145.16| Heterocyclic Building Blocks-quinoxaline

Holzhauer, Laura et al. published their research in Beilstein Journal of Organic Chemistry in 2022 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) belongs to quinoxaline derivatives. Compounds possessing quinoxaline derivatives were bestowed with a variety of significant biological properties such as antiviral, antimalarial, anticancer, DNA intercalation, DNA duplex stabilization, and many others. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Quality Control of Quinoxalin-2-amine

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof was written by Holzhauer, Laura;Liagre, Chloe;Fuhr, Olaf;Jung, Nicole;Braese, Stefan. And the article was included in Beilstein Journal of Organic Chemistry in 2022.Quality Control of Quinoxalin-2-amine This article mentions the following:

The conversion of tetrazolo[1,5-a]quinoxalines I (R = H, i-Pr, Ph, etc.) to 1,2,3-triazoloquinoxalines II (R¹ = n-Bu, Ph, 1,3-dioxo-isoindolinylmethyl, etc.) and triazoloimidazoquinoxalines III (R¹ = Ph, n-Bu)under typical conditions of a CuAAC reaction has been investigated. Derivatives of the novel compound class of triazoloimidazoquinoxalines (TIQ) and rhenium(I) triazoloquinoxaline complexes IV and [N,N-diethyl-2-(1-(quinoxalin-2-yl)-1H-1,2,3-triazol-4-yl)ethan-1-amine]bromotricarbonylrhenium(I) as well as a new TIQ rhenium complex such as [1-butyl-4-(4-butyl-1H-1,2,3-triazol-1-yl)imidazo[1,2-a]quinoxaline]bromotricarbonylrhenium(I) were synthesized. As a result, a small 1,2,3-triazoloquinoxaline library was obtained and the method could be expanded towards 4-substituted tetrazoloquinoxalines. The compatibility of various aliphatic and aromatic alkynes R¹CCH towards the reaction was investigated and the denitrogenative annulation towards imidazoloquinoxalines V could be observed as a competing reaction depending on the alkyne concentration and the substitutions at the quinoxaline. In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Quality Control of Quinoxalin-2-amine).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Weijlard, John et al. published their research in Journal of the American Chemical Society in 1944 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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.Product Details of 5424-05-5

Sulfaquinoxaline and some related compounds was written by Weijlard, John;Tishler, Max;Erickson, A. E.. And the article was included in Journal of the American Chemical Society in 1944.Product Details of 5424-05-5 This article mentions the following:

Alloxazine (I) (10 g.) and 50 cc. concentrated NH₄OH, heated in a steel bomb at 170-5° for 5 h., give 71.3% of 2-amino-3-quinoxalinecarboxylic acid (II), m. 204°. II (2 g.) in 8 cc. PhNO₂, refluxed 10 min., give 92% of 2-aminoquinoxaline (III), m. 155-6°; I (2 g.) and 10 cc. 95% H₂SO₄, heated at 240-5° for 10 min., give 56% of III. Ac derivative of III, yellow, m. 192.5-3.5°. II (10 g.) and alc. HCl, refluxed 3 h., give 8.5 g. of the Et ester (IV), m. 165-6° (HCl salt, m. 173-5°). From 0.69 g. III in 200 cc. reagent C₅H₅N at -5° treated (after 2 min.) with 1.23 g. AcNHC₆H₄SO₂Cl (V), with alternate additions of III and V at 5-min. intervals until 20.7 g. of III and 36.9 g. of V had been added at 0°, stirred 1 h. at 0° and 4 h. at room temperature, concentrated to dryness and washed with H₂O at 0°, there resulted 91.2% of 2-N⁴-acetylsulfanilamidoquinoxaline, m. 243-4°; refluxing 6 g. with 25 cc. concentrated HCl and 50 cc. EtOH for 1 h. gives 3.85 g. of 2-sulfanilamidoquinoxaline (VI), m. 247-8°; N⁴-Bz derivative, m. 259-60°; N⁴-caproyl derivative, m. 199-200°; β-carboxypropionyl derivative, m. 234-5°. 2-N⁴-Acetylsulfanilamido-3-carbethoxyquinoxaline, m. 236-7°. Condensation of IV and V, followed by hydrolysis, gives 2-sulfanilamido-3-carboxyquinoxaline, m. 238-9°. II could not be condensed with V. Preliminary chemotherapeutic studies indicate that VII is very effective in bacterial infections and that it has the unusual property of being eliminated by animals very slowly so that effective concentrations can be maintained by administering it at comparatively infrequent intervals. In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Product Details of 5424-05-5).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nassar, Rania et al. published their research in Environmental Science and Pollution Research in 2018 | CAS: 5424-05-5

Transformation of sulfaquinoxaline by chlorine and UV light in water: kinetics and by-product identification was written by Nassar, Rania;Mokh, Samia;Rifai, Ahmad;Chamas, Fatmeh;Hoteit, Maha;Al Iskandarani, Mohamad. And the article was included in Environmental Science and Pollution Research in 2018.Reference of 5424-05-5 This article mentions the following:

Sulfaquinoxaline (SQX) is an antimicrobial of the sulfonamide class, frequently detected at low levels in drinking and surface water as organic micropollutant. The main goal of the present study is the evaluation of SQX reactivity during chlorination and UV irradiations which are two processes mainly used in water treatment plants. The SQX transformation by chlorination and UV lights (254 nm) was investigated in purified water at common conditions used for water disinfection (pH = 7.2, temperature = 25°C, [chlorine] = 3 mg L^-1). The result shows a slow degradation of SQX during photolysis compared with chlorination process. Kinetic studies that fitted a fluence-based first-order kinetic model were used to determine the kinetic constants of SQX degradation; they were equal to 0.7 × 10^-4 and 0.7 × 10^-2 s^-1corresponding to the half time lives of 162 and 1.64 min during photolysis and chlorination, resp. In the second step, seven byproducts were generated during a chlorination and photo-transformation of SQX and identified using liquid chromatog. with electrospray ionization and tandem mass spectrometry (MS-MS). SO₂ extrusion and direct decomposition were the common degradation pathway during photolysis and chlorination. Hydroxylation and isomerization were observed during photodegradation only while electrophilic substitution was observed during chlorination process. In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Reference of 5424-05-5).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Willems, Sabine et al. published their research in ChemMedChem in 2022 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. 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.Safety of Quinoxalin-2-amine

Scaffold Hopping from Amodiaquine to Novel Nurr1 Agonist Chemotypes via Microscale Analogue Libraries was written by Willems, Sabine;Mueller, Marcel;Ohrndorf, Julia;Heering, Jan;Proschak, Ewgenij;Merk, Daniel. And the article was included in ChemMedChem in 2022.Safety of Quinoxalin-2-amine This article mentions the following:

Several lines of evidence suggest the ligand-sensing transcription factor Nurr1 as a promising target to treat neurodegenerative diseases. Nurr1 modulators to validate and exploit this therapeutic potential are rare, however. To identify novel Nurr1 agonist chemotypes, we have employed the Nurr1 activator amodiaquine as template for microscale analog library synthesis. The first set of analogs was based on the 7-chloroquiolin-4-amine core fragment of amodiaquine and revealed superior N-substituents compared to diethylaminomethylphenol contained in the template. A second library of analogs was subsequently prepared to replace the chloroquinolineamine scaffold. The two sets of analogs enabled a full scaffold hop from amodiaquine to a novel Nurr1 agonist sharing no structural features with the lead but comprising superior potency on Nurr1. Addnl., pharmacophore modeling based on the entire set of active and inactive analogs suggested key features for Nurr1 agonists. In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Safety of Quinoxalin-2-amine).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Iijima, Chihoko et al. published their research in Yakugaku Zasshi in 1989 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) belongs to quinoxaline derivatives. Compounds possessing quinoxaline derivatives were bestowed with a variety of significant biological properties such as antiviral, antimalarial, anticancer, DNA intercalation, DNA duplex stabilization, and many others. 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.Quality Control of Quinoxalin-2-amine

Quinoxalines. XXV. Synthesis and chemical properties of 2-nitroquinoxaline was written by Iijima, Chihoko. And the article was included in Yakugaku Zasshi in 1989.Quality Control of Quinoxalin-2-amine This article mentions the following:

2-Nitroquinoxaline (I) was synthesized and the chem. properties were investigated. The reaction of 2-iodoquinoxaline with AgNO₂ in the presence of Bu₄NF gave 44% I. I is quite reactive toward various nucleophiles and the ipso-substitution reaction of I with O-nucleophiles (OH^–, CH₃O^–, C₂H₅O^–, C₈H₅O^–), S-nucleophiles (CH₃S^–, C₆H₅S^–, p-CH₃C₆H₅SO₂^–), N-nucleophiles (hexylamine, cyclohexylamine, piperidine, morpholine, aniline), and C-nucleophiles (CN^–, di-Et malonate, malonodinitrile, benzyl cyanide, Et cyanoacetate, nitroethane, acetophenone) readily afforded the corresponding 2-substituted quinoxalines. In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Quality Control of Quinoxalin-2-amine).

Quinoxalin-2-amine (cas: 5424-05-5) belongs to quinoxaline derivatives. Compounds possessing quinoxaline derivatives were bestowed with a variety of significant biological properties such as antiviral, antimalarial, anticancer, DNA intercalation, DNA duplex stabilization, and many others. 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.Quality Control of Quinoxalin-2-amine

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Iijima, Chihoko et al. published their research in Yakugaku Zasshi in 1988 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) 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 in the treatment of bacterial, cancer, and HIV infections. Moreover, varenicline, a clinical drug is used for treating nicotine addiction, also contains quinoxaline moiety.Category: quinoxaline

Quinoxalines. XXIII. Reaction of 2-chloroquinoxaline with nucleophiles was written by Iijima, Chihoko;Hayashi, Eisaku. And the article was included in Yakugaku Zasshi in 1988.Category: quinoxaline This article mentions the following:

2-Chloroquinoxaline (I, R = Cl) reacted with NaI, NaSO₂C₆H₄R¹-4 (R¹ = H, Me), or KSCN to afford quinoxaline derivatives I (R = I, SO₂C₆H₄R¹-4, SCN; R¹ = H, Me) in good yields. Cyano and nitro groups were introduced into the 2-position of quinoxaline in low yield by using KCN and AgNO. In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Category: quinoxaline).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ji, Yuefei et al. published their research in Environmental Science and Pollution Research in 2017 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. 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.Computed Properties of C8H7N3

Ferrous-activated peroxymonosulfate oxidation of antimicrobial agent sulfaquinoxaline and structurally related compounds in aqueous solution: kinetics, products, and transformation pathways was written by Ji, Yuefei;Wang, Lu;Jiang, Mengdi;Yang, Yan;Yang, Peizeng;Lu, Junhe;Ferronato, Corinne;Chovelon, Jean-Marc. And the article was included in Environmental Science and Pollution Research in 2017.Computed Properties of C8H7N3 This article mentions the following:

Sulfaquinoxaline (SQX) is a coccidiostatic drug widely used in poultry and swine production and has been frequently detected in various environmental compartments such as surface water, groundwater, soils, and sediments. In the present study, degradation of SQX by ferrous ion-activated peroxymonosulfate oxidation process (Fe(II)/PMS), a promising in situ chem. oxidation (ISCO) technique, was systematically investigated. Exptl. results showed that Fe(II)/PMS process appeared to be more efficient for SQX removal relative to Fe(II)/persulfate process (Fe(II)/PS). An optimal Fe(II):PMS molar ratio of 1:1 was found to be necessary for efficient removal of SQX. Increasing the solution pH hampered the degradation of SQX, and no enhancement in SQX degradation was observed when chelating agents S,S鈥?ethylenediamine-N,N鈥?disuccinic acid (EDDS) and citrate were present. The presence of Suwannee River fulvic acid (SRFA), as a representative of aquatic natural organic matter (NOM), could inhibit the degradation of SQX. SQX was more susceptible to Fe(II)/PMS oxidation in comparison to its substructural analog 2-amino-quinoxaline (2-AQ) and other sulfonamides, i.e., sulfapyridine (SPD) and sulfadiazine (SDZ). Transformation products of SQX were enriched by solid-phase extraction (SPE) and identified by liquid chromatog.-electrospray ionization-triple quadrupole mass spectrometry (LC-ESI-MS/MS). On the basis of the TPs identified, detailed reaction pathways for SQX degradation including sulfonamide bond cleavage, SO₂ extrusion, and aniline moiety oxidation were proposed. Our contribution may provide some useful information for better understanding the kinetics and mechanisms of SQX degradation by sulfate radical-based advanced oxidation processes (SR-AOPs). In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5Computed Properties of C8H7N3).

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Elina, A. S. et al. published their research in Zhurnal Obshchei Khimii in 1963 | CAS: 5424-05-5

Quinoxalin-2-amine (cas: 5424-05-5) 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.HPLC of Formula: 5424-05-5

N-Oxides of the quinoxaline series. VI. N-Oxides of amino and hydroxy derivatives of quinoxaline was written by Elina, A. S.;Tsirul’nikova, L. G.. And the article was included in Zhurnal Obshchei Khimii in 1963.HPLC of Formula: 5424-05-5 This article mentions the following:

2-Acetamidoquinoxaline in 10.3% AcO₂H in the presence of NaOAc (22 h. at 45-8掳) gave 50% 1,4-di-N-oxide, decomposed 233掳, and 4.5% more soluble 2-amino-3-hydroxyquinoxaline 1,4-di-N-oxide (Ia), decomposed 300掳. Reaction with AcO₂H (48 h. at 20-5掳) gave 20% 2-acetamidoquinoxaline 1-N-oxide, m. 193-4掳, and 6% corresponding 4-N-oxide, m. 239-40掳, insoluble in CHCl₃; the residue contained a mixture of these oxides. Heating 2-acetamidoquinoxaline in AcOH with 30% H₂O₂ in the presence of Na₄P₂O₇ 22 h. at 55-60掳 gave 20% Ia and mixed mono-N-oxides. 2-Amino-3-methylquinoxaline refluxed with Ac₂O 0.5 h. gave 65% diacetyl derivative (I), m. 87.5-8掳; similar reaction in MePh in 2 h. gave 85% 2-acetamido-3-methylquinoxaline, m. 145-6掳. I and 10% AcO₂H in the presence of H₂SO₄ (22 h. at 50掳) gave on evaporation and treatment with MeOH-Et₂O 25% 4-N-oxide, m. 208-9掳, identified as that of 2-acetamido-3-methylquinoxaline; the residue gave some mono-N-oxide of I, m. 144.5-6掳. 2-Acetamido-3-methylquinoxaline heated 22.5 h. in AcOH with 30% H₂O₂ at 60掳 gave 62.7% 2-amino-3-methylquinoxaline 1,4-di-N-oxide, decomposed 215-16掳. Heating the N-oxides of 2-acetamidoquinoxalines with 2.5N HCl 10-12 min. at 100掳 gave: 2-aminoquinoxaline 1,4-di-N-oxide (II), decomposed 242掳, 89.5%, which gave a green color with FeCl₃; 2-aminoquinoxaline 1-N-oxide (IIa), m. 191-2掳, 75.9%, bluegreen color with FeCl₃; 2-aminoquinoxaline 4-N-oxide (IIb), decomposed 276掳, 70.3%, gave no color with FeCl₃; 2-aminoquinoxaline 4-N-oxide (IIb) decomposed 276掳, 70.3%, gave no color with FeCl₃; 2-amino-3-methylquinoxaline 4-N-oxide, m. 208-9掳, 80.2%, gave no color with FeCl₃. Longer heating with 2.5N HCl resulted in isomerization of N oxides into o-hydroxy compounds and 2-10 h. heating gave the following from the above oxides: II gave in 0.5 h. mainly 2-amino-3-hydroxyquinoxaline 1-N-oxide (III), decomposed 300掳, and 10% 2,3-dihydroxyquinoxaline, did not m. <360掳; the former gave green color with FeCl₃; similar reaction in 10 h. gave 2,3-dihydroxyquinoxaline 1-N-oxide (IV), decomposed 279-80掳, which gave red color with FeCl₃. III in 4 h. gave IV. IIa in 13.5 h. gave 30% IIa.HCl, decomposed 241.5掳, and unchanged IIa. IIb in 2 h. gave mainly 2-amino-3-hydroxyquinoxaline, did not m. <360掳, and 20% 2,3-dihydroxyquinoxaline, did not m. <360掳, 2-amino-3-hydroxy-quinoxaline 1,4-di-N-oxide in 4 h. gave 65% 2,3-dihydroxyquinoxaline 1,4-di-N-oxide, decomposed 261-2.5掳. The R_f values for paper chromatog. of the oxides in BuOH-5% AcOH system are tabulated. II refluxed 0.5 h. in N NaOH gave (on acidification to pH 5) 55% III; IIa in 4 h. gave 65% 2-hydroxyquinoxaline 1-N-oxide (V), m. 207-8掳; mixed 1- and 4-N-oxides of 2-acetamidoquinoxaline in 0.5 h. gave mainly V and IIa, with some IIb; similarly, 2-amino-3-methylquinoxaline 1,4-di-N-oxide gave in 5.5 h. 30% 2-hydroxy-3-methylquinoxaline 1,4- di-N-oxide, decomposed 216-17掳, and unchanged starting material. Shaking the N-oxides in H over Raney Ni at room temperature in aqueous MeOH or aqueous NaOH or EtOH-AcOH gave the following results: II gave 2-aminoquinoxaline, m. 150-1掳; 2-amino-3-hydroxyquinoxaline 1,4-di-N-oxide gave the 4-N-oxide, decomposed 282掳, and 2-amino-3-hydroxyquinoxaline. IV gave 2,3-dihydroxyquinoxaline, while IIa was largely unchanged and gave some unidentified product (undescribed). In the experiment, the researchers used many compounds, for example, Quinoxalin-2-amine (cas: 5424-05-5HPLC of Formula: 5424-05-5).

Quinoxalin-2-amine (cas: 5424-05-5) 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.HPLC of Formula: 5424-05-5

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider