Day: February 9, 2023

Prodrug Approach toward the Development of a PET Radioligand for Imaging the GluN2A Subunits of the NMDA Receptor was written by Gruber, Stefan;Waser, Valerie;Thiel, Zacharias;Ametamey, Simon M.. And the article was included in Organic Letters in 2021.Reference of 532934-95-5 This article mentions the following:

A straightforward synthesis of a F-18-labeled prodrug of AFA233 is reported. The key step in the preparation of [¹⁸F]AFA233-prodrug is the selective deprotection of the tert-Bu protection groups of the quinoxalinedione moiety without cleavage of the tert-butyl-S-acyl-2-thioethyl protection groups on the phosphate esters. The preparation of the nonradioactive prodrug reference compound of AFA233 is reported. In the experiment, the researchers used many compounds, for example, 7-Bromo-5-methylquinoxaline (cas: 532934-95-5Reference of 532934-95-5).

7-Bromo-5-methylquinoxaline (cas: 532934-95-5) 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.Reference of 532934-95-5

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ³-Iodinane Compounds was written by Troian-Gautier, Ludovic;De Winter, Julien;Gerbaux, Pascal;Moucheron, Cecile. And the article was included in Journal of Organic Chemistry in 2013.Application of 5448-43-1 This article mentions the following:

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chem. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Application of 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. 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.Application of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed N-Arylation of Fluoroalkylamines was written by McGuire, Ryan T.;Yadav, Arun A.;Stradiotto, Mark. And the article was included in Angewandte Chemie, International Edition in 2021.Synthetic Route of C8H5ClN2 This article mentions the following:

The Ni-catalyzed N-arylation of β-fluoroalkylamines with broad scope is reported for the first time. Use of the air-stable pre-catalyst (PAd2-DalPhos)Ni(o-tol)Cl allows for reactions to be conducted at room temperature (25°C, NaOtBu), or by use of a com. available dual-base system (100°C, DBU/NaOTf), to circumvent decomposition of the N-(β-fluoroalkyl)aniline product. The mild protocols disclosed herein feature broad (hetero)aryl (pseudo)halide scope (Cl, Br, I, and for the first time phenol-derived electrophiles), encompassing base-sensitive substrates and enantioretentive transformations, in a manner that is unmatched by any previously reported catalyst system. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Synthetic Route of C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. 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.Synthetic Route of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis, Photophysical Properties, and Antimicrobial Activity of Novel Styryl Colorants Derived from 7-Methoxy-1,4-diphenethyl-1,2,3,4-tetrahydroquinoxaline-6-carbaldehyde was written by Jarag, K. J.;Jagtap, A. R.;Borse, B. N.;Shukla, S. R.;Shankarling, G. S.. And the article was included in Journal of Heterocyclic Chemistry in 2012.Safety of 6-Methoxyquinoxaline This article mentions the following:

The novel 1,4-diphenethyl-1,2,3,4-tetrahydro-7-methoxyquinoxalin-6-carbaldehyde was synthesized by reductive alkylation of 6-methoxy quinoxaline with Ph acetic acid and was further subjected to Knoevenagel condensation with various active methylene compounds to synthesize novel styryl colorants. Photophys. properties of styryl colorants were studied using UV-visible and fluorescence spectroscopy. These colorants displayed orange to violet hue and showed fluorescence emission maxima in the region of 560-640 nm, and displayed a large Stokes shift (85-104 nm). Compounds were subjected to thermogravimetric anal. which showed excellent stability up to 310°C. These styryl compounds were evaluated for their antimicrobial study as antifungal against Candida albicans C. albicans and Aspergillus niger and antibacterial against Escherichia coli and Staphylococcus aureus. The results revealed good antimicrobial activity against tested organisms. The synthesized chromophores were characterized using elemental anal., FTIR, ¹³C-NMR and ¹H-NMR spectroscopy and mass spectrometry. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Safety of 6-Methoxyquinoxaline).

6-Methoxyquinoxaline (cas: 6639-82-3) 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.Safety of 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

1-Alkyl-1,2,3,4-tetrahydroquinoxalines was written by Cavagnol, J. C.;Wiselogle, F. Y.. And the article was included in Journal of the American Chemical Society in 1947.Formula: C9H8N2O This article mentions the following:

3,4-(H₂N)₂C₆H₃Me results in 86.5% yield on reduction of 3,4-O₂N(H₂N)C₆H₃Me over Raney Ni and 3,4-(H₂N)₂C₆H₃OMe in 86% yield, from 3,4-O₂N(H₂N)C₆H₃OMe. o-C₆H₄(NH₂)₂ (108.1 g.) in 500 cc. 2 M AcOH and 250 cc. 4 M AcONa at 60°, poured rapidly into 298.4 g. (CHO)₂.2NaHSO₃.H₂O in 1500 cc. H₂O at 60°, the solution stirred 1 hr., cooled to below 10°, neutralized with 120 g. NaOH, 500 g. K₂CO₃ added, the oily amine extracted with one 500-cc. portion of C₆H₆, and the solution extracted 8 hrs. with 300 cc. C₆H₆, gives 85% quinoxaline (I), b₁ 44-5°, b₁₀ 96°, b₃₁ 124°, b₇₆₀ 225°, m. 30.5-1.5°; 6-Cl derivative b₁₀ 117-19°, m. 63.8-4.3°, 79%; 6-Me derivative b₁ 86°, b₂₉ 141.5°, m. below 0°, 86%; 6-MeO derivative b₇ 128°, m. 60°, 88%. I (130.1 g.) in 1200 cc. C₆H₆, shaken with 10 cc. moist Raney Ni to remove catalyst poisons, and then reduced over 1.5 g. Pt oxide at 50-80 lb. pressure, give 92% 1,2,3,4-tetrahydroquinoxaline (II), m. 98.5-9° (HCl salt, m. 167-9°); 6-Cl derivative m. 113-14°; 6-Me derivative m. 104.5-5.5°, 92%; 6-MeO derivative m. 80.5-1°, 95%. A variety of methods for the monoalkylation of II failed. II (40.3 g.) in 350 cc. 20% NaOH at 20°, treated dropwise with 115 cc. PhSO₂Cl (60 drops/min.) during 2.5-3 hrs. (vigorous stirring), gives 87% 1,2,3,4-tetrahydro-1-phenylsulfonylquinoxaline (III), yellow, m. 138-9°; with C₅H₅N, 10% excess PhSO₂Cl is sufficient and the III has a red tinge. III (0.1 mole), 0.4 mole alkyl halide, 0.2 mole anhydrous Na₂CO₃, and 100 cc. 95% EtOH, refluxed 48 hrs. in a N atm., give 88-92% of 1-substituted derivatives: Me, m. 88-9° (methiodide, m. 168-9°); Et, m. 118.5-19.5°; Pr, m. 119.5-20°; iso-Pr, m. 142.5-3.5°; Bu, m. 95-5.5°; benzyl, m. 134-5°; Ac, m. 111.5-12°. Hydrolysis with concentrated H₂SO₄ gives 1-alkyl-1,2,3,4-tetrahydroquinoxalines: Me, b₂ 108.5°, 76%; Et, b₁ 88-90°, 59% (oxalate, m. 130-1°); Pr, b_1.5 113.5°, 66%; iso-Pr, b_1.5 107.5°, 68%; Bu, b₁ 107.5°, 81% (oxalate, m. 142.5-3.5°); benzyl, b_1.5 178-9°, m. 50.5-2.5°, 66%. Picrates: II, m. 128.5-9.5°; 1-Me, m. 123-6.5°; 1-Et, m. 111.5-12°; 1-Pr, m. 135-6°; 1-iso-Pr, m. 131-2°; 1-Bu, m. 130-1.5°; 1-benzyl, m. 150-1.5°; 6-MeO, m. 134-5°; 6-Me, m. 148-8.5°. Derivatives of 1-benzoyl-1,2,3,4-tetrahydroquinoxaline: 4-Me, m. 109-10°; 4-Et, m. 123-4°; 4-Pr, m. 88-9°; 4-iso-Pr, m. 114-15°; 4-Bu, m. 87-8°; 4-benzyl, m. 123.3-3.8°. 1,4-Dibenzoyl-1,2,3,4-tetrahydroquinoxalines: 6-Me, m. 141.5-2°; 6-MeO, m. 138.5-8.8°; 6-Cl, m. 168.5-9°. 1,4-Diacetyl-6-methyl-1,2,3,4-tetrahydroquinoxaline m. 105.2-6.2°. 1,4-Dicarbethoxy-1,2,3,4-tetrahydroquinoxaline, m. 42-4°; the trihydrate is an oil. 1,4-Bis (phenylsulfonyl)-6-methyl-1,2,3,4-tetrahydroquinoxaline m. 124-5°. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Formula: C9H8N2O).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Formula: C9H8N2O

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider