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Journal articles on the topic 'Quinoxaline ring'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

El-Telbani, Emad M., Ibrahim Radini, and Sameh R. Elgogary. "Syntheses of tricyclic fused quinoxaline ring systems: Pyrazoloquinoxalines (a-review)." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 279. https://doi.org/10.59467/ijhc.2025.35.279.

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Quinoxaline derivatives have gained significant interest due to their diverse pharmacological activity and have been included in numerous marketed drugs used to treat of various diseases. Examples include glecaprevir (Mavyret), voxilaprevir (Vosevi), Balversa (L01EX16) (erdafitinib), carbadox, XK469R (NSC698215), and becampanel (AMP397). Among the five-membered fused tricyclic quinoxalines ring systems, the pyrazoloquinolines belong to the azaheterocyclic group as derivatives of quinoxalines and pyrazoles and have characterized by many biological and pharmaceutical properties. There are three

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2

Elgogary, Sameh R., Emad M. El-Telbani, and Ibrahim Radini. "Syntheses and Biological Activities of Tricyclic-fused Quinoxaline Ring Systems (A Review). Part I: Thienoquinoxalines." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 34, no. 02 (2024): 173. http://dx.doi.org/10.59467/ijhc.2024.34.173.

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Quinoxaline derivatives are an interesting class of heterocyclic compounds in drug discovery. It is rare in natural state, but their synthesis is easy to perform coupling between benzene and pyrazine rings. In addition, quinoxaline nucleus has received notable attention as an important pharmacophore that has broad-spectrum applications, especially in the fields of pharmaceutics and medicine. This review spotlights the biological activities and the different methods of preparation of three isomers of thienoquinoxalines, namely thieno[2,3-b]quinoxaline, thieno[3,4-b]quinoxaline, and thieno[2,3-g

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3

Ridhima, Chauhan, S. Chundawat N., and Pal Singh Girdhar. "Quinoxaline Derivatives: Synthesis and Biological Significance." Pharmaceutical and Chemical Journal 10, no. 3 (2023): 137–47. https://doi.org/10.5281/zenodo.13995628.

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Quinoxaline is a well-known and important nitrogen-containing heterocyclic compound with a complex ring consisting of a benzene ring and a pyrazine ring. Different modified quinoxalines and their derivatives with various functional groups are an important part of biological science, and important research projects are introduced in this course. Many methods have been developed to combine them. The demonstration that many quinoxaline derivatives have many biological activities encourages research in this field. There are many useful drugs such as antibiotics, antibiotics, antibiotics, antibioti

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4

Ou, Zhongping, Wenbo E, Jianguo Shao, et al. "Electrochemical and spectroelectrochemical properties of building blocks for molecular arrays: reactions of quinoxalino[2,3-b]porphyrins containing metal(II) ions." Journal of Porphyrins and Phthalocyanines 09, no. 02 (2005): 142–51. http://dx.doi.org/10.1142/s1088424605000216.

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Quinoxalino[2,3-b]porphyrins are laterally-extended porphyrins with aromatic ring systems fused to the β,β'-positions of a pyrrolic ring of the macrocycle. They are building blocks for coplanar laterally-extended oligoporphyrins with applications in molecular electronics. The electrochemistry and spectroelectrochemistry of four such quinoxalinoporphyrins containing metal(II) ions and one free-base quinoxalinoporphyrin dissolved in nonaqueous media have been investigated and the data are compared to that seen for the same derivatives of the parent macrocycle lacking the fused quinoxaline ring.

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5

Zayed, Mohamed F. "Chemistry, Synthesis, and Structure Activity Relationship of Anticancer Quinoxalines." Chemistry 5, no. 4 (2023): 2566–87. http://dx.doi.org/10.3390/chemistry5040166.

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Quinoxaline is a fused heterocycle system of a benzene ring and pyrazine ring. It has earned considerable attention due to its importance in the field of medicinal chemistry. The system is of extensive importance due to its comprehensive array of biological activities. Quinoxaline derivatives have been used as anticancer, anticonvulsant, anti-inflammatory, antidiabetic, antioxidant, antibacterial, anti-TB, antimalarial, antiviral, anti-HIV, and many other uses. Variously substituted quinoxalines are significant therapeutic agents in the pharmaceutical industry. This review spotlights on the ch

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6

Mohamed, Hanan A., Mohammad Hayal Alotaibi, Benson M. Kariuki, and Gamal A. El-Hiti. "Convenient Synthesis of New Heterocycles Containing the Quinoxaline Ring System." Letters in Organic Chemistry 17, no. 2 (2020): 121–26. http://dx.doi.org/10.2174/1570178616666190311161505.

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: The aim of the current article was to describe simple procedures for the synthesis of new heterocycles incorporating the quinoxaline moiety using benzene-1,2-diamine and quinoxaline-2,3- dithiol as precursors. Simple synthetic methods are described for the synthesis of new heterocycles using commercially available chemicals. Also, the new compounds were determined using analytical and spectroscopic methods including single X-ray crystal structures. A series of new heterocycles containing the quinoxaline nucleus have been synthesized in good yields using simple and convenient procedures. A pr

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7

Wang, Cui-Ping, Saiyong Ma, Jiang-Long Yu, Jing-Bo Yan, and Zhi-Qiang Zhang. "2-(4-Fluorophenyl)quinoxaline." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1779. http://dx.doi.org/10.1107/s1600536812017771.

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In the title compound, C14H9FN2, the dihedral angle between the benzene ring and the quinoxaline ring system is 22.2 (3)°. Any aromatic π–π stacking in the crystal must be very weak, with a minimum centroid–centroid separation of 3.995 (2) Å.

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8

Montero, Vincent, Marc Montana, Omar Khoumeri, Florian Correard, Marie-Anne Estève, and Patrice Vanelle. "Synthesis, In Vitro Antiproliferative Activity, and In Silico Evaluation of Novel Oxiranyl-Quinoxaline Derivatives." Pharmaceuticals 15, no. 7 (2022): 781. http://dx.doi.org/10.3390/ph15070781.

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The quinoxaline core is a promising scaffold in medicinal chemistry. Multiple quinoxaline derivatives, such as the topoisomerase IIβ inhibitor XK-469 and the tissue transglutaminase 2 inhibitor GK-13, have been evaluated for their antiproliferative activity. Previous work reported that quinoxaline derivatives bearing an oxirane ring present antiproliferative properties against neuroblastoma cell lines SK-N-SH and IMR-32. Likewise, quinoxalines with an arylethynyl group displayed promising antineoplastic properties against glioblastoma and lung cancer cell lines, U87-MG and A549 respectively. H

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9

Ouyang, Xi-Lin, Miao Ouyang, and Shi-Wen Huang. "6-Chloro-2-phenyl-3-(2-phenylethynyl)quinoxaline." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1741. http://dx.doi.org/10.1107/s1600536812020776.

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In the title compound, C22H13ClN2, the quinoxaline ring system is close to planar [maximum deviation = 0.061 (2) Å]. The phenyl ring at the 2-position and the phenyl ring of the phenylethynyl substituent make dihedral angles of 49.32 (7) and 11.99 (7) °, respectively, with the quinoxaline mean plane. The two phenyl rings are inclined to one another by 61.27 (9)°. In the crystal, molecules are linked by C—H...π and π–π interactions [centroid–centroid distances = 3.6210 (12) and 3.8091 (12) Å].

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10

Elgogary, Sameh R., and Emad M. El-Telbani. "Synthesis of tricyclic fused quinoxaline ring systems: Isoxazolo-, oxazolo-, isothiazolo- and thiazoloquinoxalines (a review)." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 263. https://doi.org/10.59467/ijhc.2025.35.263.

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Quinoxaline derivatives have gained great interest because they exhibit a variety of pharmacological activities, including antibacterial, antitubercular, antiviral, anti-HIV, anti-inflammatory, antifungal, anticancer, antiproliferative, antitumor, kinase inhibition, antimicrobial, antioxidant, and analgesic effects. Recognizing the importance of these bioactive quinoxaline derivatives, researchers have dedicated their efforts to develop different synthetic routes for their production. This review aims to compile the most recent findings on the synthesis of quinoxaline derivatives incorporating

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11

Sharma, Aastha, Aakash Deep, Minakshi Gupta Marwaha, and Rakesh Kumar Marwaha. "Quinoxaline: A Chemical Moiety with Spectrum of Interesting Biological Activities." Mini-Reviews in Medicinal Chemistry 22, no. 6 (2022): 927–48. http://dx.doi.org/10.2174/1389557521666210927123831.

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Abstract: Quinoxaline (C8H6N2), commonly called 1,4-diazanaphthalene, 1,4-benzodiazine, or benzopyrazine, is a very potent nitrogenous heterocyclic moiety consisting of a benzene ring fused with the pyrazine ring. A number of different methods for the synthesis of quinoxaline derivatives have been reported in the literature, but the most effective method, commonly used for the synthesis of quinoxaline analogues involves the condensation of substituted o-phenylenediamines with 1, 2- dicarbonyl compounds in the presence of different catalyst(s). The presence of different types of catalysts and t

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12

Schramm, Frank, Dirk Walther, Helmar Görls, Christian Käpplinger, and Rainer Beckert. "Trifluoromethylaryl-Substituted Quinoxalines: Unusual Ruthenium- Amidininate Complexes and their Suitability for Anellation Reactions." Zeitschrift für Naturforschung B 60, no. 8 (2005): 843–52. http://dx.doi.org/10.1515/znb-2005-0805.

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The reaction of the 2,3-dianilino-quinoxaline 1 with an equivalent of triethyl orthoformiate results in a cyclic aminalester 2. An excess of triethyl orthoformate results in the carbene dimer 4. With the help of boron trifluoride, 2 can be transformed into the imidazolium salt 3. Reaction of 1 with KOtC4H9 leads to a quinoxaline derivative 5 under anellation of a benzene ring whereas the related pyrazino-quinoxaline 6 (formed from tetraaminobenzene tetrahydrochloride and bis-(3- trifluoromethylphenyl) oxalimidoyl chloride) does not react under similar conditions. However, 6 can be activated to

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13

Hoffman, Gavin R., and Allen M. Schoffstall. "Syntheses and Applications of 1,2,3-Triazole-Fused Pyrazines and Pyridazines." Molecules 27, no. 15 (2022): 4681. http://dx.doi.org/10.3390/molecules27154681.

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Pyrazines and pyridazines fused to 1,2,3-triazoles comprise a set of heterocycles obtained through a variety of synthetic routes. Two typical modes of constructing these heterocyclic ring systems are cyclizing a heterocyclic diamine with a nitrite or reacting hydrazine hydrate with dicarbonyl 1,2,3-triazoles. Several unique methods are known, particularly for the synthesis of 1,2,3-triazolo[1,5-a]pyrazines and their benzo-fused quinoxaline and quinoxalinone-containing analogs. Recent applications detail the use of these heterocycles in medicinal chemistry (c-Met inhibition or GABAA modulating

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14

Srinivasan, T., S. Suhitha, S. Purushothaman, R. Raghunathan, and D. Velmurugan. "{1′-Phenyl-1′,2′,5′,6′,7′,7a'-hexahydrospiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizin]-2′-yl}(p-tolyl)methanone." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2469. http://dx.doi.org/10.1107/s1600536812031480.

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In the title compound, C35H29N3O, the quinoxaline and indene systems are essentially planar, with maximum deviations of 0.047 (2) and 0.032 (2) Å for C atoms, respectively. The quinoxaline system forms a dihedral angle of 4.75 (3)° with the indene system. The pyrrolizine system is folded. The substituted five-membered ring adopts an envelope conformation. In the other five-membered ring, one C atom is disordered with a site-occupancy ratio of 0.676 (12):0.324 (12). In the crystal, molecules are linkedviaC—H...O hydrogen bonds involving the bifurcated carbonyl O atom.

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15

Lu, Tong, Ling Dong, Hongmei Pan, et al. "Design and synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives via click reactions." Journal of Chemical Research 44, no. 11-12 (2020): 699–704. http://dx.doi.org/10.1177/1747519820919853.

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The synthesis of C-ring quinoxaline-substituted sinomenine 1,2,3-triazole derivatives at the 4-OH via click reactions is accomplished, and a total of 16 novel sinomenine double N-heterocyclic derivatives are obtained in 74%–95% yields. The C-ring is first transformed into a 1,2-diketone structure under the action of hydrochloric acid, and then reacted with o-phenylenediamine to obtain a C-ring quinoxaline-substituted structure. The 4-OH of sinomenine reacts with chloropropyne to give an alkynyl sinomenine, and then reacts with sodium azide and various benzyl chlorides to give the target compou

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16

Nagalakshmi, R. A., J. Suresh, K. Malathi, R. Ranjith Kumar, and P. L. Nilantha Lakshman. "Crystal structure of 1′,1′′-dimethyl-4′-(4-cholorophenyl)dispiro[11H-indeno[1,2-b]quinoxaline-11,2′-pyrrolidine-3′,3′′-piperidin]-4′′-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 2 (2015): o68—o69. http://dx.doi.org/10.1107/s2056989014027698.

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In the title compound, C30H27ClN4O, the central pyrrolidine ring adopts an envelope conformation with the methylene C atom being the flap. The quinoxaline and indane rings are each essentially planar, with r.m.s. deviations of 0.027 (1) and 0.0417 (1) Å, respectively. The pyrrolidine ring forms dihedral angles of 88.25 (1) and 83.76 (1)° with the quinoxaline and indane rings, respectively. A weak intramolecular C—H...N interaction is observed. In the crystal, C—H...π interactions lead to supramolecular chains along [101] that assemble in theacplane. Connections along thebaxis are of the type C

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17

Tauer, Erich, and Karl-Heinz Grellmann. "Photochemical Dehydrogenation, Ring Contraction, and Ring Expansion of Hydrogenated Derivatives of Benzoxazino-benzoxazine, Quinoxalino-quinoxaline, and Bibenzothiazole." Chemische Berichte 123, no. 5 (1990): 1149–54. http://dx.doi.org/10.1002/cber.19901230531.

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18

Wickham, Laura M., Joseph M. Tanski, and Jocelyn M. Nadeau. "Crystal structure of a fluorescent C-shaped molecule containing closely stacked bithiophene-substituted quinoxaline rings." Acta Crystallographica Section C Structural Chemistry 73, no. 3 (2017): 276–79. http://dx.doi.org/10.1107/s2053229617001991.

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Molecules with well-defined structures that feature closely stacked aromatic rings are important for understanding π–π interactions. A previously reported C-shaped molecule with bithiophene-substituted quinoxaline rings suspended from an aliphatic bridge that holds the aromatic rings in close proximity exists as a pair of syn and anti diastereomers. The anti isomer, namely (1α,2β,4β,5α,16α,17β,19β,20α)-1,5,16,20-tetrachloro-31,31,32,32-tetramethoxy-11,26-bis[5-(thiophen-2-yl)thiophen-2-yl]-7,14,22,29-tetraazanonacyclo[18.10.1.15,16.02,19.04,17.06,15.08,13.021,30.023,28]dotriaconta-6(15),7,9,11

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19

Singh, Ruby, Diksha Bhardwaj, and Munna Ram Saini. "Recent advancement in the synthesis of diverse spiro-indeno[1,2-b]quinoxalines: a review." RSC Advances 11, no. 8 (2021): 4760–804. http://dx.doi.org/10.1039/d0ra09130h.

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20

Castillo, Juan C., Rodrigo Abonía, Justo Cobo та Christopher Glidewell. "A chain of π-stacked molecules in 4-(2-chlorophenyl)pyrrolo[1,2-a]quinoxaline and a hydrogen-bonded sheet in (4RS)-4-(1,3-1,3-benzodioxol-6-yl)-4,5-dihydropyrrolo[1,2-a]quinoxaline". Acta Crystallographica Section C Crystal Structure Communications 69, № 5 (2013): 544–48. http://dx.doi.org/10.1107/s0108270113009098.

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In the molecule of 4-(2-chlorophenyl)pyrrolo[1,2-a]quinoxaline, C17H11ClN2, (I), the bond lengths are consistent with electron delocalization in the two outer rings of the fused tricyclic system, with a localized double bond in the central ring. The molecules of (I) are linked into chains by a π–π stacking interaction. In (4RS)-4-(1,3-benzodioxol-6-yl)-4,5-dihydropyrrolo[1,2-a]quinoxaline, C18H14N2O2, (II), the central ring of the fused tricyclic system adopts a conformation intermediate between screw-boat and half-chair forms. A combination of N—H...O and C—H...π(arene) hydrogen bonds links t

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21

Qiao, Zi, Meng Wang, Mingzhi Zhao, et al. "Effect of fluorine substitution on the photovoltaic performance of poly(thiophene-quinoxaline) copolymers." Polymer Chemistry 6, no. 47 (2015): 8203–13. http://dx.doi.org/10.1039/c5py01193k.

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22

Forsyth, Craig M., and Craig L. Francis. "Crystal structures of two 2,3-diethylnaphtho[2,3-g]quinoxaline-6,11-dione derivatives." Acta Crystallographica Section E Crystallographic Communications 73, no. 8 (2017): 1125–29. http://dx.doi.org/10.1107/s2056989017009641.

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Two new 5,12-disubstituted 2,3-diethylnaphtho[2,3-g]quinoxaline-6,11-dione compounds were readily synthesized from the commercial dye quinizarin. For 2,3-diethyl-5,12-dihydroxynaphtho[2,3-g]quinoxaline-6,11-dione, (II), C20H16N2O4, the molecule displays a near planar conformation and both hydroxy groups participate in intramolecular O—H...O(carbonyl) hydrogen bonds. In the crystal, π–π ring interactions [minimum ring centroid separation = 3.5493 (9) Å] form stacks of co-planar molecules down the c axis, while only minor intermolecular C—H...O interactions are present. In contrast, in 2,3-dieth

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23

Plater, Michael John, and William T. A. Harrison. "Stereoview Images of Hydrogen-Bonded Quinoxalines with a Helical Axis; Pyrimidines and a Pyridazine That Form Extended Tapes." International Journal of Molecular Sciences 25, no. 22 (2024): 12329. http://dx.doi.org/10.3390/ijms252212329.

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Different supramolecular motifs are formed by the crystallisation of amino-substituted derivatives of quinoxaline, pyrimidine and pyridazine. These were made from the corresponding mono- or dichlorinated heterocycles by a nucleophilic displacement reaction. The pyridine-type nitrogen atoms activate the chlorine atoms because they can stabilise a negative charge, which forms when the amine attacks the ring. One amino group can be attached under mild conditions in hot ethanol or acetonitrile, but the first then deactivates the ring so the second requires more forceful conditions using a pressure

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24

Umesh, Verma* Poonam Rishishwar Sanjay Rishishwar. "A State-Of-The-Art Overview of Quinoxaline, Its Derivatives, and Applications." International Journal of Pharmaceutical Sciences 3, no. 4 (2025): 1337–58. https://doi.org/10.5281/zenodo.15193134.

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A significant type of heterocycle molecules are quinoxaline derivatives, in which N substitutes for some of the carbon atoms in the naphthalene ring. It is made up of the fusion of two aromatic rings, pyrazine and benzene, and has the chemical formula C8H6N2. Although it is uncommon in nature, it is simple to synthesize them. The State of the Art will be discussed in this review, along with an overview of the advancements in understanding the structure and mechanism of quinoxaline and its derivatives, as well as their related industrial, medicinal, and biological importance. Numerous biomedica

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25

Montana, Marc, Vincent Montero, Omar Khoumeri, and Patrice Vanelle. "Quinoxaline Moiety: A Potential Scaffold against Mycobacterium tuberculosis." Molecules 26, no. 16 (2021): 4742. http://dx.doi.org/10.3390/molecules26164742.

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Background. The past decades have seen numerous efforts to develop new antitubercular agents. Currently, the available regimens are lengthy, only partially effective, and associated with high rates of adverse events. The challenge is therefore to develop new agents with faster and more efficient action. The versatile quinoxaline ring possesses a broad spectrum of pharmacological activities, ensuring considerable attention to it in the field of medicinal chemistry. Objectives. In continuation of our program on the pharmacological activity of quinoxaline derivatives, this review focuses on poten

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26

Jigajinni, V. B., P. N. Preston, V. K. Shah, S. W. Simpson, I. Soutar, and N. J. Stewart. "Structure-property relationships in PMR-15-type polyimide resins: IIH. New polyimides incorporating triazoles, quinoxalines, pyridopyrazines and pyrazinopyridazines." High Performance Polymers 5, no. 3 (1993): 239–57. http://dx.doi.org/10.1088/0954-0083/5/3/008.

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Polyimide oligomers (prepolymers) and resins of the PMR-15 type have been prepared from 5-norbomene-2,3-dicarboxylic half acid ester (NE), 3,3',4,4'-benzophenone tetracarboxylic diester (BTDE) and a series of diamines incorporating 1,2,3-triazole, quinoxaline, pyrido[2,3-b]pyrazine, pyrido[3,4-b]pyrazine, benzo[g]quinoxaline, pyrazino-[2,3]-d]pyridazine and bis(pyrido[3,4-b]pyrazino)benzene ring systems. Two tetraamines in the bis(pyrazino[2,3-d]pyridazino)benzene ring system were also employed. Selected diamine monomers from the above ring systems provde PMR-15-analogue resins of higher therm

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27

Boraei, Ahmed T. A., Ahmed A. M. Sarhan, Sammer Yousuf, and Assem Barakat. "Synthesis of a New Series of Nitrogen/Sulfur Heterocycles by Linking Four Rings: Indole; 1,2,4-Triazole; Pyridazine; and Quinoxaline." Molecules 25, no. 3 (2020): 450. http://dx.doi.org/10.3390/molecules25030450.

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A new series of nitrogen and sulfur heterocyclic systems were efficiently synthesized by linking the following four rings: indole; 1,2,4-triazole; pyridazine; and quinoxaline hybrids. The strength of the acid that catalyzes the condensation of 4-amino-5-(1H-indol-2-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thione 1 with aromatic aldehydes controlled the final product. Reflux in glacial acetic acid yielded Schiff bases 2–6, whereas concentrated HCl in ethanol resulted in a cyclization product at C-3 of the indole ring to create indolo-triazolo-pyridazinethiones 7–16. This fascinating cyclization appr

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28

Koch, Pierre, Dieter Schollmeyer, and Stefan Laufer. "4-[3-(4-Fluorophenyl)quinoxalin-2-yl]-N-isopropylpyridin-2-amine." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): o1344. http://dx.doi.org/10.1107/s1600536809018285.

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In the crystal structure of the title compound, C22H19FN4, the quinoxaline system makes dihedral angles of 32.07 (13) and 69.64 (13)° with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 71.77 (16)° with the pyridine ring. The crystal structure is stabilized by intermolecular N—H...N hydrogen bonding.

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29

Jang, Chun Keun, Cheol Jun Song, Wang Yao, Ki Hoon Jang, and Jae Yun Jaung. "Optical Sensitivity of Electrospun Fibers Containing Quinoxalines Derived with Metal Ion Chelating Agent." Advanced Materials Research 314-316 (August 2011): 112–18. http://dx.doi.org/10.4028/www.scientific.net/amr.314-316.112.

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Fluorescent chromophores are generally known to have planar and rigid -conjugation systems, and we have been interested in the chemistry of nitrogen-containing heterocyclic molecules for many years. Quinoxaline was the representative fluorophore, and several quinoxaline derivative compounds were reported over the recent years. Quinoxaline can easily change their absorption or emission wavelength by oxidation among proton and nitrogen of the quinoxaline ring. In addition, it has been proved that many types of metal chelating ligand substituents such as dipyrrole, terpyridine, and crown-ether r

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30

Zhang, Jinpeng, Yinan Wang, Qian Wang, and Lichun Xu. "6,7-Dichloro-3-(2,4-dichlorobenzyl)quinoxalin-2(1H)-one." Acta Crystallographica Section E Structure Reports Online 68, no. 8 (2012): o2481. http://dx.doi.org/10.1107/s160053681203098x.

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In the title compound, C15H8Cl4N2O, the quinoxaline ring system is almost planar, with a dihedral angle between the benzene and pyrazine rings of 3.1 (2)°. The 2,4-dichlorophenyl ring is approximately perpendicular to the pyrazine ring, with a dihedral angle of 86.47 (13)° between them. The crystal packing features intermolecular N—H...O hydrogen bonds and π–π stacking interactions, with centroid–centroid distances in the range 3.699 (3)–4.054 (3) Å.

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31

Corona, Paola, Stefania Gessi, Roberta Ibba, et al. "Novel Oxadiazole-Quinoxalines as Hybrid Scaffolds with Antitumor Activity." International Journal of Molecular Sciences 26, no. 4 (2025): 1439. https://doi.org/10.3390/ijms26041439.

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A small library of 25 novel 1,3,4-oxadiazole-quinoxalines was synthesized and evaluated in vitro for its cytotoxic activity at 10 μM concentration against nine NCI-different cancer cell lines. Among tested compounds, derivatives 24, 25, and 26 showed good inhibition percentages over different cell lines and, therefore, progressed to the full five-dose assay. Compound 24, possessing a 1,3,4-oxadiazole-core, bearing a 7-trifluoromethyl-quinoxaline nucleus on C-2 and a C-5 phenyl ring, had activity against leukemia, CNS, ovarian, renal, prostate, and breast cancer, with highest the values against

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32

Kudrevich, Svetlana V., Johan E. Van Lier, Maria G. Galpern, and Evgeny A. Luk'yanets. "Substituted tetra-2,3-pyrazinoporphyrazines. Part I. Angular annelation of tetra-2,3-quinoxalinoporphyrazine." Canadian Journal of Chemistry 74, no. 4 (1996): 508–15. http://dx.doi.org/10.1139/v96-055.

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Several derivatives of 2,3-dicyanopyrazine were prepared via the condensation of o-quinones with diaminomaleodinitrile. Benzo[f]quinoxaline-2,3-dinitrile was obtained from 1,2-naphthoquinone, and a series of isomeric, di-tert-butyl substituted 5,6-(9,10-phenanthro)-2,3-dicyanopyrazines were prepared from the corresponding di-tert-butyl-9,10-phenanthrenequinones. Complexation of benzo[f]quinoxaline-2,3-dinitrile, and unsubstituted 5,6-(9,10-phenanthro)-2,3-dicyanopyrazine, with an appropriate metal salt yielded metal complexes of tetra-2,3-(benzo[f]quinoxalino)porphyrazine and tetra-2,3-[5,6-(9

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Gotoh, Kazuma, Hirokazu Nagoshi, and Hiroyuki Ishida. "Quinoxaline–chloranilic acid (1/1)." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (2007): o4295. http://dx.doi.org/10.1107/s1600536807049483.

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In the crystal structure of the title compound, C8H6N2·C6H2Cl2O4, there are two crystallographically independent chloranilic acid (systematic name: 2,5-dichloro-3,6-dihydroxy-1,4-benzoquinone) molecules, each of which is located on an inversion center. The quinoxaline ring system makes dihedral angles of 6.09 (9) and 44.50 (9)° with the two chloranilic acid planes. The quinoxaline and the chloranilic acid are connected alternately by O—H...N hydrogen bonds, forming a zigzag chain running along the [20\overline{1}] direction. The chains are stacked along the a axis, forming a layer extending pa

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34

Boguslavskii, A. M., M. G. Ponizovskii, M. I. Kodess, and V. N. Charushin. "Ring-Chain Transformations of Dihydroisoxazolo[4,5-b]quinoxaline." Russian Journal of Organic Chemistry 41, no. 9 (2005): 1377–80. http://dx.doi.org/10.1007/s11178-005-0350-4.

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35

Wang, Wei, Ning-Ning Pan, and Bing Zhao. "2,3-Bis[(1-phenyl-1H-tetrazol-5-ylsulfanyl)methyl]quinoxaline." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): o2817—o2818. http://dx.doi.org/10.1107/s1600536806021659.

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The title compound, C24H18N10S2, crystallizes with two independent molecules in the asymmetric unit. The two terminal (1-phenyltetrazol-5-yl)sulfanyl groups adopt a trans configuration with respect to the central quinoxaline ring system in both independent molecules.

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36

Bobokhidze, Lia. "NOVEL SYNTHETIC INVESTIGATION IN THE FIELD OF INDOLO[2,3-B]QUINOXALINE RING CONTAINING TETRACYCLIC AND PENTACYCLIC HETEROCYCLES." New Materials, Compounds and Applications 8, no. 1 (2024): 13–23. http://dx.doi.org/10.62476/nmca8113.

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A series of seven new indolo[2,3-b]quinoxaline ring containing compounds were efficiently synthesized in three different pathways. In the first case, the relevant pentacyclic systems (3,4) were received by the condensation reaction between 7-acetyl-1,5,6,7-tetrahydropyrrolo[3,2-f]indole-2,3-dione and o-phenylenediamine in glacial acetic acid. In the second case, tetracyclic indolo[2,3-b]qui-no¬xa¬li¬ne derivatives (7, 8a-d) were synthesised by a one-pot approach using Pd-catalyzed Sonogashira-hagihara C-C cross-coupling reaction between various terminal acetylenes and 9-iodo-6H-indo¬lo¬[2,3-b]

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37

Oda, Tomohiro, Yuina Onishi, Akihito Konishi, and Makoto Yasuda. "Synthesis and Characterization of Quinoxaline-Fused Cyclopenta[cd]azulene." Chemistry 7, no. 1 (2025): 15. https://doi.org/10.3390/chemistry7010015.

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Azulene-based polycyclic hydrocarbons have garnered much attention as potential materials for organic optoelectronic devices and as molecular models for graphene nanosheets with structural defects. Although various methods for ring fusions to an azulene core have been established for ring fusions to an azulene core, efficient synthetic methodologies for ortho- and peri-fusion to an azulene core are still lacking, which hinders the investigation of the effect of the ortho- and peri-fusion on the electronic properties of the embedded azulene core. Herein, we describe the synthesis and characteri

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38

Singh, Praphulla kumar, and Babu Nand Choudhary. "Exploring Novel Quinoxaline Derivatives as Potent Antiviral Agents: Synthesis and Biological Insights." Journal of Biochemistry International 12, no. 1 (2025): 57–69. https://doi.org/10.56557/jobi/2025/v12i19217.

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The present study explores about synthesis and biological Insights of Novel Quinoxaline Derivatives as Potent Antiviral Agents. Viral infections are a big public health issue and we need antiviral agents. There has been a surge in interest regarding quinoxaline derivatives during recent years owing to the large array of therapeutic qualities they possess. A variety of analyses conducted between the years 2020 to 2024 have proved to be useful for any biological application including anticancer, antimicrobial, antiviral, anti-inflammatory and even antidiabetic. Due to their ability to treat a wi

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39

KASORNMALA, Kamonrat, Vittaya AMORNKITBAMRUNG, and Pornjuk SREPUSHARAWOOT. "Effects of Organic Linkers on Energy gaps of Covalent based Triazine Frameworks." Walailak Journal of Science and Technology (WJST) 15, no. 11 (2018): 811–17. http://dx.doi.org/10.48048/wjst.2018.5966.

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The Covalent Triazine Frameworks (CTFs) were successfully synthesized from the experiments. They usually consist of triazine ring covalently bonded with organic linkers. CTF-Benzene was defined in case of the organic linker be benzene ring. Moreover, 5 different types of organic linkers, namely, Napthalene, Quinoline, Quinoxaline, Anthracene and Acridine were chosen to connect to the boroxine ring and these structures are abbreviated as CTF-Naphthalene, CTF-Quinoline, CTF-Quinoxaline, CTF-Anthracene and CTF-Acridine, respectively. In the present study, the structural parameters, the density of

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Matsumoto, Shoji, Makoto Takamori, and Motohiro Akazome. "Bathochromic Shift of Fluorescence Peak in Dipyrrolo[1,2-a:2′,1′-c]quinoxaline by Introducing Each of Electron-Donating and Electron-Withdrawing Substituent." Molecules 28, no. 7 (2023): 2896. http://dx.doi.org/10.3390/molecules28072896.

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Development of organic fluorophore is an important theme. Especially, the fluorophores with longer fluorescence peaks are useful to biological probes. One of the methods to change the fluorescence peak is the introduction of substituents. However, opposing characteristics of the substituents lead to different changes in the fluorescence peaks. Furthermore, the introduction of the substituent also affects their electric properties. Thus, if the materials were developed with the substituent effect on the optical and electric properties separately, it will be useful to design the functional mater

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Jeon, Youngeun, Jineun Kim, Sangjin Lee, and Tae Ho Kim. "Crystal structure of propaquizafop." Acta Crystallographica Section E Structure Reports Online 70, no. 12 (2014): o1266—o1267. http://dx.doi.org/10.1107/s1600536814024751.

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The title compound, C22H22ClN3O5{systematic name: 2-(propan-2-ylideneaminooxy)ethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate}, is a herbicide. The asymmetric unit comprises two independent molecules in which the dihedral angles between the phenyl ring and the quinoxaline ring plane are 75.93 (7) and 82.77 (8)°. The crystal structure features C—H...O, C—H...N, and C—H...Cl hydrogen bonds, as well as weak π–π interactions [ring-centroid separation = 3.782 (2) and 3.5952 (19) Å], resulting in a three-dimensional architecture.

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42

Armand, Joseph, Line Boulares, Christian Bellec, and Jean Pinson. "Preparation, chemical and electrochemical reduction of pyrido[2,3-b]quinoxalines and pyrido[3,4-b]quinoxalines." Canadian Journal of Chemistry 66, no. 6 (1988): 1500–1505. http://dx.doi.org/10.1139/v88-242.

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The reaction of 2,3-diaminopyridine with the dimeric 4,5-dimethylcyclohexa-3,5-dien-1,2-dione gives 7,8-dimethylpyrido[2,3-b]quinoxaline, 1, in good yields; in the same way 3,4-diaminopyridine gives the 7,8-dimethylpyrido[3,4-b]quinoxaline 2. The electrochemical reduction of 1 and 2 in hydroorganic medium gives the 5,10-dihydro compounds 6 and 7; 1 and 2 present a single 2e− polarographic wave, in contrast to phenazine which shows two monoelectronic waves. The catalytic hydrogenation of 1 and 2 gives 6 and 7 and does not involve the pyridinic ring as in the case of pyridopyrazines. AlLiH4 does

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43

Yahcoob, Nehla, Baskar Lakshmanan, Jyothi Achuthanandhan, and Vijayakumar Balakrishnan. "In-silico screening of 2,3-diphenylquinozaline derivatives as C-met kinase inhibitors." JOURNAL OF PHARMACEUTICAL CHEMISTRY 4, no. 3 (2017): 41–45. http://dx.doi.org/10.14805/jphchem.2017.art84.

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Quinoxaline, an important class of heterocylic compounds drawn greater attention due to their wide spectrum of biological activities. They are considered as an important chemical scaffold for anticancer drug design due to their potential inhibitory activity against C-met tyrosine kinase. C-met kinase inhibitors are a class of small molecules that having therapeutic potential in the treatment of various types of cancers. The present study aims to focus on the chemistry of quinoxaline derivatives, their potential activities against C-met tyrosine kinase, and in-silico screening of designed compo

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44

Volovenko, Yu M., S. V. Litvinenko, and F. S. Babichev. "Annelation of the benzindolizine ring to the quinoxaline nucleus." Chemistry of Heterocyclic Compounds 25, no. 11 (1989): 1317–18. http://dx.doi.org/10.1007/bf00481538.

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45

Barbosa-Cabrera, Elizabeth, Rosa Moo-Puc, Antonio Monge, Alma Delia Paz-González, Virgilio Bocanegra-García, and Gildardo Rivera. "In vitro and In Vivo Evaluation of Quinoxaline 1,4-di-N-oxide Against Giardia lamblia." Letters in Drug Design & Discovery 17, no. 4 (2020): 428–33. http://dx.doi.org/10.2174/1570180816666190618115854.

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Background: Giardiasis is an important public health problem. However, its pharmacological treatment is limited mainly to two drugs, metronidazole and nitazoxanide. Objectives: Screening four series of esters (methyl, ethyl, isopropyl and n-propyl) of quinoxaline-7- carboxylate 1,4-di-N-oxide in in vitro and in vivo models as antigiardiasis agents. Objectives: Screening four series of esters (methyl, ethyl, isopropyl and n-propyl) of quinoxaline-7- carboxylate 1,4-di-N-oxide in in vitro and in vivo models as antigiardiasis agents. Methods: Briefly, 4 × 104 trophozoites of G. lamblia were incub

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46

Govindaraj, J., R. Raja, M. Suresh, R. Raghunathan, and A. SubbiahPandi. "Crystal structure of ethyl (2S,2′R)-1′-benzyl-3-oxo-3H-dispiro[1-benzothiophene-2,3′-pyrrolidine-2′,11′′-indeno[1,2-b]quinoxaline]-4′-carboxylate." Acta Crystallographica Section E Crystallographic Communications 71, no. 3 (2015): o195—o196. http://dx.doi.org/10.1107/s2056989015003187.

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In the title compound, C35H27N3O3S, the spiro-linked five-membered rings both adopt twisted conformations. The pyrrolidine ring makes dihedral angles of 80.5 (1) and 77.4 (9)° with the benzothiophene ring system and the quinoxaline ring system, respectively. The S atom and C=O unit of the benzothiophene ring system are disordered over two opposite orientations in a 0.768 (4):0.232 (4) ratio. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.680 (16):0.320 (16) ratio. In the crystal, molecules are linked by C—H...O, C—H...N and π–π interactions [shortest centroid–ce

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47

Buravchenko, Galina I., Dmitry A. Maslov, Md Shah Alam, et al. "Synthesis and Characterization of Novel 2-Acyl-3-trifluoromethylquinoxaline 1,4-Dioxides as Potential Antimicrobial Agents." Pharmaceuticals 15, no. 2 (2022): 155. http://dx.doi.org/10.3390/ph15020155.

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The emergence of drug resistance in pathogens leads to a loss of effectiveness of antimicrobials and complicates the treatment of bacterial infections. Quinoxaline 1,4-dioxides represent a prospective scaffold for search of new compounds with improved chemotherapeutic characteristics. Novel 2-acyl-3-trifluoromethylquinoxaline 1,4-dioxides with alteration of substituents at position 2 and 6 were synthesized via nucleophilic substitution with piperazine moiety and evaluated against a broad panel of bacteria and fungi by measuring their minimal inhibitory concentrations. Their mode of action was

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48

Bhattarai, Shambhu, Pradeep Mareta, Philip W. Crawford, Jonathan M. Kessler, and Christina M. Ragain. "Improved Computational Prediction of the Electrochemical Reduction Potential of Twenty 3-Aryl-Quinoxaline-2-Carbonitrile 1,4-Di-N-Oxide Derivatives." Computation 11, no. 1 (2023): 9. http://dx.doi.org/10.3390/computation11010009.

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The ability of density functional theory (DFT) using the functional B3LYP with the cc-pVTZ basis set to accurately predict the electrochemical properties of 20 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives in dimethylformamide (DMF) was investigated and compared to previous predictions from B3LYP/6-31G and B3LYP/lanl2dz. The B3LYP/cc-pVTZ method was an improvement over the B3LYP/6-31G and B3LYP/lanl2dz methods as it was able to predict the first reduction potential of the diazine ring (wave 1) for all of the 3-aryl-quinoxaline-2-carbonitrile 1,4-di-N-oxide derivatives accurately

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49

Kim, Young-Inn, Seong-Jae Yun, and Sung Kwon Kang. "Crystal structure of 2,3-bis(4-methylphenyl)benzo[g]quinoxaline." Acta Crystallographica Section E Crystallographic Communications 74, no. 4 (2018): 548–50. http://dx.doi.org/10.1107/s2056989018004413.

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The title compound, C26H20N2, was obtained during a search for new π-extended ligands with the potential to generate efficient phosphors with iridium(III) for organic light-emitting devices (OLEDs). The benzoquinoxaline ring system is almost planar (r.m.s. deviation = 0.076 Å). A pseudo-twofold rotation axis runs through the midpoints of the C2—C3 and C9—C10 bonds. The two phenyl rings are twisted relative to the benzoquinoxaline ring system, making dihedral angles of 53.91 (4) and 36.86 (6)°. In the crystal, C—H...π (arene) interactions link the molecules, but no π–π interactions between arom

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50

Chrysochos, Nicolas, and Carola Schulzke. "Crystal structure of 1-ethyl-3-(2-oxo-1,3-dithiol-4-yl)quinoxalin-2(1H)-one." Acta Crystallographica Section E Crystallographic Communications 74, no. 7 (2018): 901–4. http://dx.doi.org/10.1107/s2056989018007892.

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The title compound I, C13H10N2O2S2, crystallizes in the monoclinic space group C2/c with eight molecules in the unit cell. Excluding for the ethyl substituent, the molecule of I adopts a nearly coplanar conformation (r.m.s. deviations is 0.058 Å), which is supported by the intramolecular C—H...O hydrogen-bonding interaction between the two ring systems [C...O = 2.859 (3) Å]. In the crystal, the molecules form dimeric associates via two bifurcated C—H...O hydrogen-bonding interactions between an ene hydrogen atom and a carbonyl functional group of an adjacent molecule [C...O = 3.133 (3) Å] and

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