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Journal articles on the topic '3-b] quinolines'

Author: Grafiati

Published: 4 June 2025

Last updated: 1 August 2025

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1

Sonawane, Amol D., Dinesh R. Garud, Taro Udagawa, and Mamoru Koketsu. "Synthesis of thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivativesviaiodocyclization reaction and a DFT mechanistic study." Organic & Biomolecular Chemistry 16, no. 2 (2018): 245–55. http://dx.doi.org/10.1039/c7ob02523h.

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Thieno[2,3-b]quinoline and selenopheno[2,3-b]quinoline derivatives were synthesized by the regioselective iodocyclization reaction of 3-alkynyl-2-(methylthio)quinolines and 3-alkynyl-2-(methylseleno)quinolines.

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2

Xie, Jian-Wu, Jia-Wen Zhang, Li-Si-Han Yu, Jian-Lian Dong, and Qi-Chao Sun. "Enantioselective Construction and Transformations of Polyfunctionalized 3,4-Dihydro-2H-thiopyrano[2,3-b]quinolines." Synlett 29, no. 05 (2017): 603–8. http://dx.doi.org/10.1055/s-0036-1591838.

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We developed an enantioselective organocascade Michael/Henry reaction in the presence of a bifunctional organocatalyst to construct chiral polyfunctionalized 3,4-dihydro-2H-thiopyrano[2,3-b]quinolines. The resulting optically active products with three contiguous stereocenters, one quaternary and two tertiary, were obtained in moderate to good yields and with good to excellent enantioselectivities. Remarkably, the resulting products were readily converted into polyfunctionalized optically active furo[2′,3′:4,5]thiopyrano[2,3-b]quinoline, 3,4-dihydro-2H-thiopyrano[2,3-b]quinoline 1-oxide and 2,

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3

Portilla, Jaime, Jairo Quiroga, Manuel Nogueras, et al. "Structural comparisons of isomeric series of 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines and 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines." Acta Crystallographica Section B Structural Science 64, no. 1 (2008): 72–83. http://dx.doi.org/10.1107/s0108768107065743.

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The structures of three new 7-aryl-benzo[h]pyrazolo[3,4-b]quinolines, 8-methyl-7-(4-chlorophenyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, C27H20ClN3, 8-methyl-7-(3-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[b]pyrazolo[3,4-b]quinoline, C26H20N4, and 8-methyl-7-(4-pyridinyl)-10-phenyl-10H-benzo[h]pyrazolo[3,4-b]quinoline, C26H18N4, which is an unexpected oxidation product isolated from the attempted synthesis of 8-methyl-7-(4-pyridinyl)-10-phenyl-6,10-dihydro-5H-benzo[h]pyrazolo[3,4-b]quinoline, and those of three new 11-aryl-benzo[f]pyrazolo[3,4-b]quinolines, 11-(4-methylphe

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4

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 945. http://dx.doi.org/10.1071/ch19363.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implicatio

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5

Abd El-Aal, Hassan A. K., and Talaat I. El-Emary. "Corrigendum to: Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence." Australian Journal of Chemistry 72, no. 12 (2019): 990. http://dx.doi.org/10.1071/ch19363_co.

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An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implicatio

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6

Wang, Cunde, Xushun Qing, Ting Wang, Chenlu Dai, and Zhenjie Su. "Direct Synthesis of 6H-Chromeno[3,4-b]quinolin-6-ol Derivatives from Substituted 3-Nitro-2H-chromenes and 2-Nitrobenzaldehydes Mediated by Fe/AcOH System." Synthesis 50, no. 06 (2017): 1350–58. http://dx.doi.org/10.1055/s-0036-1589154.

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An efficient iron/acetic acid system-mediated reductive cyclization reaction of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes for the synthesis of 6-aryl-6H-chromeno[3,4-b]quinolines was developed. This reaction involves the sequential reduction, hydrolysis, aldol condensation, intramolecular addition, and the nucleophilic addition of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes to give the corresponding 6H-chromeno[3,4-b]quinolines. This transformation provides a straightforward synthetic protocol for constructing substituted 6H

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7

Bakhite, Etify Abdel-Ghafar. "Synthesis and Reactions of Some New 3-Amino-2-substituted Thieno[2,3-b]quinolines." Collection of Czechoslovak Chemical Communications 57, no. 11 (1992): 2359–66. http://dx.doi.org/10.1135/cccc19922359.

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Reaction of 3-cyano-quinolin-2(1H)-thione (II) with ω-bromoacetophenones gave 3-amino-2-aroyl-thieno[2,3-b]quinolines (IVa-IVd). Whereas, interaction of II with chloroacetanilides yielded the corresponding thioesters Va-Vc which cyclized into 3-amino-2-arylcarbamoylthiene[2,3-b]quinolines (VIa-VIc) on treatment with ethoxide. Compounds VIa-VIc were reacted with nitrous acid, triethyl orthoformate and carbon disulfide to afford the fused polycyclic compounds VIIa-VIIc, VIIIa-VIIIc and IXa-IXc, respectively. Also treatment of IXa-IXc with ethyl iodide gave 3-ethylthio derivatives Xa-Xc. Moreover

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8

Shiri, Morteza, Maryam-Sadat Tonekaboni, Zahra Tanbakouchian, and Soma Majedi. "Synthesis of [1,4]Oxathiepino[5,6-b]quinolines via Base-Mediated Intramolecular Hydroalkoxylation." SynOpen 06, no. 01 (2022): 7–10. http://dx.doi.org/10.1055/s-0040-1719868.

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AbstractA base-mediated intramolecular hydroalkoxylation that was used to prepare a series of seven-membered S,O-heterocycles is described. 2-Thiopropargyl-3-hydroxymethyl quinolines were prepared starting from 2-mercaptoquinoline-3-carbaldehydes, via S-propargylation and reduction of a formyl group. Interestingly, 2-mercaptopropargyl-3-hydroxymethyl quinolines were converted into the corresponding oxathiepinoquinolines in the presence of t-BuOK. It is proposed that the S-propargyl moiety, in the presence of base, is converted into its allenyl isomer; subsequent addition of a hydroxyl group to

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9

Morteza, Shiri, Fathollahi-Lahroud Mina, and Yasaei Zahra. "A novel strategy for the synthesis of 6H-chromeno [4, 3-b] quinoline by intramolecular Heck cyclization." Tetrahedron 73, no. 17 (2017): 2501–3. https://doi.org/10.1016/j.tet.2017.03.043.

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A novel procedure for the synthesis of various derivatives of 6H-chromeno [4, 3-b] quinolines from intramolecular Heck reaction of 2-chloro-3-(phenoxymethyl) quinolines is described in this study. Intramolecular cyclization of N-alkylated indoles was efficiently investigated as well. The reaction is catalyzed by bis (triphenylphosphine) palladium (II) dichloride in acetonitrile at 80 °C.

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10

Wojciechowski, Krzysztof, and Michał Nowacki. "Synthesis of [1]Benzothieno[2,3-b]quinolines via Transition-Metal-Free [3+3] Annulation of Nitroarenes and Benzo[b]thiophen-3-ylacetonitrile or 3-(Phenylsulfonylmethyl)benzo[b]thiophene Carbanions." Synthesis 49, no. 16 (2017): 3794–800. http://dx.doi.org/10.1055/s-0036-1588426.

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Benzo[b]thiophen-3-ylacetonitriles or 3-(phenylsulfonylmethyl)benzo[b]thiophenes react with nitrobenzene derivatives in the presence of potassium tert-butoxide and chlorotrimethylsilane to form, in good yields, 11-cyano- or 11-(phenylsulfonyl)[1]benzothieno[2,3-b]quinolines, respectively.

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11

Abramov, Michael A., Suzanne Toppet, and Wim Dehaen. "Regiospecific Nucleophilic Substitution of Fluorine in Fused Tetrafluoroquinolines with N- and O-Nucleophiles." Journal of Chemical Research 2002, no. 8 (2002): 357–58. http://dx.doi.org/10.3184/030823402103172455.

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5,6,7,8-Tetrafluoro-1,2-azolo[3,4- b;4′,3′- e]quinolines react regiospecifically with aliphatic and aromatic amines, alcohols and phenols yielding 7-substituted 5,6,8-trifluoro-1,2-azolo[3,4- b;4′,3′- e]quinolines.

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12

Morteza, Shiri, Hamidi Hoda, A. Oskooie Hossein, et al. "Synthesis and anti-bacterial evaluation of novel thio- and oxazepino[7,6-b]quinolines." Journal of the Iranian Chemical Society 12, no. 12 (2015): 2205–12. https://doi.org/10.1007/s13738-015-0698-5.

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Cyclocondensation of 2-chloroquinoline-3-carbaldehydes and 2-thiophenol/2aminophenols led to the formation of benzo[2,3][1,4]thio- or oxazepino[7,6-b]quinolines. Ugi reaction of the latter compound with various carboxylic acids and isocyanides gave novel oxazepino[7,6b]quinoline derivatives. All compounds were evaluated for their antibacterial and anti-fungal activities. Among them, compounds 4a, 4b and 4d showed moderate to good activity.

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13

Kumar, Alleni Suman, Rathod Aravind Kumar, Vavilapally Satyanarayana, et al. "Catalyst-Free Synthesis of Novel 6-Phenyl-6H-chromeno [4, 3-b] quinoline Derivatives at RT: Their Further Structure Evaluation Leads to Potential Anti-cancer Agents." Natural Product Communications 12, no. 7 (2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200732.

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A variety of novel quinoline derivatives (6-phenyl-6 H-chromeno [4,3- b] quinoline) have been prepared by using 4-chloro-2-phenyl-2 H-chromene-3-carbaldehyde and various substituted of aromatic anilines as starting materials. This is the first example on the preparation of quinolines through this novel method. And the resulting quinoline derivatives further structure evolution is leads to an anti cancer agents. Our preliminary data of model compound (7i) on three cancer cell lines (B16F10, MCF7 and A549) suggested decent anticancer activity on two cell lines (B16F10 and MCF7) with IC50 values

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14

Amirnejat, Sara, Aliakbar Nosrati, and Shahrzad Javanshir. "Synthesis of Functionalized Thiopyrano [2,3-b]quinolines via Cascade Reactions Catalyzed by Magnetic Arginine/Alginate Biocomposite." Chemistry Proceedings 3, no. 1 (2020): 129. http://dx.doi.org/10.3390/ecsoc-24-08413.

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An effective synthesis of functionalized thiopyrano [2,3-b]quinolines has been described via cascade reactions using super paramagnetic iron oxide nanoparticles (SPIONs) coated with l-arginine (Arg) grafted alginate (Alg), called Fe3O4@Alg@CPTMS@Arg. The reaction was performed between commercially available CH acid compounds such as dimedone or malononitrile, and 2-mercapto-quinoline-3-carbaldehydes under green conditions. This efficient method provides a new route for the formation of functionalized three or four fused rings.

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15

Ghorab, Mostafa M., Mansour S. Alsaid, Mohammed S. Al-Dosari, Fatma A. Ragab, Abdullah A. Al-Mishari, and Abdulaziz N. Almoqbil. "Novel quinolines carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole and thiophene moieties as potential anticancer agents." Acta Pharmaceutica 66, no. 2 (2016): 155–71. http://dx.doi.org/10.1515/acph-2016-0016.

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Abstract As a part of ongoing studies in developing new anticancer agents, novel 1,2-dihydropyridine 4, thienopyridine 5, isoquinolines 6–20, acrylamide 21, thiazolidine 22, thiazoles 23–29 and thiophenes 33–35 bearing a biologically active quinoline nucleus were synthesized. The structure of newly synthesized compounds was confirmed on the basis of elemental analyses and spectral data. All the newly synthesized compounds were evaluated for their cytotoxic activity against the breast cancer cell line MCF7. 2,3-Dihydrothiazole-5-carboxamides 27, 25, 4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxa

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16

Rajamanickam, P., and P. Shanmugam. "Synthesis of 4-Cyanofuro(2,3-b)quinolines." Zeitschrift für Naturforschung B 48, no. 4 (1993): 517–20. http://dx.doi.org/10.1515/znb-1993-0419.

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17

Eid, Elshimaa M., Huwaida M. E. Hassaneen, Ahmed H. M. Elwahy, and Ismail A. Abdelhamid. "Hantzsch-like synthesis of novel bis(hexahydroacridine-1,8-diones), bis(tetrahydrodipyrazolo[3,4-b:4′,3′-e]pyridines), and bis(pyrimido[4,5-b]quinolines) incorporating thieno[2,3-b]thiophenes." Journal of Chemical Research 44, no. 11-12 (2020): 653–59. http://dx.doi.org/10.1177/1747519820917886.

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A novel series of bis(hexahydroacridine-1,8-diones), bis(tetrahydrodipyrazolo[3,4- b:4′,3′- e]pyridines), and bis(pyrimido[4,5- b]quinolines) incorporating a thieno[2,3- b]thiophene core via ether or ester linkages is prepared via a Hantzsch-like reaction.

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18

Barker, David, Lisa Pilkington, Natalie Haverkate, Michelle van Rensburg, Johannes Reynisson, and Euphemia Leung. "Synthesis of 3-Amino-2-carboxamide Tetrahydropyrrolo[2,3-b]quinolines." Synlett 27, no. 20 (2016): 2811–14. http://dx.doi.org/10.1055/s-0036-1588619.

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19

Danel, Andrzej, Elżbieta Porębska, Kacper Markiel, et al. "Multicomponent Synthesis of 4-Aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines Using L-Proline as a Catalyst—Does It Really Proceed?" Molecules 28, no. 22 (2023): 7612. http://dx.doi.org/10.3390/molecules28227612.

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Looking for effective synthetic methods for 1H-pyrazolo[3,4-b]quinolines preparation, we came across a procedure where, in a three-component reaction catalysed by L-proline, 4-aryl-4,9-dihydro-1H-pyrazolo[3,4-b]quinolines are formed. These compounds can be easily oxidised to a fully aromatic system, which gives hope for a synthetic method that could replace, e.g., Friedländer condensation, often used for this purpose, even though severely limited by the availability of suitable substrates. However, after careful repetition of the procedures described in the publication, it turned out that the

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20

Ito, Hajime. "Copper-catalyzed asymmetric dearomative borylation: new pathway to optically active heterocyclic compounds." Pure and Applied Chemistry 90, no. 4 (2018): 703–10. http://dx.doi.org/10.1515/pac-2017-0912.

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AbstractChiralN-heterocyclic organoboronates represent promising intermediates for the preparation of various bioactive and pharmaceutical compounds. We recently reported the first asymmetric dearomative borylation of indoles by copper-catalyzed borylation. Then we further developed dearomatization/enantioselective borylation sequence. Chiral 3-boryl-tetrahydropyridines and chiral boryl-tetrahydroquinolines via the copper(I)-catalyzed regio-, diastereo- and enantioselective borylation of 1,2-dihydropyridines and 1,2-dihydroquinilines, which were prepared by the partial reduction of the corresp

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21

Zhu, Chao-Qun, Zhuo-Fei Deng, Yahong Zhang, and You-Qing Wang. "Synthesis of 4-substituted 3-(2-hydroxyphenyl)-quinolines through an unexpected iron(iii) chloride promoted reaction of cyclic imine dibenzo[b,f][1,4]oxazepines with alkynes." Organic Chemistry Frontiers 4, no. 2 (2017): 196–203. http://dx.doi.org/10.1039/c6qo00545d.

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22

Kumar, Sundaravel Vivek, Shanmugam Muthusubramanian, and Subbu Perumal. "Facile “on water” domino reactions for the expedient synthesis of 2H-thiopyrano[2,3-b]quinolines." RSC Advances 5, no. 39 (2015): 30826–32. http://dx.doi.org/10.1039/c5ra04795a.

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A facile synthesis of novel 3-nitro-2-aryl-2H-thiopyrano[2,3-b]quinolines from the domino reactions of 2-mercaptoquinoline-3-carbaldehyde and substituted β-nitrostyrenes in the presence of triethylamine (TEA) in water is described.

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23

Nowacki, Michał, and Krzysztof Wojciechowski. "Simple synthesis 11-substituted norcryptotackieine derivatives." RSC Advances 5, no. 114 (2015): 94296–303. http://dx.doi.org/10.1039/c5ra18626a.

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11-Substituted indolo[2,3-b]quinolines were obtained in reactions ofN-protected indol-3-yl-acetonitrile, -acetate, and -methylsulfone with nitrobenzene derivatives in presence of base and trialkylchlorosilanes.

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24

Lin, Yan-Liang, Yun-Ta Lee, Indrajeet J. Barve, Yi-Ting Huang, and Chung-Ming Sun. "Rapid synthesis of hexahydropyrrolo[3,4-b]pyrrole-fused quinolines via a consecutive [3 + 2] cycloaddition and reduction/intramolecular lactamization cascade." Organic Chemistry Frontiers 7, no. 19 (2020): 2991–96. http://dx.doi.org/10.1039/d0qo00858c.

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An unprecedented synthesis of novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines is achieved through the sequential [3 + 2] cycloaddition reaction of azomethine ylides with maleimides followed by intramolecular lactamization.

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25

Mishra, Kalpana, Jay Bahadur Singh, Tanu Gupta, and Radhey M. Singh. "TBAB-catalyzed cascade reactions: facile synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines via 5-exo-dig cyclization of o-arylalkynylquinoline aldehydes." Organic Chemistry Frontiers 4, no. 10 (2017): 1926–30. http://dx.doi.org/10.1039/c7qo00273d.

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TBAB-catalyzed cascade reaction condition is developed for the synthesis of 1-trifluoromethyl-3-alkylidene-1,3-dihydrofuro[3,4-b]quinolines from o-arylalkynylquinoline aldehydes via 5-exo-dig cyclization.

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26

Xiao, Xiao, Bingxuan Shao, Jingyi Li, et al. "Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-b]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones." Chemical Communications 57, no. 38 (2021): 4690–93. http://dx.doi.org/10.1039/d1cc00989c.

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An enantioselective synthesis of 1,4-dihydropyrazolo[4′,3′:5,6]pyrano[2,3-b]quinolines from modified MBH carbonates and pyrazolones via a chiral phosphine-mediated alkylation/annulation sequence has been realized.

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27

El-Ashmawy, M. B., M. A. El-Sherbeny, and N. S. El-Gohary. "Synthesis and antitumor screening of new series of pyrimido-[4,5-b]quinolines and [1,2,4]triazolo[2′,3′:3,4]pyrimido[6,5-b]quinolines." Medicinal Chemistry Research 22, no. 6 (2012): 2724–36. http://dx.doi.org/10.1007/s00044-012-0272-y.

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28

Xiao, Xiao, Bingxuan Shao, Jingyi Li, et al. "Correction: Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-b]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones." Chemical Communications 57, no. 35 (2021): 4331. http://dx.doi.org/10.1039/d1cc90146j.

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Correction for ‘Enantioselective synthesis of functionalized 1,4-dihydropyrazolo-[4′,3′:5,6]pyrano[2,3-b]quinolines through ferrocenyl-phosphine-catalyzed annulation of modified MBH carbonates and pyrazolones’ by Xiao Xiao et al., Chem. Commun., 2021, DOI: 10.1039/d1cc00989c.

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29

TAKEUCHI, Y., M. R. CHANG, K. HASHIGAKI, et al. "ChemInform Abstract: Synthesis and Antitumor Activity of Fused Quinoline Derivatives. Part 3. Novel N-Glycosylaminoindolo(3,2-b)quinolines." ChemInform 24, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199311220.

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30

Rádl, Stanislav, and Viktor Zikán. "Synthesis and biological activity of some basic-substituted 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinolines." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1812–19. http://dx.doi.org/10.1135/cccc19881812.

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Compounds Ia, Ib were obtained by an alkylation of 4,9-dihydro-6-hydroxy-1,3,9-trimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (VIIb) with the respective dialkylaminoalkyl chloride. The same alkylation of 4,9-dihydro-6-hydroxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (VIIIb) yielded compounds IIa and IIb. Similar alkylation of 4,9-dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (IXa) and its 6-methoxy derivative (IXb) afforded IIIa-IIId. Compound IV was prepared from 4-chloro-3-methyl-1H-pyrazolo[3,4-b]quinoline (Xa) via its 1-(3-dimethylaminopropyl)derivative (Xb). Compo

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31

Zhang, Hong, Yunhe Jiang, Xiaoxue Sun, Tianyu Liang, Xiang Wang, and Yang Li. "A new synthesis of indolo[2,3-b]quinolines from 3-acetyl-N-alkyl-2-chloroindoles with 2-aminobenzophenone." RSC Advances 14, no. 42 (2024): 30707–12. http://dx.doi.org/10.1039/d4ra05176a.

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A new synthesis of N-alkyl- and 11-phenyl-modified indolo[2,3-b]quinolines was achieved via PEG-400-promoted and visible light-induced one-step reaction of 3-acetyl-N-alkyl-2-chloroindoles with 2-aminobenzophenone in 40% methanol aqueous solution.

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32

Pokladko-Kowar, Monika, Ewa Gondek, Andrzej Danel, et al. "Trifluoromethyl Substituted Derivatives of Pyrazoles as Materials for Photovoltaic and Electroluminescent Applications." Crystals 12, no. 3 (2022): 434. http://dx.doi.org/10.3390/cryst12030434.

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New 6-CF3-1H-pyrazolo[3,4-b]quinolines with a methyl and/or phenyl group attached to the pyrazole core (Molx (x = 1, 2, 3, 4)) were synthesized and characterized in terms of their optoelectronic applications: photovoltaic and electroluminescence. The fluorescence emissions of the investigated phenyl-decorated pyrazoloquinolines is caused by the photoinduced charge transfer p process occurring between the phenyl substituent and the pyrazoloquinoline core, while 1,3-dimethyl-6-CF3-1H-pyrazolo[3,4-b]quinoline exhibits an π,π*-type emission. The number of phenyls and their substitution positions m

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33

Sharma, Shalabh, and Kuldeep Kumar Saxena. "Synthesis and Antibacterial Activity of Azetidinonyl Norfloxacin Congeners." International Journal of Pharmaceutical Sciences and Nanotechnology 8, no. 3 (2015): 2967–71. http://dx.doi.org/10.37285/ijpsn.2015.8.3.11.

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Some novel Schiff bases and azetidinone congeners of norfloxacin have been synthesized and screened for antibacterial activity. The structures of compounds 1-ethyl-6-fluoro-7-piperazinyl-4-oxo-3-(substitutedarylidinylcarboxy- hydrazido)quinolines (2-6) and 1-ethyl-6-fluoro-7-pipera-zinyl-4-oxo-3-(3′-choloro-2′-oxo-4′-substitutedaryl-3′-aze-tidinyl)-aminocarboxy quinolines (7-11) were established by spectral and elemental analysis. The compounds 2-11 were evaluated in vitro against various strains of bacteria: E. coli ATCC 25922, B. subtilis ATCC 1633 and S. aureus ATCC 25923 to determine their

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34

Henao, J. A., A. Palma, V. V. Kouznetsov, and J. M. Delgado. "X-ray powder diffraction data for two new N-substituted 3,4-dihydrospiro-2(1H) quinolines." Powder Diffraction 14, no. 4 (1999): 249–52. http://dx.doi.org/10.1017/s0885715600010617.

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The X-ray powder diffraction patterns for two N-substituted tetrahydroquinolines are reported. N-(α-Chloroacetyl)-6-methoxy-3,4-dihydro-4-methylspiro[cyclohexane-1′,2(1H)quinoline], C18H24ClNO2, and N-(α-chloroacetyl)-6-chloro-3,4-dihydro-4-methylspiro[cyclohexane-1′,2(1H)-quinoline], C17H21Cl2NO are monoclinic, with refined unit cell parameters a=1.4471(3), b=0.9600(4), c=1.1948(3) nm, β=93.21(2)°, V=1.6573(6) nm3, Z=4, Dx=1.29 gcm−3, and a=1.4487(3), b=0.9878(2), c=1.1390(2) nm, β=91.66(2)°, V=1.6294(4) nm3, Z=4, and Dx=1.32 gcm−3, respectively, with space group P21/n (No. 14).Key words: pow

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35

Hyland, Christopher J. T., Melissa J. Bird, Steven M. Wales, and Christopher Richardson. "Palladium-Catalyzed Decarboxylative Formal (4+2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles." Synlett 31, no. 09 (2020): 916–24. http://dx.doi.org/10.1055/s-0040-1707995.

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A diastereoselective palladium-catalyzed dearomative formal (4+2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5H-indolo[2,3-b]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.

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36

Muchowski, Joseph M., and Michael L. Maddox. "Concerning the mechanism of the Friedländer quinoline synthesis." Canadian Journal of Chemistry 82, no. 3 (2004): 461–78. http://dx.doi.org/10.1139/v03-211.

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Detailed experiments regarding the mechanism of the Friedländer synthesis of quinolines from o-aminobenzaldehydes and simple aldehydes or ketones are described. Under the basic or acidic conditions commonly used in this reaction, it is concluded that the first step involves a slow intermolecular aldol condensation of the aldehyde or ketone with the o-aminobenzaldehyde. The aldol adduct 5 generated in this manner then undergoes very rapid cyclization to 4, which subsequently loses water to produce the quinoline derivative 8. Both 5 and 4 are too short lived to be detectable (TLC), even when del

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37

Dabaeva, V. V., M. R. Bagdasaryan, and A. S. Noravyan. "Synthesis of 4-amino-4,8,9,10-tetrahydropyrimido[4′,3′:4,5]furo-[2,3-b]quinolines." Chemistry of Heterocyclic Compounds 43, no. 10 (2007): 1333–35. http://dx.doi.org/10.1007/s10593-007-0202-y.

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38

Khan, M. Musawwer, Saigal, Sarfaraz Khan, Sumbulunnisan Shareef, and Sahid Hussain. "A Facile and Green Approach for One-Pot Synthesis of Functionalized Chromeno[3, 4-b]quinolines and Spiro Chromeno[3, 4-b]quinolines by Using Molecular Iodine as a Catalyst." ChemistrySelect 3, no. 8 (2018): 2261–66. http://dx.doi.org/10.1002/slct.201702810.

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Rádl, Stanislav. "Preparation of Some Pyrazole Derivatives by Extrusion of Elemental Sulfur from 1,3,4-Thiadiazines." Collection of Czechoslovak Chemical Communications 57, no. 3 (1992): 656–59. http://dx.doi.org/10.1135/cccc19920656.

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In connection with our research of pyrazolo[3,4-b]quinolines we were also interested in the preparation of various pyrazole intermediates. In some cases we found a method useful based on extrusion of elemental sulfur from intermediate 1,3,4-thiadiazines. This short contribution describes the preparation of some new 3-anilino-4-pyrazolecarboxylic acid derivatives using this method.

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40

Orlov, V. D., and D. Yu Sidorenko. "Carbo[3 + 3] cyclocondensation reactions. A new method for the synthesis of tetrahydropyrazolo[1,5-b]quinazolines and tetrahydropyrazolo[4,5-b]quinolines." Chemistry of Heterocyclic Compounds 48, no. 4 (2012): 650–57. http://dx.doi.org/10.1007/s10593-012-1039-6.

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41

Nowacki, Michał, and Krzysztof Wojciechowski. "Transition-metal-free [3 + 3] annulation of indol-2-ylmethyl carbanions to nitroarenes. A novel synthesis of indolo[3,2-b]quinolines (quindolines)." Beilstein Journal of Organic Chemistry 14 (January 23, 2018): 194–202. http://dx.doi.org/10.3762/bjoc.14.14.

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Indol-2-ylmethyl carbanions stabilized by alkoxycarbonyl, cyano or benzenesulfonyl groups react with nitroarenes to form σH-adducts, which in the presence of base (triethylamine or DBU) and trimethylchlorosilane transform into indolo[3,2-b]quinoline derivatives in moderate to good yields.

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42

Li, Meng-Yuan, Hai-Wei Xu, Wei Fan, et al. "New formal (3+3) cycloaddition of enaminones for forming tetracyclic indolo[2,3-b]quinolines under microwave irradiation." Tetrahedron 70, no. 4 (2014): 1004–10. http://dx.doi.org/10.1016/j.tet.2013.11.022.

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43

Shiri, Morteza, Zeinab Faghihi, Hossein A. Oskouei, Majid M. Heravi, Shima Fazelzadeh, and Behrouz Notash. "The synthesis of iminothiophenone-fused quinolines and evaluation of their serendipitous reactions." RSC Advances 6, no. 95 (2016): 92235–40. http://dx.doi.org/10.1039/c6ra11469e.

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The novel synthesis of tricyclic 2-(cyclohexylimino)thieno[2,3-b]quinolin-3(2H)-ones from the reaction of 2-mercaptoquinoline-3-carbaldehydes and isocyanides in methanol without the use of any additive is described.

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44

Jnaneshwara, G. K., Nadim S. Shaikh, Neelam V. Bapat, and Vishnu H. Deshpande. "Selenium Dioxide: A Selective Oxidising Agent for the Functionalisation of Quinolines." Journal of Chemical Research 2000, no. 1 (2000): 34–35. http://dx.doi.org/10.3184/030823400103165590.

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45

Abd El-Aal, Hassan A. K., and Ali A. Khalaf. "Friedel–Crafts Chemistry. Part 46. Unprecedented Construction of Tricyclic Pyrazolo[3,4-b]quinolines, -[1,8]naphthyridines, -azepines, -azocines, -pyrido[3,2-g]azocines, and pyrazolo[3,4-b]azonines via Friedel–Crafts Ring Closures." Australian Journal of Chemistry 69, no. 6 (2016): 652. http://dx.doi.org/10.1071/ch15526.

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A series of keto-substituted pyrazolo[3,4-b]quinolines, pyrazolo[3,4-b][1,8]naphthyridines, benzo[e]pyrazolo[3,4-b]azepines, benzo[g]pyrazolo[3,4-b]azocines, pyrazolo[3,4-b]pyrido[3,2-g]azocines, and benzo[g]pyrazolo[3,4-b]azonines scaffolds were synthesized via a Friedel–Crafts cyclialkylation approach. The precursor acids were obtained by utilizing the modified Ullman coupling reactions of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid with different aryl amines followed by ring closures in the presence of AlCl3/CH3NO2 or P2O5 or polyphosphoric acid catalysts. Particular attention

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46

Milata, Viktor, and Dušan Ilavský. "Thermal cyclocondensations of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino derivatives of 2-propenoic acid." Collection of Czechoslovak Chemical Communications 52, no. 12 (1987): 2918–25. http://dx.doi.org/10.1135/cccc19872918.

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The cyclization of 3-N(4- and 5-benzimidazolyl and benztriazolyl)amino-2-cyano- and 2-ethoxycarbonyl-2-propenoate esters Ia, b-IVa, b under the conditions of the Gould-Jacobs reaction leads to angularly ring-fused substituted imidazo or triazolo[4,5-f] (V, VI) and [4,5-h] (VII, VIII) quinolines, respectively. The esters Vb-VIIIb have been transformed into the corresponding chloroderivatives Vc-VIIIc. 3-N(5-Benzimidazolyl and 5-benztriazolyl)amino-2-cyano-2-propenenitriles are cyclized in the presence of aluminium(III) chloride to give the aminoquinolines Vd, VId. The structure of the products

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47

Orlov, V. D., and D. Yu Sidorenko. "ChemInform Abstract: Carbo[3 + 3] Cyclocondensation Reactions. A New Method for the Synthesis of Tetrahydropyrazolo[1,5-b]quinazolines and Tetrahydropyrazolo[4,5-b]quinolines." ChemInform 43, no. 51 (2012): no. http://dx.doi.org/10.1002/chin.201251137.

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Ahmed, Abd-El Hamid. "SYNTHESIS OF CERTAIN 8-[2-HYDROXY-3-(SUBSTITUTEDAMINO)PROPOXY]QUINOLINES AS B-ADRENERGIC BLOCKING AGENTS." Bulletin of Pharmaceutical Sciences. Assiut 15, no. 1 (1992): 83–88. http://dx.doi.org/10.21608/bfsa.1992.70218.

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Pokladko, M., E. Gondek, J. Sanetra, et al. "Spectral emission properties of 4-aryloxy-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinolines." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 73, no. 2 (2009): 281–85. http://dx.doi.org/10.1016/j.saa.2009.02.026.

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REISCH, J., and P. NORDHAUS. "ChemInform Abstract: Acetylene Chemistry. Part 33. Synthesis of 2-Substituted Dihydrofuro(2, 3-b)quinolines." ChemInform 25, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199424258.

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