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Journal articles on the topic '5-c]isoquinolines'

Author: Grafiati

Published: 4 June 2021

Last updated: 12 February 2022

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1

Deprets, Stephanie, and Gilbert Kirsch. "ChemInform Abstract: Synthesis of 5-Methylbenzo[b]thieno[2,3-c]isoquinolines and 5-Methylbenzo[b]seleno[2,3-c]isoquinolines." ChemInform 31, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.200025155.

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2

Deprets, Stéphanie, and Gilbert Kirsch. "Synthesis of 5-Methylbenzo[b]thieno[2,3-c]isoquinolines and5-Methylbenzo[b]seleno[2,3-c]isoquinolines." European Journal of Organic Chemistry 2000, no. 7 (2000): 1353–57. http://dx.doi.org/10.1002/1099-0690(200004)2000:7<1353::aid-ejoc1353>3.0.co;2-a.

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3

Yugandar, Somaraju, and Hiroyuki Nakamura. "Rhodium(iii)-catalysed carboxylate-directed C–H functionalizations of isoxazoles with alkynes." Chemical Communications 55, no. 58 (2019): 8382–85. http://dx.doi.org/10.1039/c9cc03283e.

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Isoxazolyl-4-carboxylic acids underwent rhodium(iii)-catalysed carboxylate-directed C–H functionalizations with internal alkynes to produce pyranoisoxazolones, isoquinolines, and 5-alkenylisoxazoles controlled by oxidants.

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4

Bogza, Sergei L., Anna A. Malienko, Sergei Y. U. Sujkov, et al. "Convenient one pot synthesis of 5-unsubstituted pyrazolo [3,4-c]isoquinolines." Journal of Heterocyclic Chemistry 38, no. 2 (2001): 523–25. http://dx.doi.org/10.1002/jhet.5570380238.

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5

Zhang, Bo, and Armido Studer. "1-Trifluoromethylated isoquinolines via radical trifluoromethylation of isonitriles." Org. Biomol. Chem. 12, no. 48 (2014): 9895–98. http://dx.doi.org/10.1039/c4ob02145b.

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A simple and efficient approach to biologically important 1-trifluoroalkylated isoquinolines starting with readily prepared β-aryl-α-isocyano-acrylates and R<sub>f</sub>-I(iii)-reagents (R<sub>f</sub> = CF<sub>3</sub>, C<sub>2</sub>F<sub>5</sub>, C<sub>3</sub>F<sub>7</sub>) is described.

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6

Hejsek, Miloslav, Jan Slouka, Vojtěch Bekárek, and Antonín Lyčka. "Cyclization Reactions of 2-(6-Azauracil-5-yl)benzoic Acid and Some Its Derivatives." Collection of Czechoslovak Chemical Communications 57, no. 1 (1992): 123–33. http://dx.doi.org/10.1135/cccc19920123.

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2-(6-Azauracil-5-yl)benzoic acid (Ib) and its thio analogue Ia give new heterocyclic compounds, 1,2-dihydro-1,2,4-triazino[5,6-c]isocoumarin-3-one (IVb) and analogous 3-thione IVa, respectively, on treatment with N,N'-dicyclohexylcarbodiimide. A series of substituted 1,2,4-triazino[5,6-c]isoquinolines V-XVI have been prepared from these compounds and from other functional derivatives (II, III) of the acids I.

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7

Bogza, Sergei L., Konstantin I. Kobrakov, Anna A. Malienko, et al. "ChemInform Abstract: Convenient One Pot Synthesis of 5-Unsubstituted Pyrazolo[3,4-c]isoquinolines." ChemInform 32, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.200135148.

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8

Kalugin, V. E., and A. M. Shestopalov. "Synthesis of substituted 5-aminobenzothieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives." Russian Chemical Bulletin 64, no. 4 (2015): 878–82. http://dx.doi.org/10.1007/s11172-015-0948-9.

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9

Lantos, Ivan, and Haralambos E. Katerinopoulos. "Synthetic transformations of cyclopropyl annulated dihydroisoquinolines." Canadian Journal of Chemistry 69, no. 6 (1991): 1033–37. http://dx.doi.org/10.1139/v91-152.

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Isomeric 3-cyano-3-methyl-2-acetyl-cycloprop[c]isoquinolines, 5 and 6, were prepared by alkylation and cyclopropanation of Reissert compounds and their reactions under basic conditions were examined. Both compounds, under the influence of methoxide, yielded isoquinoline derived products resulting from cleavage of the peripheral C—C bond. The results are postulated to derive from attack of the methoxide on the acyl carbonyl, forming a tetrahedral adduct that undergoes ring opening. Key words: cyclopropanation, ring opening, tetrahedral complex, pyramidalization.

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10

Chen, Lu, Xian Zhang, Bin Chen, Bin Li, and Yibiao Li. "Synthesis of benzo[4, 5]imidazo[2,1-a]isoquinolines via intramolecular C–H bond functionalization." Chemistry of Heterocyclic Compounds 53, no. 5 (2017): 618–21. http://dx.doi.org/10.1007/s10593-017-2101-1.

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11

Wang, Dingyi, Rongxing Zhang, Ruihong Deng, Sen Lin, Shengmei Guo, and Zhaohua Yan. "Copper-Mediated Oxidative Functionalization of C(sp3)–H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones." Journal of Organic Chemistry 81, no. 22 (2016): 11162–67. http://dx.doi.org/10.1021/acs.joc.6b02145.

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12

Döpp, Dietrich, Sabine Jüschke, and Gerald Henkel. "Dicyanomethylene Compounds as Cyanation Reagents." Zeitschrift für Naturforschung B 57, no. 4 (2002): 460–70. http://dx.doi.org/10.1515/znb-2002-0412.

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Ethenetetracarbonitrile (2, in benzene solution) and 1,3-dioxoindan-2-ylidene propanedinitrile (4, in ethanol or acetonitrile solution) act on N-aryl-2,3-dihydro-1H-benz[d,e]isoquinolines 6a-d and N-aryl-6,7-dihydro-5H-dibenz[c,e]azepines 11a-d via hydride abstraction followed by addition of cyanide to the iminium carbon atom forming the corresponding 1- and 5-carbonitriles 9a-d and 13a-d, respectively, in moderate to medium yields.Additionally , the known 1,3-dihydroxy-2H-inden-2-ylidenepropanedinitrile 15 and a novel dispirocyclopropane (17) are formed from 4 in the reaction with 6 in aceton

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13

Khadka, Daulat Bikram, Quynh Manh Le, Su Hui Yang, et al. "Design, synthesis and docking study of 5-amino substituted indeno[1,2-c]isoquinolines as novel topoisomerase I inhibitors." Bioorganic & Medicinal Chemistry 19, no. 6 (2011): 1924–29. http://dx.doi.org/10.1016/j.bmc.2011.01.064.

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14

Pawlas, Jan, Per Vedsø, Palle Jakobsen, Per Olaf Huusfeldt, and Mikael Begtrup. "Synthesis of 1-Hydroxy-Substituted Pyrazolo[3,4-c]- and Pyrazolo[4,3-c]quinolines and -isoquinolines from 4- and 5-Aryl-Substituted 1-Benzyloxypyrazoles." Journal of Organic Chemistry 65, no. 26 (2000): 9001–6. http://dx.doi.org/10.1021/jo000986v.

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15

Kalugin, V. E., and A. M. Shestopalov. "The synthesis of substituted 5-aminopyrido[3′,2′:4,5]thieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives." Russian Chemical Bulletin 67, no. 5 (2018): 902–11. http://dx.doi.org/10.1007/s11172-018-2155-y.

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16

Paronikyan, E. G., Sh Sh Dashyan, A. S. Noravyan, and N. S. Minasyan. "Synthesis of Derivatives of Cyclopenta[4',5']Pyrido-[3',2':4,5]Thieno[3,2-d]Pyrimidines and Pyrimido[5',4':2,3]-Thieno[2,3-c]Isoquinolines." Chemistry of Heterocyclic Compounds 50, no. 8 (2014): 1188–94. http://dx.doi.org/10.1007/s10593-014-1580-6.

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17

Pawlas, Jan, Per Vedsoe, Palle Jakobsen, Per Olaf Huusfeldt, and Mikael Begtrup. "ChemInform Abstract: Synthesis of 1-Hydroxy-Substituted Pyrazolo[3,4-c]- and Pyrazolo[4,3-c]quinolines and -isoquinolines from 4- and 5-Aryl-Substituted 1-Benzyloxypyrazoles." ChemInform 32, no. 19 (2001): no. http://dx.doi.org/10.1002/chin.200119130.

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18

Okuda, Kensuke, Masahiko Yoshida, Takashi Hirota, and Kenji Sasaki. "PolycyclicN-Heterocyclic Compounds 73: Synthesis and Evaluation of 5-Substituted 1,2-Dihydrofuro[2,3-c]isoquinolines as Inducers of Lipoprotein Lipase mRNA Expression." Journal of Heterocyclic Chemistry 50, S1 (2013): E9—E11. http://dx.doi.org/10.1002/jhet.1016.

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19

Paronikyan, E. G., Sh Sh Dashyan, N. S. Minasyan, and G. M. Stepanyan. "Synthesis of 5,8-Diamino-Substituted Pyrano[4″,3″:4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines." Russian Journal of Organic Chemistry 52, no. 4 (2016): 576–81. http://dx.doi.org/10.1134/s1070428016040187.

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20

Okuda, Kensuke, Masahiko Yoshida, Takashi Hirota, and Kenji Sasaki. "Polycyclic N-Heterocyclic Compounds. Part 63: Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce–Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline." CHEMICAL & PHARMACEUTICAL BULLETIN 58, no. 3 (2010): 363–68. http://dx.doi.org/10.1248/cpb.58.363.

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21

Paronikyan, E. G., Sh Sh Dashyan, A. S. Noravyan, et al. "Synthesis and Neurotropic Activity of Amino Derivatives of Cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2-d ]pyrimidines and Pyrimido[4′,5′:4,5]thieno[2,3-c]isoquinolines." Pharmaceutical Chemistry Journal 50, no. 5 (2016): 301–5. http://dx.doi.org/10.1007/s11094-016-1440-z.

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22

Hiremath, S. P., K. Rudresh, and A. R. Saundane. "ChemInform Abstract: Synthesis and Biological Activities of New 5-Hydrazino-10-substituted-7H-indolo[2,3-c]isoquinolines and 1-(10-Substituted-7H-indolo[2,3-c]isoquinolin-5-yl)-3,5-disubstituted Pyrazoles, -3-methyl pyrazol-5-ones, and -3,5-disubstituted." ChemInform 33, no. 19 (2010): no. http://dx.doi.org/10.1002/chin.200219140.

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23

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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24

Felder, C. C., F. E. Albrecht, T. Campbell, G. M. Eisner, and P. A. Jose. "cAMP-independent, G protein-linked inhibition of Na+/H+ exchange in renal brush border by D1 dopamine agonists." American Journal of Physiology-Renal Physiology 264, no. 6 (1993): F1032—F1037. http://dx.doi.org/10.1152/ajprenal.1993.264.6.f1032.

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When D1 dopamine agonists are incubated with renal cortical tissue, Na+/H+ exchange activity is inhibited, presumably due to D1 receptor-mediated stimulation of adenylyl cyclase and subsequent increase in protein kinase A activity. Although the role of adenosine 3',5'-cyclic monophosphate (cAMP) and cAMP-dependent protein kinase in the regulation of Na+/H+ exchange activity is well established, receptors functionally coupled to adenylyl cyclase can regulate Na+/H+ exchange activity independently of changes of cAMP accumulation. The current studies were designed to determine whether D1 agonists

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25

Okuda, Kensuke, Masahiko Yoshida, Takashi Hirota, and Kenji Sasaki. "ChemInform Abstract: Polycyclic N-Heterocyclic Compounds. Part 63. Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce-Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline." ChemInform 41, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.201035164.

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26

Okuda, Kensuke, Masahiko Yoshida, Takashi Hirota та Kenji Sasaki. "Polycyclic N-Heterocyclic Compounds 74: Rearrangement Reaction of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines with α,ω-Dibromoalkanes and Evaluation of Product Bronchodilator Activity". Synthetic Communications 42, № 6 (2011): 865–71. http://dx.doi.org/10.1080/00397911.2010.532899.

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27

Perepichka, Igor, Valery Tolkunov, Oleg Shishkin, Roman Zubatyuk, and Vladimir Dulenko. "Unusual Double ‘O/N to N/O’ Recyclization of 5-Alkyl-7,8-dimethoxy-2-arylbenzo[d]pyrrolo[3,2-b]pyrylium Perchlorates into 5-Alkyl-7,8-dimethoxy-2-arylfuro[2,3-c]isoquinolines." Synlett 2005, no. 06 (2005): 1036–38. http://dx.doi.org/10.1055/s-2005-864806.

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28

Shaker, Raafat M., Kamal U. Sadek, Ebtisam A. Hafez, and Mohamed Abd Elrady. "5-Aminouracil as a Building Block in Heterocyclic Synthesis: Part III. One-pot Synthesis of Novel Pyrimido[5,4-b]quinoline-2,4,9-triones and Pyrimido[5,4-c]isoquinolines." Zeitschrift für Naturforschung B 65, no. 12 (2010): 1485–90. http://dx.doi.org/10.1515/znb-2010-1212.

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An efficient and direct procedure for the synthesis of pyrimido[5,4-b]quinoline-2,4,9-trione and pyrimido[5,4-c]isoquinoline derivatives has been described. The products were characterized by elemental analyses, IR, 1H NMR, 13C NMR and MS spectra.

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29

Okuda, Kensuke, Masahiko Yoshida, Takashi Hirota та Kenji Sasaki. "ChemInform Abstract: Polycyclic N-Heterocyclic Compounds. Part 74. Rearrangement Reaction of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines with α,ω-Dibromoalkanes and Evaluation of Product Bronchodilator Activity." ChemInform 43, № 32 (2012): no. http://dx.doi.org/10.1002/chin.201232159.

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30

Shaker, Raafat M., Kamal U. Sadek, Ebtisam A. Hafez, and Mohamed Abd Elrady. "ChemInform Abstract: 5-Aminouracil as a Building Block in Heterocyclic Synthesis. Part 3. One-Pot Synthesis of Novel Pyrimido[5,4-b]quinoline-2,4,9-triones and Pyrimido[5,4-c]isoquinolines." ChemInform 42, no. 16 (2011): no. http://dx.doi.org/10.1002/chin.201116166.

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31

M. Al-Matar, Hamad, Khaled D. Khalil, and Mohamed H. Elnagdi. "Alkylheteroaromatic-carbonitriles as Building Blocks in Heterocyclic Synthesis: Synthesis of Ethyl 1-Substituted 5-Cyano-4-methyl-6-oxopyridine-3-carboxylates; Versatile Precursors for Polyfunctionally Substituted Isoquinolines and Pyrido[3,4-c]pyridine." HETEROCYCLES 78, no. 8 (2009): 2067. http://dx.doi.org/10.3987/com-09-11685.

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32

Okuda, Kensuke, Hiroshi Deguchi, Setsuo Kashino, Takashi Hirota, and Kenji Sasaki. "Polycyclic N-Heterocyclic Compounds. Part 64: Synthesis of 5-Amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and Related Compounds. Evaluation of Their Bronchodilator Activity and Effects on Lipoprotein Lipase mRNA Expression." CHEMICAL & PHARMACEUTICAL BULLETIN 58, no. 5 (2010): 685–89. http://dx.doi.org/10.1248/cpb.58.685.

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33

Okuda, Kensuke, Hiroshi Deguchi, Setsuo Kashino, Takashi Hirota, and Kenji Sasaki. "ChemInform Abstract: Polycyclic N-Heterocyclic Compounds. Part 64. Synthesis of 5-Amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and Related Compounds. Evaluation of Their Bronchodilator Activity and Effects on Lipoprotein Lipase mRNA Expression." ChemInform 41, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.201045151.

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34

Bates, MRM, LW Deady, and MF Mackay. "A New Synthesis of Pyrazino[2,3-c]isoquinolines." Australian Journal of Chemistry 43, no. 1 (1990): 179. http://dx.doi.org/10.1071/ch9900179.

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A convenient synthesis of 1-(p-chlorophenoxy )isoquinoline-3,4-diame is described. Condensation with ethyl pyruvate gave entry to the tricyclic title system, and some further nucleophilic displacement reactions of substituent groups are described. The direction of ring closure in the tricycle formation was proved by determining the crystal structure of one of the derivatives; rhombohedral crystals of (3b) belong to the space group R3 with a 21.822(5)Ǻ, α 116.81(2)° and Z 12. Full-matrix refinement using 3093 reflections converged at R 0.085.

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35

Deady, LW, and NH Quazi. "Chemistry of Some [1,2,5]Oxadiazolo[3,4-c]isoquinolines and N-Oxides." Australian Journal of Chemistry 46, no. 3 (1993): 411. http://dx.doi.org/10.1071/ch9930411.

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The reaction of some 4-nitroisoquinolin-3-amines with iodosobenzene diacetate [ PhI ( OAc )2] is a convenient preparation of the title compound N-oxides. Attempts to convert these into quinoxaline N,N′-dioxides were not successful, but reactions of some 5-substituents are described, along with deoxygenation to the corresponding furazan derivatives.

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36

Cheng, Jiang, Rui Yang, Xiaopeng Wu, Song Sun та Jin-Tao Yu. "Rhodium-Catalyzed Annulation of 2-Arylimidazoles and α-Aroyl Sulfoxonium Ylides toward 5-Arylimidazo[2,1-a]isoquinolines". Synthesis 50, № 17 (2018): 3487–92. http://dx.doi.org/10.1055/s-0037-1610124.

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A Rh-catalyzed annulation between 2-aryl-1H-benzo[d]imidazoles and α-aroyl sulfoxonium ylides was developed, affording a series of benzimidazo[2,1-a]isoquinolines in moderate to excellent yields. This procedure proceeded with the sequential ortho-C–H functionalization and cyclization, representing a facile and straightforward pathway to access such frameworks.

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37

Manivel, Pitchai, Kamalakannan Prabakaran, Upasana Banerjee, Fazlur-Rahman Nawaz Khan, Euh Duck Jeong, and Eun Hyuk Chung. "Organoiodine(iii) mediated intramolecular oxidative cyclization of 1-(3-arylisoquinolin-1-yl)-2-(arylmethylene)hydrazines to 5-aryl-3-(aryl)-[1,2,4]triazolo[3,4-a] isoquinolines." RSC Advances 5, no. 5 (2015): 3781–85. http://dx.doi.org/10.1039/c4ra12381f.

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Intramolecular C–N bond formation is achieved through oxidative cyclization of 1-(3-arylisoquinolin-1-yl)-2-(arylmethylene)hydrazines, 3, in the presence of hypervalent iodine oxidant and dichloromethane at ambient temperature.

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38

Prabakaran, Kamalakannan, Fazlur-Rahman Khan, Jong Jin, Euh Jeong, and Pitchai Manivel. "Facile synthesis of 3-aryl-1-((4-aryl-1,2,3-selenadiazol-5-yl)sulfanyl)isoquinolines." Chemical Papers 65, no. 6 (2011). http://dx.doi.org/10.2478/s11696-011-0074-6.

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AbstractA new series of 1,2,3-selenadiazoles containing an aryl or a 3-arylisoquinoline sulfanyl moiety at carbons 4 and 5, respectively, was prepared by cyclization of the respective semicarbazones in the presence of selenium(II) oxide and tetrahydrofuran at 70–75°C. Semicarbazones required for the reaction were obtained from 2-((3-arylisoquinolin-1-yl)sulfanyl)-1-phenylethanones, I, by a reaction with semicarbazide hydrochloride in ethanol/water mixture and potassium acetate base.

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