Heterocyclic Building Blocks-quinoxaline

Application of Diazaphospholidine/Diazaphospholene-Based Bisphosphines in Room-Temperature Nickel-Catalyzed C(sp²)-N Cross-Couplings of Primary Alkylamines with (Hetero)aryl Chlorides and Bromides was written by Gatien, Alexandre V.;Lavoie, Christopher M.;Bennett, Raymond N.;Ferguson, Michael J.;McDonald, Robert;Johnson, Erin R.;Speed, Alexander W. H.;Stradiotto, Mark. And the article was included in ACS Catalysis in 2018.Electric Literature of C8H5ClN2 This article mentions the following:

We report herein on the synthesis and catalytic application of a family of o-phenylene-bridged bisphosphine ancillary ligands featuring a bulky N-heterocyclic phosphine (NHP) donor fragment paired with an adjacent PR₂ donor group (R = alkyl, aryl), whereby the incorporation of phosphorus into either a saturated or unsaturated heterocyclic ring serves as a means of modulating the donicity of the NHP fragment. Screening of these ancillary ligands in representative nickel-catalyzed C(sp²)-N cross-coupling test reactions allowed for the identification of one variant, featuring a saturated NHP structure and an adjacent diphenylphosphino donor group (i.e., NHP-DalPhos), as being particularly effective in reactions involving primary alkylamines. Notably, application of the derived precatalyst (NHP-DalPhos)NiCl(o-tolyl) (C1) enabled the typically challenging monoarylation of structurally diverse primary alkylamines with (hetero)aryl chlorides or bromides at room temperature Also described are the results of our comparative d. functional theory computational anal. of nickel-catalyzed primary alkylamine C(sp²)-N cross-couplings employing PAd-DalPhos or NHP-DalPhos. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Electric Literature of C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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.Electric Literature of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Silver-Catalyzed Three-Component Approach to Quinolines Starting from Anilines, Aldehydes, and Alcohols was written by Zhang, Xu;Liu, Wenmin;Sun, Ruixue;Xu, Xuefeng;Wang, Zhiqiang;Yan, Yanlei. And the article was included in Synlett in 2016.SDS of cas: 49679-45-0 This article mentions the following:

In the presence of AgOTf and triflic acid, anilines, aryl aldehydes and cyclohexanecarboxaldehyde, and alcs. (arylethanols, alkanols, cycloalkanols, and ethylene glycol) underwent regioselective aerobic cyclocondensation reactions in toluene at 120° to yield substituted quinolines. Kinetic isotope effects and competition reactions using preformed imines and reactions of potential intermediates in the cyclocondensation were used to suggest a mechanism for the reaction. The structure of a cyclobutaquinoline was determined by X-ray crystallog. 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. 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: 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

4-Pyrones. 42. Preparation and reactions of 3-acetoacetyl-2-ethoxyquinoxaline was written by Eiden, F.;Bachmann, G.. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 1973.Formula: C11H9ClN2O2 This article mentions the following:

The quinoxaline I (R = COCH2COMe) (II) was prepared in 83% yield by reaction of I (R = CO2Et) with Me2CO-NaH. Reaction of II with N2H4 yielded 92% I (R = 5-methyl-3-pyrazolyl). Reaction of II with o-(H2N)2C6H4 gave 61% I (R = 2-methyl-1,5-benzodiazepin-4-yl). Reaction of II with PhNHNH2 gave 70% I (R = 1- and 2-phenyl-5-methyl-3-pyrazolyl), reaction of II with HONH2 yielded 75% I (R = 5-methyl-3- and 3-methyl-5-isoxazolyl). The single components of these isomeric mixtures were determined by NMR spectra. 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 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.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Reaction of 6-chloroquinoxaline with potassium amide in liquid ammonia was written by Czuba, Wladyslaw;Poradowska, Henryka. And the article was included in Zeszyty Naukowe Uniwersytetu Jagiellonskiego, Prace Chemiczne in 1979.Quality Control of 6-Chloroquinoxaline This article mentions the following:

Amination of 3.292 g 6-chloroquinoxaline with 4-fold excess KNH₂-NH₃ gave traces of 6-aminoquinoxaline together with 2.141 g 3-amino-6-chloroquinoxazaline and 0.413 g 2,3-diamino-6-chloroquinoxaline. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Quality Control of 6-Chloroquinoxaline).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Quality Control of 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis, characterization and biological evaluation of some quinoxaline derivatives: a promising and potent new class of antitumor and antimicrobial agents was written by Al-Marhabi, Aisha R.;Abbas, Hebat-Allah S.;Ammar, Yousry A.. And the article was included in Molecules in 2015.Formula: C8H5BrN2O2 This article mentions the following:

The synthesis of quinoxaline derivatives, e.g., tetrazolo[1,5-a]quinoxalines I (R = Cl, piperidin-1-yl, morpholin-4-yl), N-pyrazoloquinoxalines, 1,2,4-triazinoquinoxalines and 1,2,4-triazoloquinoxalines, was described. All the synthesized compounds were evaluated for their antitumor, antifungal and antibacterial activities. The results indicated that tetrazolo[1,5-a]quinoxalines I showed the highest inhibitory effects towards the tested tumor cell lines, as compared to the reference doxorubicin. Also, most of the synthesized compounds exhibited a good degree of inhibition against tested strains of Gram pos. and neg. bacteria, as well as fungi. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Formula: C8H5BrN2O2).

6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) 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. 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: C8H5BrN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quinoxaline chemistry. Part 13: 3-carboxy-2-benzylamino-substituted quinoxalines and N-[4-[(3-carboxyquinoxalin-2-yl)aminomethyl]benzoyl]-L-glutamates: synthesis and evaluation of in vitro anticancer activity was written by Corona, Paola;Vitale, Gabriella;Loriga, Mario;Paglietti, Giuseppe. And the article was included in Farmaco in 2000.Application In Synthesis of Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

Among a new series of 28 3-carboxy or carbethoxy quinoxalines bearing a substituted benzylamino or N-[4-(aminomethyl)benzoyl]glutamate group on position 2 of the ring and various substituents at C-6, 7 positions, 21 were selected at the National Cancer Institute for evaluation of their in vitro anticancer activity. The results obtained seem to confirm that the carboxy or carbethoxy group on position 3 is not helpful, with a few exceptions, for the anticancer activity. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Application In Synthesis of 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. 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.Application In Synthesis of Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Effect of a novel 5-HT3 receptor antagonist 3-methoxy-N-P-tolylquinoxalin-2-carboxamide (QCM-4) on the acute and chronic rodent models of depression was written by Kurhe, Yeshwant Vijay;Radhakrishnan, Mahesh;Gupta, Deepali;Thangaraj, Devodoss. And the article was included in International Journal of Pharmacy and Pharmaceutical Sciences in 2013.Synthetic Route of C11H9ClN2O2 This article mentions the following:

Objective: 5-HT3 receptor the only type of ion channel among the family of serotonergic receptors which is recognized as a potential novel therapeutic target for depression, anxiety and cognition. In the present work was designed to evaluate the antidepressant-like effect of a novel 5-HT3 antagonist 3-methoxy-N-p-tolylquinoxalin-2-carboxamide (QCM-4) in a battery of behavioral acute and chronic rodent models of depression. Methods: Behavioral models with high predictive validities like forced swim test (FST) and tail suspension test (TST) in mice along with mechanistic models including 5-hydroxytryptamine (5-HTP) induced head twich response in mice and reserpine induced hypothermia in rats were used for screening QCM-4. Chronic surgical model of olfactory balbectomy (OBX) was performed and further evaluated by sucrose preference test and open field test (OFT) for anti-depressant like effect of QCM-4. Results: Following were the principle findings in the present research; Firstly, QCM-4 dose dependently reduced the immobility duration in FST and TST. Secondly, in the mechanistic models, QCM-4 dose dependently potentiated 5-HTP induced head twich response and attenuated the reserpine induced hypothermia. Lastely, in the surgical OBX model, QCM-4 reversed the anhedonia and behavioral alterations in animals which was evaluated by increase in the sucrose consumption and reduction in ambulation, fecal contents as well as number of rearings in OFT by QCM-4 treated OBX animals compared to OBX control. Conclusion: The results of the present study, indicates that QCM-4, a novel 5-HT3 receptor antagonist exhibit an anti-depressant like effect. Our further studied will be focused on the chronic unpredictable mild stress induced alterations and mol. mechanism involved in the anti-depressant like action of QCM-4. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Synthetic Route 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. 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.Synthetic Route of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ligand-Based Design, Synthesis, and Pharmacological Evaluation of 3-Methoxyquinoxalin-2-carboxamides as Structurally Novel Serotonin Type-3 Receptor Antagonists was written by Mahesh, Radhakrishnan;Devadoss, Thangaraj;Dhar, Arghya Kusum;Venkatesh, Sudali Muthu;Mundra, Sourabh;Pandey, Dilip Kumar;Bhatt, Shvetank;Jindal, Ankur Kumar. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2012.Formula: C11H9ClN2O2 This article mentions the following:

Employing a ligand-based approach, 3-methoxyquinoxalin-2-carboxamides were designed as serotonin type-3 (5-HT₃) receptor antagonists and synthesized from the starting material o-phenylenediamine in a sequence of reactions. The structures of the synthesized compounds were confirmed by spectral data. These carboxamides were investigated for their 5-HT₃ receptor antagonisms in longitudinal muscle myenteric plexus preparations from guinea-pig ileum against a standard 5-HT₃ agonist, 2-methyl-5-HT, and their antagonism activities are expressed as pA₂ values. Some compounds exhibited antagonism greater than that of the standard 5-HT₃ antagonist, ondansetron. 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 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. 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.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis and evaluation of in vitro antiproliferative activity of new ethyl 3-(arylethynyl)quinoxaline-2-carboxylate and pyrido[4,3-b]quinoxalin-1(2H)-one derivatives was written by Hajri, Majdi;Esteve, Marie-Anne;Khoumeri, Omar;Abderrahim, Raoudha;Terme, Thierry;Montana, Marc;Vanelle, Patrice. And the article was included in European Journal of Medicinal Chemistry in 2016.Name: Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

A novel series is presented of quinoxaline derivatives, i.e. I, from which agents with antiproliferative activity have been identified. Two Et 3-(arylethynyl)quinoxaline-2-carboxylates demonstrated substantial antiproliferative activity against both human non-small cell lung carcinoma (A549) and glioblastoma (U87-MG) cell lines. Pyrido[4,3-b]quinoxalin-1(2H)-ones demonstrated poor activity against A549 and U87-MG cell lines. Three of the derivatives in Et 3-(arylethynyl)quinoxaline-2-carboxylate series demonstrated substantial antiproliferative activity. Two arylethynyl derivatives proved to be the most cytotoxic with an IC₅₀ value of 3.3 μM for both A549 and U87-MG cell lines. 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. 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.Name: Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A green synthesis of quinoxalines and 2,3-dihydropyrazines was written by Delpivo, Camilla;Micheletti, Gabriele;Boga, Carla. And the article was included in Synthesis in 2013.Formula: C8H5ClN2 This article mentions the following:

Quinoxaline and dihydropyrazine derivatives were obtained in high yields by simple cyclocondensation of 1,2-diamines with 1,2-dicarbonyl compounds in water. In some cases, the products spontaneously precipitated from the reaction mixture, making it possible to recover and reuse the mother liquor for further condensations. The very mild reaction conditions, the high yields of the products, and the absence of any catalyst make this methodol. an efficient and green route to quinoxalines and dihydropyrazines. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Formula: C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. 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.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider