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Journal articles on the topic 'Friedländer reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 February 2022

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1

Hsiao, Yi, Nelo R. Rivera, Nobuyoshi Yasuda, David L. Hughes, and Paul J. Reider. "Highly Regioselective Friedländer Reaction." Organic Letters 3, no. 8 (2001): 1101–3. http://dx.doi.org/10.1021/ol006785v.

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2

Hsiao, Yi, Nelo R. Rivera, Nobuyoshi Yasuda, David L. Hughes, and Paul J. Reider. "Highly Regioselective Friedländer Reaction." Organic Letters 4, no. 7 (2002): 1243. http://dx.doi.org/10.1021/ol020048c.

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3

Bekolo, Henri, and Gilbert Kirsch. "Synthesis of substituted 4-azaisoindoles — New tacrine analogues." Canadian Journal of Chemistry 85, no. 1 (2007): 1–6. http://dx.doi.org/10.1139/v06-180.

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The regioselective Friedländer reaction of 3-amino-4-cyanopyrroles with a series of cyclic ketones has enabled the first reported synthesis of substituted 4-azaisoindoles. Structurally, this new class of compounds stands for the first reported 4-azaisoindole tacrine analogues. A reaction mechanism for the formation of the reported 4-azaisoindoles is proposed.Key words: 4-azaisoindoles, tacrine, Friedländer reaction, pyrroles, mechanism.

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4

Gupta, Anoop K., Dinesh De, and Parimal K. Bharadwaj. "A NbO type Cu(ii) metal–organic framework showing efficient catalytic activity in the Friedländer and Henry reactions." Dalton Transactions 46, no. 24 (2017): 7782–90. http://dx.doi.org/10.1039/c7dt01595j.

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5

López-Sanz, Jesús, Elena Pérez-Mayoral, Dana Procházková, Rosa M. Martín-Aranda, and Antonio J. López-Peinado. "Zeolites Promoting Quinoline Synthesis via Friedländer Reaction." Topics in Catalysis 53, no. 19-20 (2010): 1430–37. http://dx.doi.org/10.1007/s11244-010-9603-8.

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6

Lunchev, Andrey V., Vincent C. Hendrata, Aparna Jaggi, et al. "A Friedländer route to 5,7-diazapentacenes." Journal of Materials Chemistry C 6, no. 14 (2018): 3715–21. http://dx.doi.org/10.1039/c7tc05057g.

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7

Garrison, Aaron T., Yasmeen Abouelhassan, Hongfen Yang, Hussain H. Yousaf, Tho J. Nguyen, and Robert W. Huigens III. "Microwave-enhanced Friedländer synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria." MedChemComm 8, no. 4 (2017): 720–24. http://dx.doi.org/10.1039/c6md00381h.

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8

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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9

Wan, Junlin, Hongxin Liu, Yunjun Lan, et al. "Catalytic Asymmetric Synthesis of Atropisomeric Quinolines through the Friedländer Reaction." Synlett 30, no. 19 (2019): 2198–202. http://dx.doi.org/10.1055/s-0039-1690228.

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A phosphoric acid catalyzed atroposelective Friedländer reaction was developed in which acetylacetone and a variety of 2′-substituted 2-aminobenzophenones were successfully employed to give optically active biaryl quinolines in good yields and with high enantioselectivities.

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10

Gao, Wen-Yang, Kunyue Leng, Lindsay Cash, et al. "Investigation of prototypal MOFs consisting of polyhedral cages with accessible Lewis-acid sites for quinoline synthesis." Chemical Communications 51, no. 23 (2015): 4827–29. http://dx.doi.org/10.1039/c4cc09410g.

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11

Long, Yuhua, Haifeng Zhang, and Dingqiao Yang. "Efficient Synthesis of Ferrocenylquinolines via the Friedländer Reaction." Synthetic Communications 43, no. 5 (2012): 619–34. http://dx.doi.org/10.1080/00397911.2010.519090.

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12

Chen, Ying, Jinkun Huang, Tsang-Lin Hwang, et al. "A highly regioselective Friedländer reaction mediated by lanthanum chloride." Tetrahedron Letters 53, no. 26 (2012): 3237–41. http://dx.doi.org/10.1016/j.tetlet.2012.04.038.

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13

Xu, Jingxiu, Qingmao Chen, Zhigao Luo, Xiaodong Tang, and Jinwu Zhao. "N-Heterocyclic carbene copper catalyzed quinoline synthesis from 2-aminobenzyl alcohols and ketones using DMSO as an oxidant at room temperature." RSC Advances 9, no. 49 (2019): 28764–67. http://dx.doi.org/10.1039/c9ra04926f.

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A facile and practical process for the synthesis of quinolines through an N-heterocyclic carbene copper catalyzed indirect Friedländer reaction from 2-aminobenzyl alcohol and aryl ketones using DMSO as an oxidant at room temperature is reported.

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14

Ma, Fei-Ping, Gui-Tian Cheng, Zhi-Guo He, and Zhan-Hui Zhang. "A New and Efficient Procedure for Friedländer Synthesis of Quinolines in Low Melting Tartaric Acid-Urea Mixtures." Australian Journal of Chemistry 65, no. 4 (2012): 409. http://dx.doi.org/10.1071/ch12025.

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A general, efficient and green method for the synthesis of quinoline derivatives via the Friedländer heteroannulation reaction of 2-aminoaryl ketones and α-methylene ketones has been developed, employing low melting mixtures of L-(+)-tartaric acid and urea derivatives as an inexpensive, non-toxic, easily biodegradable reaction medium. The melt acts as both the reaction medium and catalyst, furnishing quinolines in high to excellent yields.

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15

Rozhkova, Yuliya S., Tatyana S. Storozheva, Irina V. Plekhanova, Alexey A. Gorbunov, Andrej A. Smolyak, and Yurii V. Shklyaev. "Synthesis of Aminoalkyl-Functionalized 4-Arylquinolines from 2-(3,4-Dihydroisoquinolin-1-yl)anilines via the Friedländer Reaction." Synthesis 53, no. 01 (2020): 146–60. http://dx.doi.org/10.1055/s-0040-1706424.

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A new approach for the efficient and convenient synthesis of novel aminoalkyl-functionalized 4-arylquinolines via the Friedländer reaction of differently substituted 2-(3,4-dihydroisoquinolin-1-yl)anilines with various α-methylene ketones in acetic acid was developed. The reaction allows easy access to a diversity of 4-arylquinoline derivatives in moderate to excellent yields under mild conditions.

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16

Comesse, Sébastien, and Adam Daïch. "An Unprecedented Straightforward Synthesis of Chiral Pyrrolo[3,4-b]quinolone and Pyrrolo[3,2-b]quinolone Backbones Starting fromtrans-4-Hydroxy-L-proline." Journal of Chemistry 2016 (2016): 1–5. http://dx.doi.org/10.1155/2016/1504682.

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The straightforward synthesis of pyrrolo[3,4-b]quinolone and pyrrolo[3,2-b]quinolone backbones, which can be found in molecules exhibiting anticancer activities, is presented. The key step of the process is an efficient and unprecedented Friedländer condensation between an oxoproline carbamate, obtained in 3 steps and good yield starting from commercially available and relatively cheaptrans-4-hydroxy-L-proline, and various 2-amino-substituted carbonyl derivatives. It was demonstrated that the formation of the two possible regioisomers was fully triggered by both the R substituent onto the 2-am

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17

Jahng, Yurngdong, and Moinul Karim. "Synthesis of 5-azapentacene by Friedländer reaction and its properties." Tetrahedron 72, no. 1 (2016): 199–204. http://dx.doi.org/10.1016/j.tet.2015.11.026.

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18

Yang, Dingqiao, Kailing Jiang, Jingning Li, and Feng Xu. "Synthesis and characterization of quinoline derivatives via the Friedländer reaction." Tetrahedron 63, no. 32 (2007): 7654–58. http://dx.doi.org/10.1016/j.tet.2007.05.037.

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19

Rafiee, Ezzat, Fereshte Khajooei Nejad, and Mohammad Joshaghani. "CsxH3−xPW12O40 heteropoly salts catalyzed quinoline synthesis via Friedländer reaction." Chinese Chemical Letters 22, no. 3 (2011): 288–91. http://dx.doi.org/10.1016/j.cclet.2010.09.036.

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20

Bender, Matthias, and Jens Christoffers. "Investigations into the Regioselectivity of Fischer Indole and Friedländer Quinoline Syntheses with Octahydroisobenzofuran and Octahydroisoindole Derivatives." Zeitschrift für Naturforschung B 66, no. 12 (2011): 1209–18. http://dx.doi.org/10.1515/znb-2011-1203.

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A Fischer indole synthesis with a cis-configurated octahydroisobenzofuran-6-one yielded exclusively a furo[3,4-c]carbazole derivative as the product of a regioselective angular annulation reaction. A Friedländer quinoline synthesis from the same substrate gave a mixture of angular and linear annulation products, i. e. furo[3,4-a]acridine and furo[3,4-b]acridine derivatives. When submitting a mixture of cis- and trans-octahydroisoindole derivatives to Fischer and Friedländer syntheses, the trans-starting material gave regioselectively linear annulation products, i. e. pyrrolo[3,4-b]carbazole an

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21

V. Ryabukhin, Sergey, Andrey S. Plaskon, Vasiliy S. Naumchik, Dmitriy M. Volochnyuk, Sergey E. Pipko, and Andrey A. Tolmachev. "Heterocyclic Ortho-Aminocarbonyl Compounds in the Friedländer Reaction Promoted by Chlorotrimethylsilane." HETEROCYCLES 71, no. 11 (2007): 2397. http://dx.doi.org/10.3987/com-07-11128.

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22

Piao, Ming-Zhu, and Kimiaki Imafuku. "Friedländer reaction of 3-acetyltropolone: Synthesis of 3-(2-quinolyl)tropolones." Journal of Heterocyclic Chemistry 32, no. 4 (1995): 1373–75. http://dx.doi.org/10.1002/jhet.5570320444.

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23

Lemport, Pavel S., Georgy V. Bodrin, Andrey I. Belyakov, Pavel V. Petrovskii, Anna V. Vologzhanina, and Edward E. Nifant’ev. "Friedländer reaction in the synthesis of 2-(phosphoryl)alkyl-substituted 1,6-naphthyridines." Mendeleev Communications 19, no. 6 (2009): 303–5. http://dx.doi.org/10.1016/j.mencom.2009.11.002.

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24

Pérez-Mayoral, Elena, Zuzana Musilová, Barbara Gil, et al. "Synthesis of quinolines via Friedländer reaction catalyzed by CuBTC metal–organic-framework." Dalton Transactions 41, no. 14 (2012): 4036. http://dx.doi.org/10.1039/c2dt11978a.

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25

Kiss, Árpád, Attila Potor, and Zoltán Hell. "Heterogeneous Catalytic Solvent-free Synthesis of Quinoline Derivatives via the Friedländer Reaction." Catalysis Letters 125, no. 3-4 (2008): 250–53. http://dx.doi.org/10.1007/s10562-008-9573-7.

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26

Pérez-Mayoral, Elena, and Jiří Čejka. "[Cu3(BTC)2]: A Metal-Organic Framework Catalyst for the Friedländer Reaction." ChemCatChem 3, no. 1 (2010): 157–59. http://dx.doi.org/10.1002/cctc.201000201.

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27

Li, Yang, and Wentao Gao. "Synthesis of 3-(quinolin-2-yl)- and 3,6-bis(quinolin-2-yl)-9H-carbazoles." Beilstein Journal of Organic Chemistry 6 (October 8, 2010): 966–72. http://dx.doi.org/10.3762/bjoc.6.108.

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A simple and efficient synthesis of novel 3-(quinolin-2-yl)- and 3,6-bis(quinolin-2-yl)-9H-carbazoles, utilizing sodium ethoxide as a catalyst via a Friedländer condensation reaction between 3-acetyl-9-ethyl-9H-carbazole or 3,6-diacetyl-9-ethyl-9H-carbazole and β-aminoaldehydes or β-aminoketones is described. All of the title compounds were obtained in good yields of 52–72% and their structures were confirmed by IR, 1H NMR, MS, and elemental analysis.

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28

Gao, Wentao, Jia Liu, Yun Jiang, and Yang Li. "First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives." Beilstein Journal of Organic Chemistry 7 (February 15, 2011): 210–17. http://dx.doi.org/10.3762/bjoc.7.28.

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A facile and inexpensive synthesis of a series of novel methylenedioxy-bearing 2-(benzofuran-2-yl)-quinoline-3-carboxylic acid derivatives 3a–h via the one-pot reaction of ethyl 2-chloromethyl-6,7-methylenedioxyquinoline-3-carboxylate (5) with various substituted salicylaldehydes 6a–g as well as 2-hydroxy-1-naphthaldehyde (6h) is described. Substrate 5 was synthesized by the Friedländer condensation reaction of 2-amino-4,5-methylenedioxybenzaldehyde (4) with ethyl 4-chloro-3-oxobutanoate using KHSO4 as catalyst under ultrasound irradiation conditions. The targeted compounds 3a–h were obtained

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29

Gao, Wentao, Guihai Lin, Yang Li, Xiyue Tao, Rui Liu, and Lianjie Sun. "An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives." Beilstein Journal of Organic Chemistry 8 (October 30, 2012): 1849–57. http://dx.doi.org/10.3762/bjoc.8.213.

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An efficient access to the tetracyclic-fused quinoline systems, 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives 4a–l, is described, involving the intramolecular Friedel–Crafts acylation reaction of 2-(phenoxymethyl)-4-phenylquinoline-3-carboxylic acid derivatives 3a–l aided by the treatment with PPA (polyphosphoric acid) or Eaton’s reagent. The required starting compound (2) was obtained by Friedländer reaction of 2-aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a–l were pre

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30

Genovese, Salvatore, Francesco Epifano, Maria Carla Marcotullio, Caroline Pelucchini, and Massimo Curini. "An alternative quinoline synthesis by via Friedländer reaction catalyzed by Yb(OTf)3." Tetrahedron Letters 52, no. 27 (2011): 3474–77. http://dx.doi.org/10.1016/j.tetlet.2011.04.109.

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31

Piao, Ming-Zhu, and Kimiaki Imafuku. "Friedländer reaction of 3-acetyltropolones: Synthesis of naphthyridinyl- and allied heterocyclic-substituted tropolones." Journal of Heterocyclic Chemistry 33, no. 2 (1996): 389–98. http://dx.doi.org/10.1002/jhet.5570330230.

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32

Wang, Limin, Qiang Shen, Jianjun Yu, et al. "Synthesis of Quinolines via Friedländer Reaction in Water and under Catalyst-Free Conditions." Synthesis 44, no. 03 (2011): 389–92. http://dx.doi.org/10.1055/s-0031-1289657.

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33

Zhichkin, Pavel, Catherine Beer, W. Rennells, and David Fairfax. "A One-Pot Method for the Synthesis of Naphthyridines via Modified Friedländer Reaction." Synlett 2006, no. 03 (2006): 0379–82. http://dx.doi.org/10.1055/s-2006-926229.

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34

Yang, Dingqiao, Wei Guo, Yuepeng Cai, Lasheng Jiang, Kailing Jiang, and Xiaobing Wu. "Efficient synthesis of novel six-member ring-fused quinoline derivatives via the friedländer reaction." Heteroatom Chemistry 19, no. 3 (2008): 229–33. http://dx.doi.org/10.1002/hc.20356.

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35

Mori, Takahiro, Kimiaki Imafuku, Ming-Zhu Piao, and Kunihide Fujimori. "Synthesis of 1- and 2-(2-quinolyl)azulenes by the friedländer reaction of acetylazulenes." Journal of Heterocyclic Chemistry 33, no. 3 (1996): 841–46. http://dx.doi.org/10.1002/jhet.5570330350.

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36

P., Rahul, Nitha P. R., Vishnu K. Omanakuttan, et al. "Superbase-Mediated Indirect Friedländer Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines." European Journal of Organic Chemistry 2020, no. 20 (2020): 3081–89. http://dx.doi.org/10.1002/ejoc.202000365.

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37

Mutlak A. Hassan, Hani, and Iuliana Denetiu. "A Mild and Efficient Ga(OTf)3-Catalysed Friedländer Reaction for the Synthesis of Quinolines." HETEROCYCLES 98, no. 6 (2019): 838. http://dx.doi.org/10.3987/com-19-14085.

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38

Gavara, Laurent, Thomas Boisse, Jean-Pierre Hénichart, Adam Daïch, Benoît Rigo, and Philippe Gautret. "Toward new camptothecins. Part 6: Synthesis of crucial ketones and their use in Friedländer reaction." Tetrahedron 66, no. 38 (2010): 7544–61. http://dx.doi.org/10.1016/j.tet.2010.07.048.

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39

Nedeltchev, Alexi K., Haesook Han, and Pradip K. Bhowmik. "Photoactive amorphous molecular materials based on quinoline amines and their synthesis by Friedländer condensation reaction." Tetrahedron 66, no. 48 (2010): 9319–26. http://dx.doi.org/10.1016/j.tet.2010.09.108.

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40

Bhowmik, Pradip K., Alexi K. Nedeltchev, Haesook Han, et al. "Photoactive amorphous molecular materials based on bisquinoline diamines and their synthesis by Friedländer condensation reaction." Journal of Photochemistry and Photobiology A: Chemistry 283 (June 2014): 45–55. http://dx.doi.org/10.1016/j.jphotochem.2014.03.021.

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41

Boisse, Thomas, Laurent Gavara, Jean-Pierre Hénichart, Benoît Rigo, and Philippe Gautret. "Toward new camptothecins. Part 5: On the synthesis of precursors for the crucial Friedländer reaction." Tetrahedron 65, no. 12 (2009): 2455–66. http://dx.doi.org/10.1016/j.tet.2009.01.077.

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42

Li, Jia Rong, Li Jun Zhang, Jin Nan Chen, et al. "Synthesis of 2H-3,1-pyrazolo[3,4-e]oxazines via a new conversion of Friedländer reaction." Chinese Chemical Letters 18, no. 6 (2007): 636–38. http://dx.doi.org/10.1016/j.cclet.2007.04.015.

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43

Hong, Wan Pyo, Inji Shin, and Hee Nam Lim. "Recent Advances in One-Pot Modular Synthesis of 2-Quinolones." Molecules 25, no. 22 (2020): 5450. http://dx.doi.org/10.3390/molecules25225450.

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It is known that 2-quinolones are broadly applicable chemical structures in medicinal and agrochemical research as well as various functional materials. A number of current publications about their synthesis and their applications emphasize the importance of these small molecules. The early synthetic chemistry originated from the same principle of the classical Friedländer and Knorr procedures for the preparation of quinolines. The analogous processes were developed by applying new synthetic tools such as novel catalysts, the microwave irradiation method, etc., whereas recent innovations in ne

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44

Li, Jiarong, Lijun Zhang, Daxin Shi, et al. "Investigation of the Reaction of o-Aminonitriles with Ketones: A New Modification of Friedländer Reaction and Structures of Its Products." Synlett 2008, no. 2 (2008): 233–36. http://dx.doi.org/10.1055/s-2007-1000841.

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45

Bodrin, Georgy V., Pavel S. Lemport, Sergey V. Matveev, Pavel V. Petrovskii, and Edward E. Nifant’ev. "The first application of the Friedländer reaction for the synthesis of [1,8]naphthyridine derivatives containing phosphorus." Mendeleev Communications 17, no. 1 (2007): 25–26. http://dx.doi.org/10.1016/j.mencom.2007.01.010.

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46

Mamedov, Vakhid A., Saniya F. Kadyrova, Nataliya A. Zhukova, Venera R. Galimullina, Fedor M. Polyancev, and Shamil K. Latypov. "Friedländer reaction/quinoxalinone–benzimidazole rearrangement sequence: expeditious entry to diverse quinoline derivatives with the benzimidazole moieties." Tetrahedron 70, no. 35 (2014): 5934–46. http://dx.doi.org/10.1016/j.tet.2014.06.007.

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47

Položij, Miroslav, Elena Pérez-Mayoral, Jiři Čejka, Jan Hermann, and Petr Nachtigall. "Theoretical investigation of the Friedländer reaction catalysed by CuBTC: Concerted effect of the adjacent Cu2+ sites." Catalysis Today 204 (April 2013): 101–7. http://dx.doi.org/10.1016/j.cattod.2012.08.025.

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48

Palma, Alirio, Angie Meléndez, Esteban Plata, et al. "Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones." Synthesis 52, no. 12 (2020): 1804–22. http://dx.doi.org/10.1055/s-0039-1707985.

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An alternative and efficient one-step approach to develop small libraries of polysubstituted 4-styrylquinolines/4-styrylquinolin-2-ones and 9-styryldihydroacridin-1-ones is described. According to this approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedländer reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C

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49

Domínguez-Fernández, Fernando, Jesús López-Sanz, Elena Pérez-Mayoral, et al. "Novel Basic Mesoporous Catalysts for the Friedländer Reaction from 2-Aminoaryl Ketones: Quinolin-2(1H)-ones versus Quinolines." ChemCatChem 1, no. 2 (2009): 241–43. http://dx.doi.org/10.1002/cctc.200900097.

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50

Gao, Wentao, Xiuping Cheng, and Yang Li. "Synthesis of Quinoline-Bearing Ferrocene Derivatives via Friedländer Reaction of Acetyl- and 1,1’-Diacetylferrocenes with o-Amino Aryl Aldehydes." HETEROCYCLES 81, no. 8 (2010): 1923. http://dx.doi.org/10.3987/com-10-11980.

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