralized, gave Et 3-chloroquinoxaline-2-carboxylate, m. 41.5-2° (cf. Gowenlock, et al., C.A. 40, 341.3), which heated 1.5 hrs. with Na₂CO₃ in 70% MeOH gave the corresponding free acid, m. 146-7° (decomposition); passage of NH₃ in EtOH solution of the Et ester at 0° gave 3-chloroquinoxaline-2-carboxamide, m. 214-15°. To 3 g. 2-methylquinoxaline 1,4-dioxide in C₆H₆ at reflux was added 3.5 g. SeO₂ and after 2 hrs. refluxing, the filtrate yielded 2.02 g. quinoxaline-2-carboxaldehyde 1,4-dioxide, decompose 189-90°, which gives typical aldehyde reactions and liberates iodine from acidic KI solution This on oxidation with 30% H₂O₂ in AcOH-Ac₂O at 50° 1 hr. gave I 1,4-dioxide, yellow, m. 208-9° (from AcOH); this reduced with Na₂S₂O₄ in 5% NaOH at 20-5° to I 1-oxide, colorless, m. 180-1°; this reduced with Na₂S₂O₄ in 3% NaOH to I. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Name: Ethyl 3-chloroquinoxaline-2-carboxylate).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB),One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene.Name: Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis and pharmacology of some new 2-arylamino-4-oxo[1,3]thiazino[5,6-b]quinoxalines was written by Bansal, O. P.;Srinivas, J. S.;Singh, P. P.;Junnarkar, A. Y.. And the article was included in Indian Journal of Chemistry in 1993.Recommanded Product: Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

Several new 2-arylamino-4-oxo[1,3]thiazino[5,6-b]quinoxalines I (R = Ph, substituted phenyl) were prepared by treating Et 2-chloroquinoxaline-3-carboxylate with various arylthioureas. The compounds possess CNS depressant activity. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Recommanded Product: Ethyl 3-chloroquinoxaline-2-carboxylate).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.Recommanded Product: Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quinoxaline derivatives. V. Some reactions of 2-cyano-3-hydroxyquinoxaline 1-oxide was written by Ahmad, Yusuf;Habib, M. S.;Iqbal, M.;Ziauddin. And the article was included in Bulletin of the Chemical Society of Japan in 1965.SDS of cas: 1910-90-3 This article mentions the following:

As has been reported the title compound (I, R = H), with a CN group and a N-oxide side by side, has unusual properties (Pachter and Kloetzel, CA 47, 10542b) and was unchanged on refluxing with PCl₃. Deoxygenation by reduction with Na dithionate in HOAc or EtOH, Zn and HCl, or catalytically with H over Pd-C was accompanied by loss of the CN group and gave in each case II (R = R¹ = R² = H). I refluxed with PhNH₂ 4 hrs., cooled, and diluted with petr. ether gave 90% II (R = R¹ = H, R² = NHPh), m. 247-8° (EtOH). Similarly with excess MeNHPh, I (R = H) gave 40% II (R = R¹ = H, R² = NMePh), m. 180-2° (EtOH), which was refluxed with Me₂SO₄ in the presence of anhydrous K₂CO₃ and Me₂CO to give 50% II (R = H, R¹ = Me, R² = NMePh), m. 145-6°, the ir spectrum and mixed m.p. of which were identical with a sample prepared by the method of Clark-Lewis (CA 51, 10537g). Similarly, I (R = H) with cyclohexylamine gave 90% II (R = R¹ = H, R² = cyclohexylamino), m. 246° (EtOH). I (R = Cl) or I (R = EtO) with PhNH₂ gave in good yield II (R = Cl, R¹ = H, R² = NHPh), m. 318-19° (glacial HOAc), or II (R = EtO, R¹ = H, R² = NHPh), m. 260-1° (EtOH), resp. I (R = H) or III refluxed in fuming HBr 2 hrs. and the mixture cooled and diluted with H₂O gave 30% IV (R = R¹ = H), m. >350° (HCONMe₂-EtOH). By this treatment, I (R = H) with Ph in place of CN, was deoxygenated quant. to II (R = R¹ = H, R² = Ph) (unpublished work). Ir spectra of IV (R = R¹ = H) and an authentic sample prepared by the method of Curd, et al. (CA 44, 3501e) were identical. The following sequence is suggested for this reaction: I(R = H ) → III → III(with CO₂H in place of CONH₂) which by decarboxylation gave 3-hydroxyquinoxaline 1-oxide, which by rearrangement gave 2,3-dihydroxyquinoxaline (loc. cit.), then bromination by Br formed by the action of part of the N-oxide on HBr or by aerial oxidation of HBr. In contrast, I (R = H) was unchanged by refluxing 8 hrs. with a 1:1 mixture of concentrated HCl and HOAc, or by heating under reflux with AcCl in a sealed tube at 100° 72 hrs. III, heated with a 1:1 mixture of HCl and HOAc, gave 2,3-dihydroxyquinoxaline. A mixture of this with fuming HBr refluxed 8 hrs. gave 20% monobromo derivative, m. >350° (HCONMe₂-EtOH), which was identical in ir spectrum with IV (R = R¹ = H) prepared from I (R = H) or III. Also the addition of a calculated amount aqueous KBrO₃ to a solution of 2,3-dihydroxyquinoxaline in hot, fuming HBr precipitated at once a quant. yield of monobromo derivative, m. >350° (HCONMe₂-EtOH), identical in ir spectrum with IV (R = R¹ = H) prepared from I (R = H) or III. Either of these monobromo derivatives refluxed 3 hrs. with anhydrous K₂CO₃ and Me₂SO₄ in Me₂CO, the mixture filtered, and the filtrate concentrated gave a good yield of IV (R = R¹ = Me), m 205-6° (EtOH), the ir spectrum and mixed m.p. of which were identical with a sample prepared by the methylation of IV (R = Me, R¹ = H) with Me2₂SO₄ and aqueous NaOH. Curd, et al. (loc. cit.) recorded its m.p. as 205-6°. Hydrogenation of 4-bromo-2-methylamino-1-nitrobenzene in EtOH over Pd-C gave 4-bromo-2-methylaminoaniline, which, refluxed in EtOH solution with Et oxalate 3.5 hrs. gave IV (R = Me, R¹ = H), m. 325-7° (HOAc). In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3SDS of cas: 1910-90-3).

6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.SDS of cas: 1910-90-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Syntheses of 2-mono- and 2,3-disubstituted quinoxalines was written by Gowenlock, A. H.;Newbold, G. T.;Spring, F. S.. And the article was included in Journal of the Chemical Society in 1945.Name: Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

For the preparation of 2,3-pyrazinedicarboxylic acids carrying certain substituents at the 5- and 5,6-positions, 2-mono- and 2,3-disubstituted quinoxalines have been synthesized. Most of these syntheses depend upon transformations of the readily available Et 2-hydroxy-3-quinoxalinecarboxylate (I). o-C₆H₄(NH₂)₂ (10.8 g.) and 17.4 g. Et ketomalonate in absolute EtOH, refluxed 1 hr., give about 18 g. of I, m. 175.5°-6.5°. Hydrolysis with 3 N NaOH on the steam bath for 30 min. gives 95% of 2-hydroxy-3-quinoxalinecarboxylic acid (II), m. 263-5° (decomposition); at 265°, II yields 72% of 2-hydroxyquinoxaline (III), sublimes at 200°/0.5 mm., m. 271°. III was also prepared in 57% yield from 2.7 g. o-C₆H₄(NH₂)₂ and 3.8 g. EtO₂CCHO in EtOH (refluxing 30 min.). I (10.9 g.) and 50 cc. POCl₃, heated at 110-20° for 10 min., give 90% of Et 2-chloro-3-quinoxalinecarboxylate (IV), m. 42.5° (after sublimation at 60°/6 × 10^-3 mm.); it gradually turns pink in the air and is best stored as the EtOH solution at 0°. Hydrolysis of IV by refluxing with 3 N NaOH for 30 min. gives II; 2 g. of IV and 0.5 g. Na₂CO₃ in 50 cc. 80% MeOH, refluxed 4 hrs., give 1.8 g. of 2-chloro-3-quinoxalinecarboxylic acid (V), pale yellow, m. 146-7° (decomposition); V results also on hydrolysis of IV with aqueous MeOH-NaCN. V in anhydrous EtOH, treated at 0° with dry NH₃ for 4 hrs., gives 85% of the amide, m. 214-15°; it results in small yields from IV and concentrated NH₄OH in 80% MeOH at room temperature IV (4 g.) and 120 cc. EtOH-NH₃ (saturated at 0°), heated 5 hrs. at 150-60°, give 77% of 2-amino-3-quinoxalinecarboxamide, bright yellow, m. 263-4°; refluxed with 10% NaOH for 3 hrs., it yields 2-amino-3-quinoxalinecarboxylic acid (VI), m. 212-13° (decomposition); with MeOH and dry HCl, this yields the HCl salt, light yellow, m. 188-9° (decomposition), of the Me ester, yellow, m. 218-19°. V and glass wool, heated at 0.1 mm. to 160°, give 2-chloroquinoxaline (VII), pale yellow, b_0.5 80°, m. 46-7°; this also results in 85% yield from III and POCl₃ (refluxed 20 min.) and in 18% yield by refluxing II with POCl₃ for 30 min.; a HCl salt seps. from the solution in 10 N HCl. VII and EtOH-NH₃, heated at 150° for 7 hrs., give. 86% of 2-aminoquinoxaline, m. 155-7°, sublimes 130-40°/10^-3 mm.; it also results in 38% yield on heating VI at 250° for 3 min. IV and EtONa in EtOH, refluxed 2 hrs., give 80% of the Et ester, m. 25°, of 2-ethoxy-3-quinoxaline-carboxylic acid (VIII), m. 120-1° (70% yield on hydrolysis of the ester). VIII, heated at 180°, yields 94% of 2-ethoxyquinoxaline, m. 56-8°; it also results in 81% yield from VII and EtONa in EtOH (refluxed 1 hr.). 2,3-Dichloroquinoxaline (IX) and EtONa in EtOH, refluxed 3.5 hrs., give 80% of 2,3-diethoxyquinoxaline, m. 78°; it is not affected by boiling with 0.2 N aqueous EtOH-KOH for 1 hr. but 0.2 g. and 5 cc. HCl (d. 1.19) in 50 cc. EtOH (refluxed 1 hr.) give 2,3-dihydroxyquinoxaline; the 0.1 N NaOH solution exhibits absorption maximum at 3160, 3260, and 3410 A. (ε 12,200, 14,400, and 10,500). IX and EtOH-NH₃, heated 6 hrs. at 150°, give 47% of 2,3-diaminoquinoxaline, m. 328-30° (decomposition). In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Name: Ethyl 3-chloroquinoxaline-2-carboxylate).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxalines have received a significant amount of attention due to their potential use in fighting various pathophysiological conditions like epilepsy, Parkinson’s, and Alzheimer’s diseases. Quinoxalines are used as dyes, pharmaceuticals, and antibiotics such as echinomycin, levomycin exhibiting antitumoral properties. Quinoxalines establish also the basis of anthelmintics and receptor antagonists.Name: Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

An efficient synthesis and biological activity of quinoxaline-2-carboxylic acid and its derivatives was written by Kumar, Navneet;Sharma, Pratima;Kaur, Navjeet;Pareek, Aastha. And the article was included in Journal of Applicable Chemistry (Lumami, India) in 2013.Reference of 49679-45-0 This article mentions the following:

Condensation of ortho phenyldiamine with acetic acid and form 2-tetrahydroxy Bu quinoxaline which further react with hydrogen peroxide and solid sodium hydroxide form quinoxaline-2-carboxylic acid. Ethyl-3-hydroxyquinoxaline-2-carboxylate reacts with POCl₃ and to form ethyl-3-chloroquinoxaline-2-carboxylate. Ethyl-3-chloroquinoxaline-2-carboxylate reacts with sodium hydroxide, alc., sodium methoxide and form 3-ethoxyquinoxaline-2-carboxylic acid, 3-amino quinoxaline-2-carboxylic acid, 3-methoxy quinoxaline-2-carboxylic acid, with good yield. The structure of the compounds was established on the basis of IR, and ¹H NMR, spectral data. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Reference of 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Quinoxaline-1,4-di-N-oxide derivatives have shown to improve the biological results and are endowed with anti-viral, anti-cancer, anti-bacterial, and anti-protozoal activities with application in many other therapeutic areas.Reference of 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis and some reactions of quinoxalinecarboazides was written by Moustafa, O. S.. And the article was included in Journal of the Chinese Chemical Society (Taipei) in 2000.Computed Properties of C11H9ClN2O2 This article mentions the following:

Chlorination of Et (quinoxalin-2(1H)one)-3-carboxylate (I) gave Et (2-chloroquinoxaline)-3-carboxylate (II). Thionation of I by P₂S₅ or II by thiourea yielded the same thione product. Reaction of chloro compound II or the thio compound with hydrazine hydrate gave pyrazolylquinoxaline. The reaction of ester I with thiourea or hydrazine hydrate afforded a pyrimidoquinoxaline or carbohydrazide. The reaction of the carbohydrazide with carbon disulfide in basic medium followed by alkylation afforded oxadiazoloquinoxaline derivatives Carboazide III was produced by reaction of the pyrimidoquinoxaline with nitrous acid. Compound III on heating in an inert solvent, with or without amines, in alcs. or hydrolysis in H₂O undergoes Curtius rearrangements. Reaction of IV with thiosemicarbazide gave a triazoloquinoxaline which on reaction with alkylhalides or hydrazine hydrate yielded S-alkyl or hydrazino derivatives while hydrolysis of IV gave an 3-aminoquinoxalinone which was used as an intermediate. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Computed Properties of C11H9ClN2O2).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.Computed Properties of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider