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Journal articles on the topic 'Pyrrolo[2,3-b]quinoxaline'

Author: Grafiati

Published: 24 April 2022

Last updated: 30 July 2025

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1

Sadykhov, Gusein A., Danila V. Belyaev, Ekaterina E. Khramtsova, et al. "4-Alkyl-4H-thieno[2′,3′:4,5]pyrrolo[2,3-b]quinoxaline Derivatives as New Heterocyclic Analogues of Indolo[2,3-b]quinoxalines: Synthesis and Antitubercular Activity." International Journal of Molecular Sciences 26, no. 1 (2025): 369. https://doi.org/10.3390/ijms26010369.

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The synthetic approach based on a sequence of Buchwald–Hartwig cross-coupling and annulation through intramolecular oxidative cyclodehydrogenation has been used for the construction of novel 4-alkyl-4H-thieno[2′,3′:4,5]pyrrolo[2,3-b]quinoxaline derivatives. For the first time, these polycyclic compounds were evaluated for antimycobacterial activity, including extensively drug-resistant strains. A reasonable bacteriostatic effect against Mycobacterium tuberculosis H37Rv was demonstrated. A plausible mechanism for antimycobacterial activity of heterocyclic analogues of indolo[2,3-b]quinoxalines

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2

Iranfar, Sheiva, Morteza Shiri, Yazdanbakhsh Lotfi Nosood, et al. "An efficient and practical approach for the synthesis of indoloquinolines and indolo/pyrroloquinoxalines via a Cu-catalyzed Ugi-C/Ugi-N-arylation sequence." RSC Advances 14, no. 26 (2024): 18271–76. http://dx.doi.org/10.1039/d4ra03248a.

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A Cu-catalyzed tandem transformation of Ugi adducts through CH/NH bond functionalization reactions was reported for synthesizing a broad spectrum of indolo/pyrrolo-[1,2-a]quinoxaline and indolo[2,3-c]quinoline derivatives in good to excellent yields.

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3

Moghaddam, Firouz Matloubi, Atiyeh Moafi, Behzad Jafari, Alexander Vilinger, and Peter Langer. "Regio- and Diastereoselective Synthesis of Novel Polycyclic Pyrrolo[2,1-a]isoquinolines Bearing Indeno[1,2-b]quinoxaline Moieties by a Three-Component [3+2]-Cycloaddition Reaction." Synlett 31, no. 03 (2019): 267–71. http://dx.doi.org/10.1055/s-0039-1690768.

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A regio- and diastereoselective synthesis of 2,3-dihydro-10b′H-spiro[indeno[1,2-b]quinoxaline-11,1′-pyrrolo[2,1-a]isoquinoline]-2′,3′-diylbis(phenylmethanone) derivatives containing four contiguous chiral stereocenters was achieved through 1,3-dipolar cycloaddition of isoquinolinium N-ylides in a one-pot three-component reaction. The desired products were obtained in short reaction times and in moderate to high yields (up to 92%) under relatively mild reaction conditions. The structure and relative stereochemistry of the desired product was confirmed by X-ray diffraction analysis.

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4

Sonawane, Amol D., Atsushi Shimozuma, Taro Udagawa, Masayuki Ninomiya, and Mamoru Koketsu. "Synthesis and photophysical properties of selenopheno[2,3-b]quinoxaline and selenopheno[2,3-b]pyrazine heteroacenes." Organic & Biomolecular Chemistry 18, no. 21 (2020): 4063–70. http://dx.doi.org/10.1039/d0ob00718h.

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Novel synthesis of 2-arylselenopheno[2,3-b]quinoxaline, 3-(aryl/alkylselanyl)-2-arylselenopheno[2,3-b]quinoxaline and 6-phenyl-7-(arylselanyl)selenopheno[2,3-b]pyrazine derivatives, from the corresponding 2,3-dichloroquinoxaline and 2,3-dichloropyrazine derivatives.

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5

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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6

Mallisetty, Naga Mohan, Hanumantharao Ganipisetti, Debendra Majhi, and Venkata Nagendra Kumar Putta. "Design, Synthesis of Some New Scaffolds based on Pyrrolyl-Pyridines as Potential Anticancer Agents." Asian Journal of Chemistry 35, no. 2 (2023): 468–74. http://dx.doi.org/10.14233/ajchem.2023.23974.

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Pyrrolyl-pyridine heterocyclic compounds have received considerable attention because of its unique bioisosteric properties and an unusually wide spectrum of biological activities. Thus, it is a perfect framework for the synthesis of novel C–N, C–C bond formations like 5-substituted-1-benzyl-1Hpyrrolo[ 2,3-b]pyridines (3), 2-(1H-pyrrolo[2,3-b]pyridin-5-yl)phenol (5) and screened for their anticancer activity. The synthesized compounds were characterized by 1H NMR, 13C NMR, IR, mass spectral techniques and elemental analysis. The outcomes of these compounds 2,6-difluorobenzylpyrrolidin- 1H-pyrr

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7

Goszczycki, Piotr, Katarzyna M. Stadnicka, Mateusz Z. Brela, and Katarzyna Ostrowska. "The origin of conformational solvatochromism in phenylmethylidene-bis(pyrrolo[2,3-b]quinoxaline) derivative." Dyes and Pigments 193 (September 2021): 109475. http://dx.doi.org/10.1016/j.dyepig.2021.109475.

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8

Keivanloo, Ali, Mohammad Bakherad, and Amin Rahimi. "Synthesis of Unexpected Pyrrolo[2,3-b]quinoxaline-2-carbaldehydes via Sonogashira Coupling Reaction." Synthesis 2010, no. 10 (2010): 1599–602. http://dx.doi.org/10.1055/s-0029-1218715.

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9

Guo, Na, Haiyong Jia, Xing You, Du Jiang, Kui Lu, and Peng Yu. "Preparation of Novel Pyrrolo[2,3‐b]pyridine Derivatives via a New Concise Synthetic Approach." Bulletin of the Korean Chemical Society 36, no. 4 (2015): 1143–47. http://dx.doi.org/10.1002/bkcs.10212.

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The pyrrolo[2,3‐b]pyridine core structure, a bioisostere of quinolones, is found in several molecules that possess important biological activity. We describe here a new, concise, three‐step synthesis of pyrrolo[2,3‐b]pyridines starting from L‐alanine. A series of 4,7‐dihydro‐4‐oxo‐1H‐pyrrolo[2,3‐b]pyridine‐5‐carboxylic acid derivatives, which have not been previously reported, were synthesized using this approach.

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10

Vadlakonda, Rajashekar, Sreenivas Enaganti, and Raghunandan Nerella. "INSILICO DISCOVERY OF HUMAN AURORA B KINASE INHIBITORS BY MOLECULAR DOCKING, PHARMACOPHORE VALIDATION AND ADMET STUDIES." Asian Journal of Pharmaceutical and Clinical Research 10, no. 2 (2017): 165. http://dx.doi.org/10.22159/ajpcr.2017.v10i2.14974.

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Objectives: To predict the anticancer potentiality of some newly designed azaindole derivatives gainst human Aurora B kinase and to identify the critical features important for their activity.Methods: Initially, the derivatives of azaindoles, (Z)-2-(oxo-1 H-pyrrolo [2,3-b] pyridine-3 (2H)-ylidene)-N-(p-substituted) hydrazine carbothioamide (scaffold A), (E)-3-((E)-substituted benzylidene hydrazono)-1H-pyrrolo[2,3-b]pyridine-2(3H)-one (scaffold B), and 1-(2-substituted acetyl)-1H- pyrrolo [2,3-b]pyridine-2,3-dione are synthesized and sketched using ACD/ChemSketch (12.0). With the 3D converted c

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11

Wang, Xinye, Yuan Wu, Chuan Ming Wu, et al. "Dibenzo[f,h]furo[2,3-b]quinoxaline-based molecular scaffolds as deep blue fluorescence materials for organic light-emitting diodes." New Journal of Chemistry 46, no. 1 (2022): 419–25. http://dx.doi.org/10.1039/d1nj04934h.

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A novel molecular scaffold, dibenzo[f,h]furo[2,3-b]quinoxaline (3,6-bis(4-isopropylphenyls)-11-phenyldibenzo[f,h]furo[2,3-b]quinoxaline (dP-diBFQ) and furo[2′,3′:5,6]pyrazino[2,3-f][1,10]phenanthroline, were designed, for pure and deep blue emission. OLEDs based on dP-diBFQ shows pure blue emission with CIE coordinates of (0.154, 0.102) and an EQE of 2.28%.

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12

Ramli, Youssef, Hafid Zouihri, Mohamed Azougagh, Ahmed Moussaif, and El Mokhtar Essassi. "2-Phenylthieno[2,3-b]quinoxaline." Acta Crystallographica Section E Structure Reports Online 68, no. 2 (2012): o396. http://dx.doi.org/10.1107/s1600536812000098.

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13

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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14

Wang, Gang, Jie Li, Yixiang Li, et al. "A new type of solid-state luminescent 2-phenylbenzo[g]furo[2,3-b]quinoxaline derivative: synthesis, photophysical characterization and transporting properties." Journal of Materials Chemistry C 7, no. 31 (2019): 9690–97. http://dx.doi.org/10.1039/c9tc02539a.

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We developed a new synthesis method of furo [2,3-b] quinoxaline core and report a new type of 2-phenylbenzo[g]furo [2,3-b] quinoxaline organic semiconductors, which shows 22.1% PLQY in solid powders and hole mobility of 2.58 × 10<sup>−2</sup> cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>.

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15

Keivanloo, Ali, Mohammad Bakherad, and Amin Rahimi. "ChemInform Abstract: Synthesis of Unexpected Pyrrolo[2,3-b]quinoxaline-2-carbaldehydes via Sonogashira Coupling Reaction." ChemInform 41, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.201037162.

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16

M.H. Hilmy, Khaled, Fawzya N.M. Kishk, Esmat B.A. Shahen, and Mohamed A. Hawata. "Novel pyrrolo[2,3-b]pyridine and pyrrolo[2,3-d] pyrimidine derivatives: Design, synthesis, and structure elucidation." Bulletin of the Chemical Society of Ethiopia 37, no. 4 (2023): 983–92. http://dx.doi.org/10.4314/bcse.v37i4.14.

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ABSTRACT. A cyclo condensation reaction is an effective method for a two-component reaction of 2-amino-1,5-diphenyl-1H-pyrrole-3-carbonitrile 3a-c and active methylene compounds in acetic acid and catalytic hydrochloric acid to produce new substituted 1H-pyrrolo[2,3-b]pyridine 4a-c, 5a-c, and 6a-c have been established. Additionally, a new series of substituted 1H-pyrrolo[2,3-d]pyrimidines 7a-c and 8a-c could be synthesized utilizing a feasible and efficient approach, including urea and thiourea substrates. Spectroscopic data IR, MS, 1H, and 13C NMR, as well as elemental analyses, elucidated t

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17

Anothane, Caleb Ahoya, and El Mokhtar Essassi. "2-(3-thienyl)-2,3-dihydrofuro[2,3-b]quinoxaline." Molbank 2007, no. 2 (2007): M536. http://dx.doi.org/10.3390/m536.

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18

Lassagne, Frédéric, Timothy Langlais, Elsa Caytan, et al. "From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines." Molecules 23, no. 11 (2018): 2961. http://dx.doi.org/10.3390/molecules23112961.

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2,3-Diphenylated quinoxaline, pyrido[2,3-b]pyrazine and 8-bromopyrido[3,4-b]pyrazine were halogenated in deprotometalation-trapping reactions using mixed 2,2,6,6-tetramethyl piperidino-based lithium-zinc combinations in tetrahydrofuran. The 2,3-diphenylated 5-iodo- quinoxaline, 8-iodopyrido[2,3-b]pyrazine and 8-bromo-7-iodopyrido[3,4-b]pyrazine thus obtained were subjected to palladium-catalyzed couplings with arylboronic acids or anilines, and possible subsequent cyclizations to afford the corresponding pyrazino[2,3-a]carbazole, pyrazino[2′,3′:5,6] pyrido[4,3-b]indole and pyrazino[2′,3′:4,5]p

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19

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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20

Hung, Tran Quang, Do Huy Hoang, Ngo Ngoc Thang, et al. "Palladium catalyzed synthesis and physical properties of indolo[2,3-b]quinoxalines." Org. Biomol. Chem. 12, no. 32 (2014): 6151–66. http://dx.doi.org/10.1039/c4ob00841c.

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21

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, form

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22

Medhat, A. Zabran. "Some reactions with quinoxaline-2,3-dicarboxylic acid anhydride. Synthesis of quinazolinoquinoxalines and quinazolino[2,3:6,1]pyridazino[4,5-b]quinoxalines." Journal of Indian Chemical Society Vol. 77, Oct 2000 (2000): 494–96. https://doi.org/10.5281/zenodo.5867944.

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Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, P. Box. 11884, Cairo, Egypt <em>Manuscript received 17 August 1998, revised 27 June 2000, accepted 28 July 2000</em> Many derivatives of quinazolinoquinoxalines and quinazolino[2,3:6,1]pyridazino[4,5-<em>b</em>]quinoxaline have been prepared starting from quinoxaline-2,3-dicarboxylic acid anhydride.

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23

Nguyen, Nguyen Tran, Vo Viet Dai, Adam Mechler, Luc Van Meervelt, Nguyen Thi Hoa, and Quan V. Vo. "Synthesis and computational evaluation of the antioxidant activity of pyrrolo[2,3-b]quinoxaline derivatives." RSC Advances 14, no. 34 (2024): 24438–46. http://dx.doi.org/10.1039/d4ra03108c.

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24

Y., A. AMMAR, M. ISMAIL I., M. SH. EL-SHARIEF A., A. MOHAMED Y., and M. AMER R. "Synthesis of some Newer Thiazolo and Thiadiazino Derivatives from 6-Methyl- or 6-Nitro-2,3-dichloroquinoxalines." Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 124–27. https://doi.org/10.5281/zenodo.6303632.

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Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt <em>Manuscript received 23 October 1987, revised 18 August 1988, accepted 18 November 1988</em> lnteraction or 6-methyl or 6-nitro-2,3-dichloroquinoxaline (1a, b) with thiourea in ethanol led to the formation or diquinoxalino[2,3-<em>b</em>: 2',3'-<em>e</em>]-1,4-dithiien derivatives (2a, b) with 2-imino-2,3-dihydrothiazolol [4,5-<em>b</em> ]quinoxalines (3a, b). 7-Methyl- or 7- nitro-3-amino-2-imino-2,3-dihydrothiazolo[4,5-<em>b</em>]quinoxaline (6a, b) were prepared and reacted with acid

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25

Sumby, Christopher J. "Ruthenium(II) Complexes of New Chelating Indolizino[2,3-b]pyrazine- and Indolizino[2,3-b]quinoxaline-Derived Ligands: Syntheses, Electrochemistry and Absorption Spectroscopy." Australian Journal of Chemistry 61, no. 11 (2008): 894. http://dx.doi.org/10.1071/ch08339.

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The highly conjugated chelating ligands 5-(2-pyridyl)indolizino[2,3-b]pyrazine 1, 5-(2-pyridyl)indolizino[2,3-b]quinoxaline 2, and 8,9-dimethyl-5-(2-pyridyl)indolizino[2,3-b]quinoxaline 3 were prepared in one step, with good yields, from di-2-pyridylmethane and 2,3-dichloropyrazine, 2,3-dichloroquinoxaline, and 8,9-dimethyl-2,3-dichloroquinoxaline, respectively. Compounds 1–3 display long-wavelength absorption maxima in the green (1) and yellow (2 and 3) to give intensely coloured red and purple solutions, respectively. Bis(2,2′-bipyridyl)ruthenium(ii) and bis(4,4′-dimethyl-2,2′-bipyridyl)ruth

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26

Evers, David L., Julie M. Breitenbach, Katherine Z. Borysko, Leroy B. Townsend, and John C. Drach. "Inhibition of Cyclin-Dependent Kinase 1 by Purines and Pyrrolo[2,3-d]Pyrimidines Does Not Correlate with Antiviral Activity." Antimicrobial Agents and Chemotherapy 46, no. 8 (2002): 2470–76. http://dx.doi.org/10.1128/aac.46.8.2470-2476.2002.

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ABSTRACT We have previously shown that a series of nonnucleoside pyrrolo[2,3-d]pyrimidines selectively inhibit the replication of herpes simplex virus type 1 (HSV-1) and human cytomegalovirus (HCMV). These compounds act at the immediate-early or early stage of HCMV replication and have antiviral properties somewhat similar to those of roscovitine and olomoucine, specific inhibitors of cyclin-dependent kinases (cdks). In the present study we examine the hypothesis that pyrrolo[2,3-d]pyrimidines exert their antiviral effects by inhibition of cellular cdks. Much higher concentrations of a panel o

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27

Iaroshenko, Viktor, Yan Wang, Dmitri Sevenard, and Dmitriy Volochnyuk. "Synthesis of Fluorinated Pyrrolo[2,3-b]pyridine and Pyrrolo[2,3-d]pyrimidine Nucleosides." Synthesis 2009, no. 11 (2009): 1851–57. http://dx.doi.org/10.1055/s-0029-1216640.

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28

Besharati-Seidani, Tayebeh, Ali Keivanloo, Babak Kaboudin, and Tsutomu Yokomatsu. "Efficient synthesis of 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxalines via Sonogashira coupling reaction followed by iodocyclization and subsequent palladium-catalyzed cross-coupling reactions." RSC Advances 6, no. 87 (2016): 83901–8. http://dx.doi.org/10.1039/c6ra15425e.

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In this paper, we report the successful synthesis of new 2-phenyl-3-substituted furo/thieno[2,3-b]quinoxaline derivatives from 2-chloro-3-methoxyquinoxaline and 2-chloro-3-(methylthio)quinoxaline by a three-step approach.

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29

Gala, Elena, Marta Cordoba, M. Luisa Izquierdo, and Julio Alvarez-Builla. "Gold catalysis in the synthesis of azaindoles: pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrazines." Arkivoc 2014, no. 5 (2014): 319–40. http://dx.doi.org/10.3998/ark.5550190.p008.720.

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30

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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31

Ghotekar, Bhausaheb K., Muddassar A. Kazi, Madhukar N. Jachak, and Raghunath B. Toche. "Effect of substituents on absorption and fluorescence properties of pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines." Canadian Journal of Chemistry 86, no. 11 (2008): 1070–76. http://dx.doi.org/10.1139/v08-155.

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A convenient route was successfully developed for the synthesis of novel heterocycles such as pyrazolo[3,4-b]pyrrolo[2,3-d]pyridines (PPP) from pyrazolo[3,4-b]pyridines in good yield. The PPP derivatives synthesized were further studied for their photophysical properties, and it was observed that absorption and emission λmax changed, owing to the substituent effect at 4 positions. These compounds were obtained from highly reactive starting materials, 5-aminopyrazoles and α-acetyl γ-butyrolactone.Key words: α-acetyl γ-butyrolactone, pyrazolo[3,4-b]pyrrolo[2,3-d] pyridine, absorption, emission,

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32

Karpov, Sergey, Arthur Grigor’ev, Yakov Kayukov, Iuliia Gracheva, and Victor Tafeenko. "Cascade Regioselective Heterocyclization of 2-Acyl-1,1,3,3-tetracyanopropenides: Synthesis of Pyrrolo[3,4-c]pyridine and Pyrrolo[3,4-d]thieno[2,3-b]pyridine Derivatives." Synlett 28, no. 13 (2017): 1592–95. http://dx.doi.org/10.1055/s-0036-1588823.

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2-Acyl-1,1,3,3-tetracyanopropenides (ATCN) undergo cascade heterocyclization under the action of aliphatic thiols, resulting in the formation of 6-(alkylthio)-4-amino-1-aryl(alkyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles. The involvement of methyl mercaptoacetate to this reaction leads to the formation of the methyl 4,8-diamino-1-aryl-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-d]thieno[2,3-b]pyridine-7-carboxylates, containing a new fused heterocyclic scaffold.

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33

Rasmussen, Seth, Trent Anderson, Evan Culver, Furqan Almyahi, and Paul Dastoor. "Poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline): Processible, Low-Bandgap, Ambipolar-Acceptor Frameworks via Direct Arylation Polymerization." Synlett 29, no. 19 (2018): 2542–46. http://dx.doi.org/10.1055/s-0037-1610299.

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The synthesis of a new dialkyl-functionalized quinoxaline acceptor, 5,8-dibromo-2,3-dihexylquinoxaline, is reported, along with its cross-coupling with 2,3-dihexylthieno[3,4-b]pyrazine via direct arylation polymerization. The resulting ambipolar-acceptor polymer poly(2,3-dihexylthieno[3,4-b]pyrazine-alt-2,3-dihexylquinoxaline) exhibits a low bandgap of 1.07 eV and high solubility. The results of initial organic photovoltaic devices are also reported.

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34

Loloiu, G., T. Loloiu, and O. Maior. "Synthesis of 1H-pyrrolo[2,3-b]phenoxathiin-2,3-dione." Chemistry of Heterocyclic Compounds 34, no. 3 (1998): 363–66. http://dx.doi.org/10.1007/bf02290733.

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35

Glushkov, R. G., L. N. Dronova, A. S. Elina, et al. "Synthesis of pyrido[2,3-b]quinoxaline derivatives." Pharmaceutical Chemistry Journal 22, no. 3 (1988): 242–49. http://dx.doi.org/10.1007/bf00758278.

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36

Han, Jianxin, Sheng-Tong Niu, Yushuang Liu, et al. "Robustanoids A and B, two novel pyrrolo[2,3-b]indole alkaloids from Coffea canephora: isolation and total synthesis." Organic Chemistry Frontiers 5, no. 4 (2018): 586–89. http://dx.doi.org/10.1039/c7qo00931c.

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37

Okamoto, Yoshinari, Yumiko Kaneda, Tetsuo Yamasaki, Tadashi Okawara, and Mitsuru Furukawa. "Simple preparation of fused pyrrolo[2,3-b]pyrrolidinones and pyrrolo[2,3-c]pyridazinones 1." Journal of the Chemical Society, Perkin Transactions 1, no. 9 (1997): 1323–28. http://dx.doi.org/10.1039/a607816h.

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38

Lyadov, Vadim A., Dmitry E. Makrushin, Ekaterina S. Denislamova, Andrey N. Maslivets, Galina A. Triandafilova, and Sergei I. Solodnikov. "SYNTHESIS AND ANALGESIC ACTIVITY OF METHYL-1-ANTIPYRYL-4-AROYL-2,3-DIOXO-2,3,5,10-TETRAHYDROBENZO[B]PYRROLO[2,3-E][1,4]DIAZEPINE-10A(1H) –CARBOXYLATES." ChemChemTech 67, no. 5 (2024): 17–23. http://dx.doi.org/10.6060/ivkkt.20246705.6939.

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In order to obtain new biologically active compounds, methyl-1-antipyryl-4-aroyl-2,3-dioxo-2,3,5,10-tetrahydrobenzo[b]pyrrolo[2,3-e][1,4]diazepine was synthesized-10a(1H)-carboxylates by reacting 1-antipyryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with o-phenylenediamine. The structures of the obtained compounds were confirmed by 1H NMR, IR spectroscopy, X-ray diffraction and elemental analysis. The presence of several electrophilic centers in the structure of antipyryl-substituted 1H-pyrrole-2,3-diones gives them a high reactivity with respect to binucleophilic reagents. Apparently, t

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39

Armand, Joseph, Line Boulares, Christian Bellec, and Jean Pinson. "Chemical and electrochemical reduction of pyrazino[2,3-g]quinoxalines and of their benzo and dibenzo derivatives; the structure of fluorindine and the formation of tetraanion." Canadian Journal of Chemistry 65, no. 7 (1987): 1619–23. http://dx.doi.org/10.1139/v87-271.

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The structure of fluorindine is established by nmr as the 5,14-dihydroquinoxalino[2,3-b]phenazine. The catalytic hydrogenation of 2,3-di(p-methoxyphenyl)pyrazino[2,3-b]phenazine 2a leads to the 6,11-dihydro derivative 4a. The electrochemical reduction in an hydroorganic medium furnishes 4a and then the 1,4,6,11-tetrahydro derivative 8a. In dry DMSO the voltammogram shows four monoelectronic reversible systems corresponding to the successive formation of a radical anion, dianion, radical trianion, and tetraanion. Thus 2a appears as a new example of the very restricted class of compounds leading

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40

Bathula, Chandramohan, Catarina Roma-Rodrigues, Jyoti Chauhan, Alexandra R. Fernandes та Subhabrata Sen. "Synthesis of tetrahydro-1H-indolo[2,3-b]pyrrolo[3,2-c]quinolones via intramolecular oxidative ring rearrangement of tetrahydro-β-carbolines and their biological evaluation". New Journal of Chemistry 42, № 8 (2018): 6538–47. http://dx.doi.org/10.1039/c7nj04616b.

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41

Rao, Mandava V. B., Dandamudi SriLaxmi, Suryadevara V. Vardhini, Venkata R. Guttikonda, Ravikumar Kapavarapu, and Manojit Pal. "Sonochemical Synthesis of 6‐Substituted Indolo[3′,2′:4,5]pyrrolo[2,3‐ b ]quinoxaline Derivatives as Potential Cytotoxic Agents." ChemistrySelect 5, no. 45 (2020): 14239–46. http://dx.doi.org/10.1002/slct.202002951.

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42

Štarha, Pavel, and Zdeněk Trávníček. "5-Bromo-1H-pyrrolo[2,3-b]pyridine." Acta Crystallographica Section E Structure Reports Online 69, no. 3 (2013): o381. http://dx.doi.org/10.1107/s1600536813004157.

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43

Minakata, Satoshi, Shinobu Itoh, Mitsuo Komatsu, and Yoshiki Ohshiro. "Functionalization of 1H-Pyrrolo[2,3-b]pyridine." Bulletin of the Chemical Society of Japan 65, no. 11 (1992): 2992–97. http://dx.doi.org/10.1246/bcsj.65.2992.

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44

Pratima Nikalje, Anna, France-Aimée Alphonse, Sylvain Routier, Gérard Coudert, and Jean-Yves Mérour. "A Straightforward Synthesis of Pyridopyrazino[2,3-b]indoles and Indolo[2,3-b]quinoxaline." HETEROCYCLES 55, no. 5 (2001): 925. http://dx.doi.org/10.3987/com-01-9181.

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45

Hordiyenko, Olga, Igor Rudenko, Irina Zamkova, et al. "Facile Synthesis of Hydrazine Derivatives of 5H-Pyrrolo[3,4-b]pyrazine and 1H-Pyrrolo[3,4-b]quinoxaline." Synthesis 45, no. 24 (2013): 3375–82. http://dx.doi.org/10.1055/s-0033-1340042.

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46

Arcadi, Antonio, Sandro Cacchi, Giancarlo Fabrizi, and Luca M. Parisi. "2,3-Disubstituted pyrrolo[2,3-b]quinoxalines via aminopalladation–reductive elimination." Tetrahedron Letters 45, no. 11 (2004): 2431–34. http://dx.doi.org/10.1016/j.tetlet.2004.01.058.

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47

Nikumbh, Satish P., Akula Raghunadh, T. Srinivasa Rao, et al. "A cascade reaction for the new and direct synthesis of indolofuroquinoxalines." RSC Advances 6, no. 28 (2016): 23489–97. http://dx.doi.org/10.1039/c6ra03556f.

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48

Chen, Xiu-Yu, Ying Han, Jing Sun, and Chao-Guo Yan. "Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction." Beilstein Journal of Organic Chemistry 20 (June 28, 2024): 1436–43. http://dx.doi.org/10.3762/bjoc.20.126.

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An efficient protocol for the synthesis of polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates was developed by a three-component reaction. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates and 5,6-unsubstituted 1,4-dihydropyridines in refluxing acetonitrile afforded polyfunctionalized tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine-3,4b,5,6,7(1H)-pentacarboxylates in high yields and with high diastereoselectivity. The reaction was finished by in situ generation of activated 5-(alkylimino)

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49

Yang, Zhao-Ying, Tian Tian, Ya-Fei Du, et al. "Direct intramolecular amination of tryptophan esters to prepare pyrrolo[2,3-b]indoles." Chemical Communications 53, no. 57 (2017): 8050–53. http://dx.doi.org/10.1039/c7cc03983b.

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50

Lystsova, Ekaterina A., Anastasia D. Novokshonova, Pavel V. Khramtsov, et al. "Reaction of Pyrrolobenzothiazines with Schiff Bases and Carbodiimides: Approach to Angular 6/5/5/5-Tetracyclic Spiroheterocycles." Molecules 29, no. 9 (2024): 2089. http://dx.doi.org/10.3390/molecules29092089.

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1H-Pyrrole-2,3-diones, fused at [e]-side with a heterocycle, are suitable platforms for the synthesis of various angular polycyclic alkaloid-like spiroheterocycles. Recently discovered sulfur-containing [e]-fused 1H-pyrrole-2,3-diones (aroylpyrrolobenzothiazinetriones) tend to exhibit unusual reactivity. Based on these peculiar representatives of [e]-fused 1H-pyrrole-2,3-diones, we have developed an approach to an unprecedented 6/5/5/5-tetracyclic alkaloid-like spiroheterocyclic system of benzo[d]pyrrolo[3′,4′:2,3]pyrrolo[2,1-b]thiazole via their reaction with Schiff bases and carbodiimides. T

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