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Journal articles on the topic 'Dihydroquinoline'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Forrest, T. P., G. A. Dauphinee, and S. A. Deraniyagala. "On the mechanism of disproportionation reactions of 1,2-dihydroquinolines." Canadian Journal of Chemistry 63, no. 2 (1985): 412–17. http://dx.doi.org/10.1139/v85-068.

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The commonly accepted mechanism for the acid-catalyzed disproportionation of 1,2-dihydroquinolines involves a hydride transfer from C-2 of one dihydroquinoline molecule to C-4 of another molecule which has already been protonated at C-3. This mechanism is shown to be incorrect. The proposed intermediate is shown to react by solvent addition and not by reduction under the conditions of the reaction. Evidence has been obtained which shows that the reaction proceeds by way of a 3,4-dihydroquinoline intermediate. A possible mechanism for the formation of the intermediate is discussed.

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2

VOSTRIKOVA, Tatiana V., Vladislav N. KALAEV, Svetlana M. MEDVEDEVA, Nadezhda P. NOVICHIKHINA, and Khidmet S. SHIKHALIEV. "SYNTHESIZED ORGANIC COMPOUNDS AS GROWTH STIMULATORS FOR WOODY PLANTS." Periódico Tchê Química 17, no. 35 (2020): 327–37. http://dx.doi.org/10.52571/ptq.v17.n35.2020.29_vostrikova_pgs_327_337.pdf.

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The effect of synthesized organic compounds of 6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline, its derivatives, and hydrogenated analogs on the height of seedlings of ornamental woody plants was studied. The height of seedlings as a morphometric parameter was measured 7 months after the start of the experiment. The pre-sowing seed treatment of Rhododendron ledebourii and Rhododendron smirnowii, with the studied compounds, demonstrated that dihydro- and tetrahydroquinoline with the concentration of 0.1% proved to be the most efficient. Dihydroquinolines at concentrations of 0.05 and 0.1% proved

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3

Marchand, Guillaume, Nathalie Wambang, Sylvain Pellegrini, et al. "Effects of Ferrocenyl 4-(Imino)-1,4-Dihydro-quinolines on Xenopus laevis Prophase I - Arrested Oocytes: Survival and Hormonal-Induced M-Phase Entry." International Journal of Molecular Sciences 21, no. 9 (2020): 3049. http://dx.doi.org/10.3390/ijms21093049.

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Xenopus oocytes were used as cellular and molecular sentinels to assess the effects of a new class of organometallic compounds called ferrocenyl dihydroquinolines that have been developed as potential anti-cancer agents. One ferrocenyl dihydroquinoline compound exerted deleterious effects on oocyte survival after 48 h of incubation at 100 μM. Two ferrocenyl dihydroquinoline compounds had an inhibitory effect on the resumption of progesterone induced oocyte meiosis, compared to controls without ferrocenyl groups. In these inhibited oocytes, no MPF (Cdk1/cyclin B) activity was detected by wester

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4

VOSTRIKOVA, Tatiana V., Vladislav N. KALAEV, Andrey Yu POTAPOV, MICHAIL A. POTAPOV, and Khidmet S. SHIKHALIEV. "USE OF NEW COMPOUNDS OF THE QUINOLINE SERIES AS EFFECTIVE STIMULANTS OF GROWTH PROCESSES." Periódico Tchê Química 17, no. 35 (2020): 781–90. http://dx.doi.org/10.52571/ptq.v17.n35.2020.66_vostrikova_pgs_781_790.pdf.

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The results of a study of the action of compounds of the general formula: 1-alkyl-2,2,4-trimethyl-6-aminocarbothioyl-1,2-dihydroquinoline and 1-alkyl-2,2,4-trimethyl-6-aminocarbothioyl-1,2,3,4-tetrahydroquinoline are presented. The most effective growth stimulants from compounds of the series 1-alkyl-2,2,4-trimethyl-6-aminocarbothioyl-1,2-dihydroquinoline and 1-alkyl-2,2,4-trimethyl-6-aminocarbothioyl-1,2,3,4-tetrahydroquinoline for yellow rhododendron (Rhododendron luteum) and Ledebur rhododendron (Rhododendron ledebourii) were revealed. Rhododendron seedlings were counted to study laboratory

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5

Vostrikova, Tatiana, Vladislav Kalaev, Svetlana Medvedeva, Irina Ledeneva, and Khidmet Shikhaliev. "Quinoline Derivatives as Growth Regulators for Ornamental Plants." Southern Brazilian Journal of Chemistry 28, no. 28 (2020): 10–16. http://dx.doi.org/10.37633/sbjc.28(28)2020.10-16.

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It is investigated the effect of synthesized organic compounds of 6-hydroxy-2,2,4-trimethyl-1,2- dihydroquinoline, its derivatives, and hydrogenated analogs. These compounds affected the height of seedlings when they were used for pre-sowing seed treatment of the following ornamental plants: annual ornamental grass – scarlet sage (Salvia splendens) and woody plant – yellow rhododendron (Rhododendron luteum). Prior to the sprouting process, the seeds of Rh. luteum and S. splendens were soaked in water solutions of compounds with concentrations of 0.01%, 0.05%, and 0.1% for 18 hours. Dihydro- an

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6

V. VOSTRIKOVA, Tatiana, Vladislav N. KALAEV, Svetlana M. MEDVEDEVA, Irina V. LEDENEVA, and Khidmet S. SHIKHALIEV. "QUINOLINE DERIVATIVES AS GROWTH REGULATORS FOR ORNAMENTAL PLANTS." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 28, no. 28 (2020): 10–16. http://dx.doi.org/10.48141/sbjchem.v28.n28.2020.02_vostrikova_pgs_10_16.pdf.

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It is investigated the effect of synthesized organic compounds of 6-hydroxy-2,2,4-trimethyl-1,2- dihydroquinoline, its derivatives, and hydrogenated analogs. These compounds affected the height of seedlings when they were used for pre-sowing seed treatment of the following ornamental plants: annual ornamental grass – scarlet sage (Salvia splendens) and woody plant – yellow rhododendron (Rhododendron luteum). Prior to the sprouting process, the seeds of Rh. luteum and S. splendens were soaked in water solutions of compounds with concentrations of 0.01%, 0.05%, and 0.1% for 18 hours. Dihydro- an

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7

Chinh, Pham The, Pham Thi Tham, Duong Huong Quynh, et al. "Synthesis and Cytotoxic Activity of Several Novel N-Alkyl-Plinabulin Derivatives With Aryl Group Moieties." Natural Product Communications 16, no. 4 (2021): 1934578X2110100. http://dx.doi.org/10.1177/1934578x211010040.

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Seven novel N-alkyl-plinabulin derivatives with aryl groups moieties (nitroquinoline, 1,4-dihydroquinoline, 4-methoxybenzene, and 4-chlorobenzene) have been synthesized via aldol condensation and alkylation in one-pot, and tested for their cytotoxicity against 4 cancer cell lines (KB, HepG2, Lu, and MCF7). Compounds ( Z)−3-((6,8-dimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)piperazine-2,5-dione (5a), ( Z)−6-(( Z)−4-methoxybenzylidene)−1-(prop-2-yn-1-yl)−3-((1,6,8-trimethyl-4-oxo-1,4-dihydroquinolin-2-yl)methylene)piperazine-2,5-dione (5b), a

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8

Hradil, Pavel, Lubomír Kvapil, Jan Hlaváč, Karel Lemr, and Juraj Ševčík. "Cyclization of Phenacyl 2-{[2,2-Di(ethoxycarbonyl)vinyl]amino}benzoate." Collection of Czechoslovak Chemical Communications 63, no. 4 (1998): 520–24. http://dx.doi.org/10.1135/cccc19980520.

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Reaction of phenacyl anthranilate (1) with diethyl (ethoxymethylidene)malonate afforded phenacyl 2-{[2,2-di(ethoxycarbonyl)vinyl]amino}benzoate (2) which on heating in polyphosphoric acid underwent degradation. Thermal cyclization of 2 in diphenyl ether gave phenacyl 3-(ethoxycarbonyl)-4-oxo-1,4-dihydroquinoline-8-carboxylate (4). The phenacyl group did not cyclize even on prolonged heating at 250 °C. Heating in sulfuric acid resulted in hydrolysis of the ethyl ester under formation of 4-oxo-8-[(phenacyloxy)carbonyl]-1,4-dihydroquinoline-3-carboxylic acid (6). The structure of 4 was confirmed

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9

Gaber, Ahmed, Walaa F. Alsanie, Majid Alhomrani, Abdulhakeem S. Alamri, Ibrahim M. El-Deen, and Moamen S. Refat. "Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity." Crystals 11, no. 5 (2021): 571. http://dx.doi.org/10.3390/cryst11050571.

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This research aimed to produce new 1-[(aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic acid derivatives and check their anticancer effect against the breast cancer MCF-7 cell line. The 2-oxo-1,2-dihydroquinoline-3-carboxylic acid (4) compound was obtained by hydrolyzing ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylate (2) with thiourea and anhydrous potassium carbonate ethanol, which was then treated with ethyl 3-substituted 2-cyanoacrylates (6) in the presence of triethylamine in diethyl formamide to give 1-[2-(ethoxy)carbonyl-2-cyano-1-arylvinyl]-2-oxo

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10

Menichetti, Andrea, Francesco Berti, Lorenzo Guazzelli, et al. "Organocatalytic alkylation of carbohydrate-containing aldehydes with dihydroquinoline N,O-acetals: Absolute configuration of 1,2-dihydroquinolines." Chirality 31, no. 2 (2018): 127–37. http://dx.doi.org/10.1002/chir.23036.

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11

Tao, Le-Yi, Yin Wei, and Min Shi. "Dimerization–cyclization reactions of isocyanoaryl-tethered alkylidenecyclobutanes via a triplet biradical mediated process." Organic Chemistry Frontiers 7, no. 18 (2020): 2634–43. http://dx.doi.org/10.1039/d0qo00878h.

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A triplet biradical mediated dimerization–cyclization reaction of isocyanoaryl-tethered alkylidenecyclobutanes to construct macrocyclic skeletons including dihydroquinoline and quinoline units has been reported.

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12

Mokar, Bhanudas Dattatray, Prakash D. Jadhav, Y. B. Pandit та Rai-Shung Liu. "Gold-catalyzed (4 + 2)-annulations between α-alkyl alkenylgold carbenes and benzisoxazoles with reactive alkyl groups". Chemical Science 9, № 19 (2018): 4488–92. http://dx.doi.org/10.1039/c8sc00986d.

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13

Vijay, K., C. Nandi, and Shriniwas D. Samant. "Synthesis of a dihydroquinoline based fluorescent cyanine for selective, naked eye, and turn off detection of Fe3+ions." RSC Advances 6, no. 55 (2016): 49724–29. http://dx.doi.org/10.1039/c6ra06642a.

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14

Nekipelova, Tatiana D., Evgenii N. Khodot, Olga N. Klimovich (Lygo), Lidiya N. Kurkovskaya, Irina I. Levina, and Vladimir A. Kuzmin. "Novel hetarylazo dyes containing tetrazole and hydroquinoline moieties: spectral characteristics, solvatochromism and photochemistry." Photochemical & Photobiological Sciences 15, no. 12 (2016): 1558–66. http://dx.doi.org/10.1039/c6pp00251j.

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Novel hetarylazo dyes containing tetrazole and tetra- or dihydroquinoline moieties exhibit solvatochromism dramatically depending on the proton accepting ability of solvents and the dye concentration.

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15

Yu, Yan, Man-Su Tu, Bo Jiang, Shu-Liang Wang, and Shu-Jiang Tu. "Multicomponent synthesis of polysubstituted dihydroquinoline derivatives." Tetrahedron Letters 53, no. 38 (2012): 5071–75. http://dx.doi.org/10.1016/j.tetlet.2012.07.008.

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16

Kato, K., H. Morikawa, H. Kimoto, and K. Momota. "5,5,8,8-Tetrafluoro-6-methoxy-5,8-dihydroquinoline." Acta Crystallographica Section C Crystal Structure Communications 52, no. 11 (1996): 2836–37. http://dx.doi.org/10.1107/s0108270196007676.

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17

Graham, D., and A. R. Kennedy. "7-Methoxy-2,2,4-trimethyl-1,2-dihydroquinoline." Acta Crystallographica Section C Crystal Structure Communications 54, no. 7 (1998): 978–80. http://dx.doi.org/10.1107/s0108270198001577.

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18

Balayer, A., T. Sévenet, H. Schaller, et al. "Dihydroquinoline-type Alkaloids fromBhesa Paniculata, Celastraceae." Natural Product Letters 2, no. 1 (1993): 61–67. http://dx.doi.org/10.1080/10575639308043456.

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19

Batalha, Pedro N., Luana da S. M. Forezi, Maria Clara R. Freitas, et al. "Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide." Beilstein Journal of Organic Chemistry 15 (February 12, 2019): 388–400. http://dx.doi.org/10.3762/bjoc.15.35.

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4-Oxoquinolines are a class of organic substances of great importance in medicinal chemistry, due to their biological and synthetic versatility. N-1-Alkylated-4-oxoquinoline derivatives have been associated with different pharmacological activities such as antibacterial and antiviral. The presence of a carboxamide unit connected to carbon C-3 of the 4-oxoquinoline core has been associated with various biological activities. Experimentally, the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide occurs at the nitrogen of the oxoquinoline group, in a regiosselective way. I

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20

Kovalenko, Drushlyak, Konovalova, et al. "Novel One-Pot Synthesis of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic and Crystallographic Studies." Molbank 2019, no. 4 (2019): M1085. http://dx.doi.org/10.3390/m1085.

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A new suitable method of synthesis of methyl 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by condensation of methyl 2-isothiocyanatobenzoate and methyl malonate is described. The structure of the compound both and by-product methyl 2(methoxycarbonothioylamino)benzoate was confirmed by means of elemental analysis, 1H NMR, 13C NMR, LC/MS and single crystal X-ray diffraction. UV/Vis and IR spectra of compounds are described. The presence of a strong intramolecular hydrogen bond between the hydroxy group and the carbonyl oxygen atom of the ester group in methyl 4-hydroxy-2-thioxo-1,2-dihy

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21

Holman, Michelle A., Natalie M. Williamson, and A. David Ward. "Preparation and Cyclization of Some N-(2,2-Dimethylpropargyl) Homo- and Heteroaromatic Amines and the Synthesis of Some Pyrido[2,3-d]pyrimidines." Australian Journal of Chemistry 58, no. 5 (2005): 368. http://dx.doi.org/10.1071/ch04260.

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The Cu(i) catalyzed cyclization of o-substituted N-(2,2-dimethylpropargyl)anilines yields 8-substituted 2,2-dimethyl-1,2-dihydroquinolines, while m-substituted analogues provide a mixture of 5- and 7-substituted dihydroquinoline systems. This reaction can be extended to 2-amino-N-(2,2-dimethylpropargyl)anthracene, yielding a dihydronaphtho[2,3-f]quinoline product, and to aminoquinoline derivatives, which yield substituted phenanthroline products. Pyridine analogues did not cyclize, apparently because of complexation with the copper reagent. An alternative synthetic approach to these cyclized p

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22

Yernale, Nagesh Gunvanthrao, and Mruthyunjayaswamy Bennikallu Hire Mathada. "Synthesis, Characterization, Antimicrobial, DNA Cleavage, andIn VitroCytotoxic Studies of Some Metal Complexes of Schiff Base Ligand Derived from Thiazole and Quinoline Moiety." Bioinorganic Chemistry and Applications 2014 (2014): 1–17. http://dx.doi.org/10.1155/2014/314963.

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A novel Schiff base ligandN-(4-phenylthiazol-2yl)-2-((2-thiaxo-1,2-dihydroquinolin-3-yl)methylene)hydrazinecarboxamide(L)obtained by the condensation ofN-(4-phenylthiazol-2-yl)hydrazinecarboxamide with 2-thioxo-1,2-dihydroquinoline-3-carbaldehyde and its newly synthesized Cu(II), Co(II), Ni(II), and Zn(II) complexes have been characterized by elemental analysis and various spectral studies like FT-IR,1H NMR, ESI mass, UV-Visible, ESR, TGA/DTA, and powder X-ray diffraction studies. The Schiff base ligand(L)behaves as tridentate ONS donor and forms the complexes of type [ML(Cl)2] with square pyr

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23

Moussaoui, Oussama, El Mestafa El Hadrami, Ghita Benjalloune Touimi, et al. "Synthesis of a new serie of quinoline-carboxamides based on methylated aminoesters: NMR characterization and antimicrobial activity." Mediterranean Journal of Chemistry 9, no. 4 (2019): 326–36. http://dx.doi.org/10.13171/mjc941911231077sc.

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Ten new quinoline-carboxamides have been synthesized using the coupling reaction between 2-oxo-1,2-dihydroquinoline-4-carboxylic acid as a substrate and five different amino ester at room temperature with basic media (triethylamine). The products were obtained with a good yield ranging from 60 to 80 % and were structurally characterized by 1H and 13C NMR spectroscopy and mass spectrometry. The antibacterial activities of the synthesized compounds have been evaluated against 9 strains of bacteria and compared to references (erythromycin, ofloxacin, ticarcillin, oxacillin, ampicillin, norfloxaci

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24

Heravi, Majid M., Zeinab S. Jaddi, Hossein A. Oskooie, Shahnaz Khaleghi, and Mitra Ghassemzadeh. "Regioselective Synthesis of Quinolone Antibacterials via Borate Complex of Quinolone Carboxylic Acid." Journal of Chemical Research 2005, no. 9 (2005): 578–79. http://dx.doi.org/10.3184/030823405774308943.

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1-substituted 7-chloro-6-fluoro-4-oxo-1,2-dihydroquinoline-3-carboxylic acids were converted to borate complexes. These compounds were treated with piperazine in presence of triethylamine to afford ciprofloxacin and norfloxacin in high yields.

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25

Evans, Paul, Ronald Grigg, and Michael Monteith. "Metathesis of aniline and 1,2-dihydroquinoline derivatives." Tetrahedron Letters 40, no. 28 (1999): 5247–50. http://dx.doi.org/10.1016/s0040-4039(99)00993-4.

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26

Rybakov, Victor B., Vladimir V. Chernyshev, Igor V. Ukrainets, Peter A. Bezugly, Lyudmila V. Sidorenko, and Nicola Skaif. "4-(4-Ethoxyphenylamino)-2-oxo-1,2-dihydroquinoline." Acta Crystallographica Section E Structure Reports Online 57, no. 8 (2001): o721—o722. http://dx.doi.org/10.1107/s160053680101100x.

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27

Gültekin, Zeynep, Wolfgang Frey, Barış Tercan, and Tuncer Hökelek. "Dimethyl 2,6,8-trimethyl-1,2-dihydroquinoline-2,4-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 66, no. 11 (2010): o2891—o2892. http://dx.doi.org/10.1107/s160053681004153x.

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28

Ukhin, Lev Yu, and Zhanna I. Orlova. "A Novel Synthesis of 1,2-Dihydroquinoline Derivatives." Mendeleev Communications 5, no. 6 (1995): 234–35. http://dx.doi.org/10.1070/mc1995v005n06abeh000543.

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29

Gültekin, Zeynep, Wolfgang Frey, Barış Tercan, and Tuncer Hökelek. "Dimethyl 2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 67, no. 3 (2011): o672—o673. http://dx.doi.org/10.1107/s1600536811005605.

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30

Hodík, Tomáš, and Christoph Schneider. "Brønsted acid-catalyzed, enantioselective synthesis of 1,4-dihydroquinoline-3-carboxylates via in situ generated ortho-quinone methide imines." Organic & Biomolecular Chemistry 15, no. 17 (2017): 3706–16. http://dx.doi.org/10.1039/c7ob00488e.

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A straightforward approach toward the synthesis of a broad range of 1,4-dihydroquinoline-3-carboxylates is described. Under phosphoric acid catalysis in situ-generated ortho-quinone methide imines reacted with β-keto esters to form the nitrogen heterocycles with good chemical yields and enantioselectivities.

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31

Brazhnikov, D. A., T. N. Popova, E. D. Kryl`skii, et al. "Effect of 6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline on the intensity of free radical processes and the activity of oxidative metabolism enzymes under toxic liver injury in rats." Biomeditsinskaya Khimiya 65, no. 4 (2019): 331–38. http://dx.doi.org/10.18097/pbmc20196504331.

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The effect of 6-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline on markers of hepatocytes cytolysis (aspartate aminotransferase, alanine aminotransferase and gamma-glutamyl transpeptidase), parameters reflecting the state of oxidative status (intensity of biochemical luminescence and the content of diene conjugates), and the activity of oxidative metabolism enzymes (aconitate hydratase, glucose-6-phosphate dehydrogenase, NADP-isocitrate dehydrogenase) was studied in rats with CCl4-induced liver injury. The results obtained in the course of the work demonstrated the ability of the test compound to

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32

Yu, Yan, Man-Su Tu, Bo Jiang, Shu-Liang Wang, and Shu-Jiang Tu. "ChemInform Abstract: Multicomponent Synthesis of Polysubstituted Dihydroquinoline Derivatives." ChemInform 43, no. 52 (2012): no. http://dx.doi.org/10.1002/chin.201252135.

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33

Güngör, Füsun Şeyma, Olcay Anaç, and Özkan Sezer. "Synthesis of the Naphthalenone, Dihydroquinoline, and Dihydrofuran Derivatives." Helvetica Chimica Acta 94, no. 6 (2011): 1115–29. http://dx.doi.org/10.1002/hlca.201000386.

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34

Evans, Paul, Ronald Grigg, and Michael Monteith. "ChemInform Abstract: Metathesis Aniline and 1,2-Dihydroquinoline Derivatives." ChemInform 30, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199941134.

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35

Ladraa, Souheila, Abdelmalek Bouraiou, Sofiane Bouacida, Thierry Roisnel, and Ali Belfaitah. "5,8-Dimethoxy-2-phenyl-1,4-dihydroquinoline-3-carbonitrile." Acta Crystallographica Section E Structure Reports Online 66, no. 9 (2010): o2312—o2313. http://dx.doi.org/10.1107/s1600536810031685.

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36

Lukyanov, B. S., M. B. Lukyanova, and N. V. Volbushko. "Photoconversions of 1-Acetyl-2,2,4-trimethyl[2H]dihydroquinoline." Chemistry of Heterocyclic Compounds 41, no. 7 (2005): 936–37. http://dx.doi.org/10.1007/s10593-005-0253-x.

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37

Kovalenko, Sergiy M., Oleksandr G. Drushlyak, Svitlana V. Shishkina, et al. "Methylation of Methyl 4-Hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate: Synthetic, Crystallographic, and Molecular Docking Studies." Molecules 25, no. 18 (2020): 4238. http://dx.doi.org/10.3390/molecules25184238.

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Consecutive alkylation of 4-hydroxy-2-thioxo-1,2-dihydroquinoline-3-carboxylate by CH3I has been investigated to establish regioselectivity of the reaction for reliable design and synthesis of combinatorial libraries. In the first stage, the product of S-methylation-methyl 4-hydroxy-2-(methylthio)quinoline-3-carboxylate was obtained. The subsequent alkylation with CH3I led to the formation of both O- and N-methylation products mixture-methyl 4-methoxy-2-(methylthio)quinoline-3-carboxylate and methyl 1-methyl-2-(methylthio)-4-oxo-1,4-dihydroquinoline-3-carboxylate with a predominance of O-methy

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38

Kingsbury, Alex, Steve Brough, Antonio Pedrina McCarthy, William Lewis, and Simon Woodward. "Conjugate Addition Routes to 2-Alkyl-2,3-dihydroquinolin-4(1H )-ones and 2-Alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates." European Journal of Inorganic Chemistry 2020, no. 11-12 (2019): 1011–17. http://dx.doi.org/10.1002/ejic.201901036.

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39

Bohnert, Sabine, and Wolf-H. Gündel. "Redoxreaktionen mit cyclopeptidartigen Chinolinderivaten als lipophil-maskierte NAD-Modellverbindungen / Redox Reactions with Cyclopeptide-Like Quinoline Derivatives as Lipophilic NAD Model Compounds." Zeitschrift für Naturforschung B 42, no. 9 (1987): 1159–66. http://dx.doi.org/10.1515/znb-1987-0917.

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Quaternary salts of the amides of N-(3-quinolinecarbonyl) amino acids (7) cyclise under the influence of base to give fourteen membered rings (9). This dimerisation is a reaction with high diastereoselectivity. The addition product 9 can be regarded as lipophilic, masked NAD model compound: 9 oxidizes 2-propanol under ZnCl2 catalysis to give in high yield acetone and the 1.4-dihydroquinoline.

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Yorimitsu, Hideki, Hiroki Yamagishi, Shun Tsuchiya, Hayate Saito, Keisuke Nogi, and Jun Shimokawa. "Four-Component Coupling Strategy for 2,3,4-Trisubstituted 3,4-Dihydroquinoline." HETEROCYCLES 99, no. 1 (2019): 301. http://dx.doi.org/10.3987/com-18-s(f)24.

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Garudachari, B., Arun M. Islor, M. N. Satyanarayan, Thomas Gerber, Eric Hosten, and Richard Betz. "Ethyl 4-oxo-8-trifluoromethyl-1,4-dihydroquinoline-3-carboxylate." Acta Crystallographica Section E Structure Reports Online 68, no. 12 (2012): o3304—o3305. http://dx.doi.org/10.1107/s1600536812045321.

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Rybakov, Victor B., Vladimir V. Chernyshev, Igor V. Ukrainets, Peter A. Bezugly, Lyudmila V. Sidorenko, and Nicola Skaif. "Methyl 4-amino-2-oxo-1,2-dihydroquinoline-3-carboxylate." Acta Crystallographica Section E Structure Reports Online 59, no. 4 (2003): o412—o414. http://dx.doi.org/10.1107/s1600536803004379.

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Kanchanadevi, J., G. Anbalagan, V. Saravanan, A. K. Mohanakrishnan, and V. Manivannan. "2-(4-Methylphenyl)-1-phenylsulfonyl-3-nitro-1,2-dihydroquinoline." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2225. http://dx.doi.org/10.1107/s1600536811030455.

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UKHIN, L. YU, and Z. I. ORLOVA. "ChemInform Abstract: A Novel Synthesis of 1,2-Dihydroquinoline Derivatives." ChemInform 27, no. 16 (2010): no. http://dx.doi.org/10.1002/chin.199616170.

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Lee, Hyun Joo, Da Eun Lee, and Dae Young Kim. "Thiourea-catalyzed Intramolecular Allylic Amination: Synthesis of Dihydroquinoline Derivatives." Bulletin of the Korean Chemical Society 36, no. 1 (2015): 370–73. http://dx.doi.org/10.1002/bkcs.10014.

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Thinagar, S., D. Velmurugan, V. Rajakannan, Il-Hwan Suh, and S. Akila. "4-Chloro-2-(4-chlorophenyl)-1-formyl-1,2-dihydroquinoline." Acta Crystallographica Section E Structure Reports Online 58, no. 8 (2002): o893—o895. http://dx.doi.org/10.1107/s1600536802012588.

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Keleşoğlu, Zeynep, Zeynep Gültekin, and Orhan Büyükgüngör. "Dimethyl 8-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 67, no. 3 (2011): o544—o545. http://dx.doi.org/10.1107/s1600536811003564.

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Gültekin, Zeynep, Wolfgang Frey, and Tuncer Hökelek. "Dimethyl 5,6,7-trimethoxy-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 67, no. 3 (2011): o576. http://dx.doi.org/10.1107/s1600536811004028.

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Gültekin, Zeynep, Wolfgang Frey, and Tuncer Hökelek. "Dimethyl 6-iodo-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate." Acta Crystallographica Section E Structure Reports Online 69, no. 9 (2013): o1476. http://dx.doi.org/10.1107/s1600536813023544.

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Ishikawa, Yoshinobu, and Nanako Yoshida. "Ethyl 8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (2014): o719. http://dx.doi.org/10.1107/s1600536814011854.

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Abstract:

In the title compound, C13H13NO4, the asymmetric unit contains four independent molecules, each exhibiting an intramolecular N—H...O hydrogen bond. The ethyl group in one of the four molecules is disordered, with a refined occupancy ratio of 0.295 (16):0.705 (16). A face-to-face stacking interaction is found between the benzene rings of the quinoline units of two of the molecules [centroid–centroid distance = 3.541 (2) Å], which are sandwiched by the other two molecules through N—H...O hydrogen bonding. In the crystal, the sandwiched molecules are assembledviastacking interactions along theb-a

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