Generic placeholder image

Current Organic Chemistry

Author(s): Rita M. Borik, Mohamed S. Mostafa, Mohamed S. Behalo and Rizk E. Khidre*

DOI: 10.2174/0113852728285959240108060645

DownloadDownload PDF Flyer Cite As
Recent Progress in the Synthetic Methods of Pyrazoloquinoline Derivatives

Page: [117 - 133] Pages: 17

  • * (Excluding Mailing and Handling)

Explore Articles
About Journal
For Authors
For Editors
For Reviewers

Abstract

The focus of this review is on the synthetic routes available for different types of pyrazoloquinoline derivatives. There are three types of synthetic methods: i) from pyrazole derivatives; ii) from quinoline derivatives; and iii) miscellaneous methods. The position of the linkage between pyrazole and quinoline rings determines the seven isomers of pyrazoloquinolines. The purpose of this review is to provide a guide for both synthetic and medicinal chemists to discover and design new pyrazoloquinolines for medical purposes.

Keywords: Synthesis methods, heterocycles, pyrazoloquinoline, pyrazole, quinolines, pharmacological activities.

Graphical Abstract

[1]
Joule, J.A.; Mills, K. Heterocyclic Chemistry, 5th ed; Wiley-Blackwell: Oxford, 2010.
[2]
Katritzky, A.R.; Ramsden, C.A.; Scriven, E.F.V. Comprehensive Heterocyclic Chemistry III; Taylor, R.J.K., Ed.; Elsevier: Oxford, 2008.
[3]
Orru, R.V.A. Synthesis of Heterocycles via Multicomponent Reactions I; Ruijter, E., Ed.; Springer: Berlin, 2010.
[http://dx.doi.org/10.1007/978-3-642-12675-8]
[4]
Eycken, E. Microwave-Assisted Synthesis of Heterocycles; Kappe, C.O., Ed.; Springer: Berlin, 2006.
[http://dx.doi.org/10.1007/11497363]
[5]
Mekheimer, R.A.; Ahmed, E.A.; Sadek, K.U. Recent developments in the chemistry of pyrazolo[4,3-c]quinolines. Tetrahedron, 2012, 68(6), 1637-1667.
[http://dx.doi.org/10.1016/j.tet.2011.10.088]
[6]
Sabatini, S.; Gosetto, F.; Serritella, S.; Manfroni, G.; Tabarrini, O.; Iraci, N.; Brincat, J.P.; Carosati, E.; Villarini, M.; Kaatz, G.W.; Cecchetti, V. Pyrazolo[4,3-c][1,2]benzothiazines 5,5-dioxide: A promising new class of Staphylococcus aureus NorA efflux pump inhibitors. J. Med. Chem., 2012, 55(7), 3568-3572.
[http://dx.doi.org/10.1021/jm201446h] [PMID: 22432682]
[7]
Baraldi, P.G.; Tabrizi, M.A.; Preti, D.; Bovero, A.; Fruttarolo, F.; Romagnoli, R.; Zaid, N.A.; Moorman, A.R.; Varani, K.; Borea, P.A. New 2-arylpyrazolo[4,3-c]quinoline derivatives as potent and selective human A3 adenosine receptor antagonists. J. Med. Chem., 2005, 48(15), 5001-5008.
[http://dx.doi.org/10.1021/jm050125k] [PMID: 16033279]
[8]
Carotti, A.; Altomare, C.; Savini, L.; Chiasserini, L.; Pellerano, C.; Mascia, M.P.; Maciocco, E.; Busonero, F.; Mameli, M.; Biggio, G.; Sanna, E. High affinity central benzodiazepine receptor ligands. Part 3: Insights into the pharmacophore and pattern recognition study of intrinsic activities of pyrazolo[4,3-c]quinolin-3-ones. Bioorg. Med. Chem., 2003, 11(23), 5259-5272.
[http://dx.doi.org/10.1016/S0968-0896(03)00527-3] [PMID: 14604690]
[9]
Karthikeyan, C.; Amawi, H.; Viana, A.G.; Sanglard, L.; Hussein, N.; Saddler, M.; Ashby, C.R., Jr; Moorthy, N.S.H.N.; Trivedi, P.; Tiwari, A.K. lH-Pyrazolo[3,4-b]quinolin-3-amine derivatives inhibit growth of colon cancer cells via apoptosis and sub G1 cell cycle arrest. Bioorg. Med. Chem. Lett., 2018, 28(13), 2244-2249.
[http://dx.doi.org/10.1016/j.bmcl.2018.05.045] [PMID: 29853331]
[10]
Baruah, B.; Dasu, K.; Vaitilingam, B.; Vanguri, A.; Rao Casturi, S.; Rao Yeleswarapu, K. 1,2-Diaryl-1-ethanone and pyrazolo[4,3-c]quinoline-4-one as novel selective cyclooxygenase-2 inhibitors. Bioorg. Med. Chem. Lett., 2004, 14(2), 445-448.
[http://dx.doi.org/10.1016/j.bmcl.2003.10.052] [PMID: 14698178]
[11]
Chudasama, D.D.; Patel, M.S.; Parekh, J.N.; Patel, H.C.; Rajput, C.V.; Chikhaliya, N.P.; Ram, K.R. Ultrasound-promoted convenient and ionic liquid [BMIM]BF4 assisted green synthesis of diversely functionalized pyrazolo quinoline core via one-pot multicomponent reaction, DFT study and pharmacological evaluation. Mol. Divers., 2023, 27(3), 1409-1425.
[http://dx.doi.org/10.1007/s11030-022-10498-2] [PMID: 35915391]
[12]
Gaurav, A.; Gautam, V.; Singh, R. An overview on synthetic methodologies and biological activities of pyrazoloquinolines. Mini Rev. Med. Chem., 2010, 10(13), 1194-1210.
[http://dx.doi.org/10.2174/13895575110091194] [PMID: 20854254]
[13]
Tomassoli, I.; Herlem, G.; Picaud, F.; Benchekroun, M.; Bautista-Aguilera, O.M.; Luzet, V.; Jimeno, M-L.; Gharbi, T.; Refouvelet, B.; Ismaili, L. Synthesis, regioselectivity, and DFT analysis of new antioxidant pyrazolo[4,3-c]quinoline-3,4-diones. Monatsh. Chem., 2016, 147(6), 1069-1079.
[http://dx.doi.org/10.1007/s00706-016-1660-7]
[14]
He, Z.; Milburn, G.H.W.; Baldwin, K.J.; Smith, D.A.; Danel, A.; Tomasik, P. The efficient blue photoluminescence of pyrazolo-[3,4-b]-quinoline derivatives and the energy transfer in polymer matrices. J. Lumin., 2000, 86(1), 1-14.
[http://dx.doi.org/10.1016/S0022-2313(99)00203-3]
[15]
He, Z.; Milburn, G.H.W.; Danel, A.; Puchala, A.; Tomasik, P.; Rasala, D. Blue electroluminescence of novel pyrazoloquinoline and bispyrazolopyridine derivatives in doped polymer matrices. J. Mater. Chem., 1997, 7(12), 2323-2325.
[http://dx.doi.org/10.1039/a706561b]
[16]
Danel, A.; He, Z.; Milburn, G.H.W.; Tomasik, P. Electroluminescence from novel pyrazole-based polymer systems. J. Mater. Chem., 1999, 9(2), 339-342.
[http://dx.doi.org/10.1039/a808784i]
[17]
Elmansy, M.F.; Borik, R.M.; Khidre, R.E. Synthetic approaches towards taxol; from Holton to Chida. Curr. Org. Chem., 2023, 27(5), 444-459.
[http://dx.doi.org/10.2174/1385272827666230512114730]
[18]
Khidre, R.E.; Mostafa, M.S.; Mukhrish, Y.E.; Salem, M.A.; Behalo, M.S. Synthetic methods of 1h-pyrazolo[1,2-b]phthalazine derivatives. Curr. Org. Chem., 2023, 26(22), 2055-2069.
[http://dx.doi.org/10.2174/1385272827666230124145625]
[19]
Khidre, R.E.; Radini, I.M.A.; Ameen, T.A.; Abdelgawad, A.A.M.; Triazoloquinolines, I. Synthetic methods and pharmacological properties of [1,2,3] triazoloquinoline derivatives. Curr. Org. Chem., 2021, 25(8), 876-893.
[http://dx.doi.org/10.2174/1385272825666210202122645]
[20]
Khidre, R.E.; Ameen, T.A.; Salem, M.A.I. Tetrazoloquinolines: Synthesis, reactions, and applications. Curr. Org. Chem., 2020, 24(4), 439-464.
[http://dx.doi.org/10.2174/1385272824666200217095341]
[21]
Khidre, R.E.; Radini, I.A.M.; Ibrahim, D.A. Synthetic approaches of pyrazolyl quinolines. Mini Rev. Org. Chem., 2019, 16(4), 353-360.
[http://dx.doi.org/10.2174/1570193X15666180419142511]
[22]
Khidre, R.E.; Salem, M.A.; Ameen, T.A.; Abdelgawad, A.A.M.; Triazoloquinolines, I.I.; Triazoloquinolines, II Synthesis, reactions, and pharmacological properties of [1,2,4]triazoloquinoline and 1,2,4-triazoloisoquinoline derivatives. Polycycl. Aromat. Compd., 2023, 43(1), 13-53.
[http://dx.doi.org/10.1080/10406638.2021.2008457]
[23]
Khidre, R.E.; Radini, I.A.M.; Mostafa, M.S.; Ameen, T.A. Synthetic applications of 2-diazo-1,3-indanedione. Indian J. Heterocycl. Chem., 2019, 29, 167-179.
[24]
Guo, Y.Q.; Wu, Y.; Wang, R.; Song, H.; Liu, Y.; Wang, Q. Photoredox/hydrogen atom transfer cocatalyzed C-H difluoroallylation of amides, ethers, and alkyl aldehydes. Org. Lett., 2021, 23(6), 2353-2358.
[http://dx.doi.org/10.1021/acs.orglett.1c00546] [PMID: 33691413]
[25]
Faisca Phillips, A.M.; Pombeiro, A.J.L. Recent developments in transition metal‐catalyzed cross‐dehydrogenative coupling reactions of ethers and thioethers. ChemCatChem, 2018, 10(16), 3354-3383.
[http://dx.doi.org/10.1002/cctc.201800582]
[26]
Mane, K.D.; Kamble, R.B.; Suryavanshi, G. A visible light mediated, metal and oxidant free highly efficient cross dehydrogenative coupling (CDC) reaction between quinoxalin-2(1H)-ones and ethers. New J. Chem., 2019, 43(19), 7403-7408.
[http://dx.doi.org/10.1039/C9NJ00075E]
[27]
Zhou, L.; Tang, S.; Qi, X.; Lin, C.; Liu, K.; Liu, C.; Lan, Y.; Lei, A. Transition-metal-assisted radical/radical cross-coupling: A new strategy to the oxidative C(sp3)-H/N-H cross-coupling. Org. Lett., 2014, 16(12), 3404-3407.
[http://dx.doi.org/10.1021/ol501485f] [PMID: 24921665]
[28]
Singh, M.; Yadav, L.D.S.; Singh, R.K.P. Direct radical sulfonylation at α-C(sp3)-H of THF with sodium sulfinates in aqueous medium. Tetrahedron Lett., 2019, 60(11), 810-813.
[http://dx.doi.org/10.1016/j.tetlet.2019.02.021]
[29]
Barve, B.D.; Wu, Y.C.; El-Shazly, M.; Korinek, M.; Cheng, Y.B.; Wang, J.J.; Chang, F.R. Copper-catalyzed selective C-O bond formation by oxidative α-C(sp3)_H/O_H coupling between ethers and salicylaldehydes. Tetrahedron, 2015, 71(15), 2290-2297.
[http://dx.doi.org/10.1016/j.tet.2015.02.035]
[30]
Mu, Y.; Jiang, R.; Hong, Y.; Hou, J.; Yang, Z.; Tang, D. Acid-catalyzed synthesis of pyrazolo[4,3-c]quinolines from (1H-pyrazol-5-yl)anilines and ethers via the cleavage of C–O bond. Tetrahedron, 2022, 125, 133040.
[http://dx.doi.org/10.1016/j.tet.2022.133040]
[31]
Xie, C.; Feng, L.; Li, W.; Ma, X.; Ma, X.; Liu, Y.; Ma, C. Efficient synthesis of pyrrolo[1,2-a]quinoxalines catalyzed by a Brønsted acid through cleavage of C–C bonds. Org. Biomol. Chem., 2016, 14(36), 8529-8535.
[http://dx.doi.org/10.1039/C6OB01401A] [PMID: 27541576]
[32]
Mayo, M.S.; Yu, X.; Zhou, X.; Feng, X.; Yamamoto, Y.; Bao, M. Convenient synthesis of benzothiazoles and benzimidazoles through Brønsted acid catalyzed cyclization of 2-amino thiophenols/anilines with β-diketones. Org. Lett., 2014, 16(3), 764-767.
[http://dx.doi.org/10.1021/ol403475v] [PMID: 24410080]
[33]
Chakraborty, A.; Majumdar, S.; Maiti, D.K. Selective exploitation of acetoacetate carbonyl groups using imidazolium based ionic liquids: synthesis of 3-oxo-amides and substituted benzimidazoles. Tetrahedron Lett., 2016, 57(30), 3298-3302.
[http://dx.doi.org/10.1016/j.tetlet.2016.06.048]
[34]
Mayo, M.S.; Yu, X.; Zhou, X.; Feng, X.; Yamamoto, Y.; Bao, M. Synthesis of benzoxazoles from 2-aminophenols and β-diketones using a combined catalyst of Brønsted acid and copper iodide. J. Org. Chem., 2014, 79(13), 6310-6314.
[http://dx.doi.org/10.1021/jo500604x] [PMID: 24893749]
[35]
Li, Z.; Dong, J.; Chen, X.; Li, Q.; Zhou, Y.; Yin, S.F. Metal-and oxidant-free synthesis of quinazolinones from β-ketoesters with o-aminobenzamides via phosphorous acid-catalyzed cyclocondensation and selective C–C bond cleavage. J. Org. Chem., 2015, 80(19), 9392-9400.
[http://dx.doi.org/10.1021/acs.joc.5b00937] [PMID: 26339716]
[36]
Nan, J.; Chen, P.; Zhang, Y.; Yin, Y.; Wang, B.; Ma, Y. Metal-free synthesis of 2-substituted quinolines via high chemoselective domino condensation/aza-prins cyclization/retro-aldol between 2-alkenylanilines with β-ketoesters. J. Org. Chem., 2020, 85(21), 14042-14054.
[http://dx.doi.org/10.1021/acs.joc.0c02063] [PMID: 33108195]
[37]
Jiang, R.; Mu, Y.; Zhang, W.; Hong, Y.; Iqbal, Z.; Hou, J.; Yang, Z.; Tang, D. Acid-promoted synthesis of pyrazolo[4,3-c]quinoline derivatives by employing pyrazole-arylamines and β-keto esters via cleavage of C–C bonds. Synth. Commun., 2022, 52(18), 1796-1804.
[http://dx.doi.org/10.1080/00397911.2022.2114372]
[38]
Mu, Y.; Iqbal, Z.; Jiang, R.; Hou, J.; Yang, Z.; Li, H.; Tang, D. Synthesis of fused pyrazolo[4,3‐c]quinolines through KI‐promoted cyclization of pyrazole‐arylamines and benzyl bromide. ChemistrySelect, 2022, 7(10), e202104337.
[http://dx.doi.org/10.1002/slct.202104337]
[39]
Tang, D.; Mu, Y.; Iqbal, Z.; He, L.; Jiang, R.; Hou, J.; Yang, Z.; Yang, M. Construction of substituted pyrazolo[4,3‐c]quinolines via [5+1] cyclization of pyrazole‐arylamines with alcohols/amines in one pot. J. Heterocycl. Chem., 2022, 59(5), 952-957.
[http://dx.doi.org/10.1002/jhet.4420]
[40]
Chaudhary, C.L.; Ko, S.; Lee, C.; Kim, Y.; Jung, C.; Hyun, S.; Kwon, Y.; Kang, J.S.; Jung, J.K.; Lee, H. Design, synthesis, and cytotoxicity and topoisomerase I/IIα inhibition activity of pyrazolo[4,3-f]quinoline derivatives. Pharmaceuticals, 2022, 15(4), 399.
[http://dx.doi.org/10.3390/ph15040399] [PMID: 35455396]
[41]
Pokladko-Kowar, M.; Gondek, E.; Danel, A.; Uchacz, T.; Szlachcic, P.; Wojtasik, K.; Karasiński, P. Trifluoromethyl substituted derivatives of pyrazoles as materials for photovoltaic and electroluminescent applications. Crystals, 2022, 12(3), 434.
[http://dx.doi.org/10.3390/cryst12030434]
[42]
Grabka, D.; Kolbus, A.; Danel, A.; Kucharek, M.; Szary, K. Stationary and time-resolved spectra analysis of pyrazoloquinoline derivatives with pyridyl moiety. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2018, 193, 492-498.
[http://dx.doi.org/10.1016/j.saa.2017.12.066] [PMID: 29291578]
[43]
Uchacz, T.; Szlachcic, P.; Danel, A.; Kukułka, M.; Srebro-Hooper, M.; Stopa, G.; Stadnicka, K.M. Photophysical properties of 1-pyridine-3-phenylpyrazoloquinoline and molecular logic gate implementation. Dyes Pigments, 2019, 166, 490-501.
[http://dx.doi.org/10.1016/j.dyepig.2019.03.031]
[44]
Teleb, M.A.M.; Hassaneen, H.M.; Abdelhamid, I.A.; Saleh, F.M. 5-Aminopyrazole-4-carbonitriles as precursors to novel 4-aminotetrahydropyrazolo[3,4-b]quinolin-5-ones and N-(4-cyanopyrazol-5-yl)pyridine-3-carbonitrile. Synth. Commun., 2021, 51(15), 2357-2364.
[http://dx.doi.org/10.1080/00397911.2021.1936059]
[45]
Chatterjee, T.; Lee, D.S.; Cho, E.J. Extended study of visible-light-induced photocatalytic [4 + 2] benzannulation: Synthesis of polycyclic (hetero)aromatics. J. Org. Chem., 2017, 82(8), 4369-4378.
[http://dx.doi.org/10.1021/acs.joc.7b00413] [PMID: 28332390]
[46]
Liu, T.; Ji, Y.G.; Wu, L. tert-Butyl nitrite-mediated radical cyclization of tetrazole amines and alkynes toward tetrazolo[1,5-a]quinolines. Org. Biomol. Chem., 2019, 17(10), 2619-2623.
[http://dx.doi.org/10.1039/C9OB00169G] [PMID: 30766975]
[47]
Dai, P.; Luo, K.; Yu, X.; Yang, W.C.; Wu, L.; Zhang, W.H. Tert ‐butyl nitrite mediated expeditious methylsulfoxidation of tetrazole‐amines with DMSO: Metal‐free synthesis of antifungal active methylsulfinyl‐1H‐tetrazole derivatives. Adv. Synth. Catal., 2018, 360(3), 468-473.
[http://dx.doi.org/10.1002/adsc.201701364]
[48]
Barak, D.S.; Dahatonde, D.J.; Batra, S. Metal‐ and photoredox‐catalyst free unified approach for the synthesis of azole‐fused quinolines via tert ‐butyl nitrite‐mediated regioselective annulation. Asian J. Org. Chem., 2022, 11(4), e202200057.
[http://dx.doi.org/10.1002/ajoc.202200057]
[49]
Zhang, W.T.; Niu, F.X.; Yue, R.X.; Zhang, Y.; Ma, C.; Sun, J.; Rong, L. A convenient and efficient process for the synthesis of 9‐aryl‐6, 9‐DIHYDRO‐1H‐pyrazolo[3,4‐f] quinoline‐8‐carbonitrile and 1‐aryl‐1,4‐dihydrobenzo [f]quinoline‐2‐carbonitrile derivatives. J. Heterocycl. Chem., 2022, 59(3), 543-554.
[http://dx.doi.org/10.1002/jhet.4400]
[50]
Martín-Acosta, P.; Amesty, Á.; Guerra-Rodríguez, M.; Guerra, B.; Fernández-Pérez, L.; Estévez-Braun, A. Modular synthesis and antiproliferative activity of new dihydro-1H-pyrazolo[1,3-b]pyridine embelin derivatives. Pharmaceuticals, 2021, 14(10), 1026.
[http://dx.doi.org/10.3390/ph14101026] [PMID: 34681250]
[51]
Devi, L.; Nagaraju, K.; Maddila, S.; Jonnalagadda, S.B. A green, efficient protocol for the catalyst-free synthesis of tetrahydro-1H-pyrazolo-[3,4-b]-quinolin-5(4H)-ones supported by ultrasonicirradiation. Chem. Data Collect, 2020, 30, 100566.
[http://dx.doi.org/10.1016/j.cdc.2020.100566]
[52]
Gangu, K.K.; Jvsk, V.K. T, S.G.; Maddila, S.; Jonnalagadda, S.B. Preparation and characterisation of new Ti/Fluorapatite/MWCNTs ternary nanocomposite and its catalytic activity in the synthesis of pyrazolo[3,4-b]quinoline moieties. Mater. Today Commun., 2021, 27, 102206.
[http://dx.doi.org/10.1016/j.mtcomm.2021.102206]
[53]
Yakovenko, G.G.; Yagodkina-Yakovenko, M.S.; Suykov, S.Y.; Vovk, M.V. A Beckmann rearrangement initiated by trifluoromethanesulfonic anhydride in the synthesis of compounds containing a new pyrazolo[3′,4′:5,6]pyrido[3,2-b]azepine heterocyclic system. Chem. Heterocycl. Compd., 2021, 57(2), 199-206.
[http://dx.doi.org/10.1007/s10593-021-02893-8]
[54]
Yadav, P.; Awasthi, A.; Gokulnath, S.; Tiwari, D.K. DMSO as a methine source in TFA-mediated one-pot tandem regioselective synthesis of 3-substituted-1-aryl-1H-pyrazolo-[3,4-b]quinolines from anilines and pyrazolones. J. Org. Chem., 2021, 86(3), 2658-2666.
[http://dx.doi.org/10.1021/acs.joc.0c02696] [PMID: 33423469]
[55]
Lewińska, G.; Khachatryan, K.; Danel, K.S.; Danel, Z.; Sanetra, J.; Marszałek, K.W. Investigations of the optical and thermal properties of the pyrazoloquinoline derivatives and their application for OLED design. Polymers (Basel), 2020, 12(11), 2707.
[http://dx.doi.org/10.3390/polym12112707] [PMID: 33207751]
[56]
Zahedifar, M.; Shojaei, R.; Sheibani, H. Convenient regioselective reaction in presence of H3PW12O40: Synthesis and characterization of pyrazolo[3,4-b]quinoline-3,5-diones. Res. Chem. Intermed., 2018, 44(2), 873-882.
[http://dx.doi.org/10.1007/s11164-017-3141-y]
[57]
Sharma, M.G.; Vala, R.M.; Patel, H.M. Pyridine-2-carboxylic acid as an effectual catalyst for rapid multi-component synthesis of pyrazolo[3,4-b]quinolinones. RSC Advances, 2020, 10(58), 35499-35504.
[http://dx.doi.org/10.1039/D0RA06738E] [PMID: 35515671]
[58]
Zahedifar, M.; Pouramiri, B.; Razavi, R. Triethanolamine lactate-supported nanomagnetic cellulose: A green and efficient catalyst for the synthesis of pyrazolo[3,4-b]quinolines and theoretical study. Res. Chem. Intermed., 2020, 46(5), 2749-2765.
[http://dx.doi.org/10.1007/s11164-020-04117-8]
[59]
Robert Khumalo, M.; Maddila, S.N.; Maddila, S.; Jonnalagadda, S.B. A multicomponent, facile and catalyst-free microwave-assisted protocol for the synthesis of pyrazolo-[3,4-b]-quinolines under green conditions. RSC Advances, 2019, 9(53), 30768-30772.
[http://dx.doi.org/10.1039/C9RA04604F] [PMID: 35529349]
[60]
Khalafy, J.; Majidi, A.F.; Poursattar, M.A.; Sarchami, V. One‐pot, three‐component synthesis of polyfunctionalized benzo[H]pyrazolo[3,4‐B][1,6]naphthyridine and benzo[G]pyrazolo[3,4‐B]quinoline derivatives in the presence of silver nanoparticles (AGNPS). J. Heterocycl. Chem., 2020, 57(11), 3961-3969.
[http://dx.doi.org/10.1002/jhet.4105]
[61]
Marjani, A.P.; Khalafy, J.; Akbarzadeh, S. Synthesis of pyrazolopyridine and pyrazoloquinoline derivatives by one-pot, three-component reactions of arylglyoxals, 3-methyl-1-aryl-1H-pyrazol-5-amines and cyclic 1,3-dicarbonyl compounds in the presence of tetrapropylammonium bromide. Green Process. Synth., 2019, 8(1), 533-541.
[http://dx.doi.org/10.1515/gps-2019-0022]
[62]
Patel, D.M.; Patel, H.J.; Padrón, J.M.; Patel, H.M. A novel substrate directed multicomponent reaction for the syntheses of tetrahydro-spiro[pyrazolo[4,3-f]quinoline]-8,5′-pyrimidines and tetrahydro-pyrazolo[4,3-f]pyrimido[4,5-b]quinolines via selective multiple C–C bond formation under metal-free conditions. RSC Advances, 2020, 10(33), 19600-19609.
[http://dx.doi.org/10.1039/D0RA02990D] [PMID: 35515429]
[63]
Zhang, W.H.; Chen, M.N.; Hao, Y.; Jiang, X.; Zhou, X.L.; Zhang, Z.H. Choline chloride and lactic acid: A natural deep eutectic solvent for one-pot rapid construction of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridines]. J. Mol. Liq., 2019, 278, 124-129.
[http://dx.doi.org/10.1016/j.molliq.2019.01.065]
[64]
Zhu, G.; Gao, L.; Yu, Q.; Qin, Y.; Xi, J.; Rong, L. An efficient synthesis of 1′,7′,8′,9′-tetrahydrospiro[indoline-3,4′-pyrazolo[3,4-b]quinoline]-2,5‘(6’H)-dione derivatives in aqueous medium. J. Heterocycl. Chem., 2018, 55(4), 871-878.
[http://dx.doi.org/10.1002/jhet.3111]
[65]
Manickam, S.; Balijapalli, U.; Sawminathan, S.; Samuelrajamani, P.; Kamaraj, S.; Shanmugam, V.; Ramalingam, S.; Iyer, S.K. One‐pot synthesis and photophysical studies of styryl‐based benzo[f]pyrazolo[3,4‐b]quinoline and Indeno[2,1‐b]pyrazolo[4,3‐e]pyridines. Eur. J. Org. Chem., 2018, 2018(45), 6204-6216.
[http://dx.doi.org/10.1002/ejoc.201801015]
[66]
Manickam, S.; Balijapalli, U.; Sathiyanarayanan, K.I. SnCl2-catalyzed synthesis of dihydro-5H-benzo[f]pyrazolo[3,4-b]quinoline and dihydroindeno[2,1-b]pyrazolo[4,3-e]pyridine with high fluorescence and their photophysical properties. New J. Chem., 2018, 42(2), 860-871.
[http://dx.doi.org/10.1039/C7NJ03654J]
[67]
Polo, E.; Ferrer-Pertuz, K.; Trilleras, J.; Quiroga, J.; Gutiérrez, M. Microwave-assisted one-pot synthesis in water of carbonylpyrazolo[3,4-b]pyridine derivatives catalyzed by InCl3 and sonochemical assisted condensation with aldehydes to obtain new chalcone derivatives containing the pyrazolopyridinic moiety. RSC Advances, 2017, 7(79), 50044-50055.
[http://dx.doi.org/10.1039/C7RA10127A]
[68]
Liu, J.Y.; Chen, J.; Chen, D.M.; Wei, M.; Chen, D.S. An efficient optimization, in situ reduction and cyclization reaction for the synthesis of functionalized pyrazolo[3,4‐f]quinolines derivatives. J. Heterocycl. Chem., 2018, 55(12), 2929-2935.
[http://dx.doi.org/10.1002/jhet.3366]
[69]
Li, H.L.; Chen, J.; Chen, D.S.; Shi, P.; Liu, J.Y. An efficient cascade synthesis of substituted 6,9-dihydro-1H-pyrazolo[3,4-f]quinoline-8-carbonitriles. Heterocycl. Commun., 2018, 24(5), 279-283.
[http://dx.doi.org/10.1515/hc-2018-0131]
[70]
Lewińska, G.; Danel, K.S.; Łukaszewska, I.; Lewiński, G.; Niemiec, W.; Sanetra, J. Ternary organic solar cells doped methoxyphenyl indenopyrazoloquinoline deriva-tives. J. Mater. Sci. Mater. Electron., 2018, 29(20), 17809-17817.
[http://dx.doi.org/10.1007/s10854-018-9890-6]
[71]
Xu, H.; Li, L.; Dai, L.; Mao, K.; Kou, W.; Lin, C.; Rong, L. The efficient in‐situ reduction and cyclization reaction of aromatic aldehyde, 1,3‐cyclopentanedione (tetronic acid), and nitro‐compound under SnCl2•2H2O‐THF medium. Appl. Organomet. Chem., 2018, 32(3), e4194.
[http://dx.doi.org/10.1002/aoc.4194]
[72]
Hegde, H.; Shetty, N.S. Facile one-pot multicomponent synthesis of 1H-pyrazolo[3,4-b]quinolines using L-proline as a catalyst. Chem. Heterocycl. Compd., 2017, 53(8), 883-886.
[http://dx.doi.org/10.1007/s10593-017-2152-3]
[73]
Ghosh, K.; Nishii, Y.; Miura, M. Rhodium-catalyzed annulative coupling using vinylene carbonate as an oxidizing acetylene surrogate. ACS Catal., 2019, 9(12), 11455-11460.
[http://dx.doi.org/10.1021/acscatal.9b04254]
[74]
Ghosh, K.; Nishii, Y.; Miura, M. Oxidative C–H/C–H annulation of imidazopyridines and indazoles through rhodium-catalyzed vinylene transfer. Org. Lett., 2020, 22(9), 3547-3550.
[http://dx.doi.org/10.1021/acs.orglett.0c00975] [PMID: 32282221]
[75]
Mihara, G.; Ghosh, K.; Nishii, Y.; Miura, M. Concise synthesis of isocoumarins through rh-catalyzed direct vinylene annulation: Scope and mechanistic insight. Org. Lett., 2020, 22(14), 5706-5711.
[http://dx.doi.org/10.1021/acs.orglett.0c02112] [PMID: 32638595]
[76]
Li, X.; Huang, T.; Song, Y.; Qi, Y.; Li, L.; Li, Y.; Xiao, Q.; Zhang, Y. Co(III)-catalyzed annulative vinylene transfer via C-H activation: Three-step total synthesis of 8-oxopseudopalmatine and oxopalmatine. Org. Lett., 2020, 22(15), 5925-5930.
[http://dx.doi.org/10.1021/acs.orglett.0c02016] [PMID: 32677835]
[77]
Wang, L.; Shao, Y.; Chen, F.; Qian, P.; Cheng, J. Rhodium-catalyzed directing group-assisted annulation of arene C-H bond with vinylene carbonate toward isocouma-rins. Youji Huaxue, 2022, 42(1), 242-248.
[http://dx.doi.org/10.6023/cjoc202106023]
[78]
Nan, J.; Ma, Q.; Yin, J.; Liang, C.; Tian, L.; Ma, Y. RhIII-Catalyzed formal [5+1]cyclization of 2-pyrrolyl/indolylanilines using vinylene carbonate as a C1 synthon. Org. Chem. Front., 2021, 8(8), 1764-1769.
[http://dx.doi.org/10.1039/D1QO00040C]
[79]
Wang, C.; Fan, X.; Chen, F.; Qian, P.C.; Cheng, J. Vinylene carbonate: Beyond the ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines. Chem. Commun., 2021, 57(32), 3929-3932.
[http://dx.doi.org/10.1039/D1CC00882J] [PMID: 33871531]
[80]
Li, W.; Zhang, M.; Yan, J.; Ni, L.; Cao, H.; Liu, X. Transition metal-and oxidant-free [3+2] cyclization of azomethine imines utilizing vinylene carbonate as dual synthons. Org. Chem. Front., 2022, 9(9), 2529-2533.
[http://dx.doi.org/10.1039/D2QO00308B]
[81]
Evtushok, V.E.; Vorob’ev, A.Y. Synthesis of pyrazolo-and [1,2,4]triazolo-[1,5-a]quinolin-9-ols by cycloaddition to 8-hydroxyquinoline N-imide. Chem. Heterocycl. Compd., 2019, 55(3), 229-234.
[http://dx.doi.org/10.1007/s10593-019-02446-0]
[82]
Meth-Cohn, O.; Narine, B.; Tarnowski, B. A versatile new synthesis of quinolones and related fused pyridines, Part 5. The synthesis of 2-chloroquinolne-3-carbaldehydes. J. Chem. Soc., Perkin Trans. 1, 1981, 1520-1530.
[http://dx.doi.org/10.1039/p19810001520]
[83]
Hayes, R.; Meth-Cohn, O. A versatile new synthesis of quinolones and realted fused pyridines. Part 10. Routes to quinolines with fused azacycles. Tetrahedron Lett., 1982, 23, 1613-1615.
[http://dx.doi.org/10.1016/S0040-4039(00)87172-5]
[84]
Marson, C.M. Reactions of carbonyl compounds with (monohalo) methyleniminium salts (vilsmeier reagents). Tetrahedron, 1992, 48(18), 3659-3726.
[http://dx.doi.org/10.1016/S0040-4020(01)92263-X]
[85]
Munir, R.; Javid, N. Zia-ur-Rehman, M.; Zaheer, M.; Huma, R.; Roohi, A.; Athar, M.M. Synthesis of novel N-acylhydrazones and their C-N/N-N bond conformational characterization by NMR spectroscopy. Molecules, 2021, 26(16), 4908.
[http://dx.doi.org/10.3390/molecules26164908] [PMID: 34443493]
[86]
Chavan, A.S.; Kharat, A.S.; Bhosle, M.R.; Dhumal, S.T.; Mane, R.A. Water mediated and Baker’s yeast accelerated novel synthetic protocols for tetrahydroben-zo[a]xanthene-11-ones and pyrazolo[3,4-b]quinolines. Synth. Commun., 2021, 51, 1-11.
[http://dx.doi.org/10.1080/00397911.2021.1913606]
[87]
Teixeira, F.C.; Lucas, C.; Curto, M.J.M.; André, V.; Duarte, M.T.; Teixeira, A.P.S. Synthesis of novel pyrazolo[3,4-b]quinolinebisphosphonic acids and an unexpected intramolecular cyclization and phosphonylation reaction. Org. Biomol. Chem., 2021, 19(11), 2533-2545.
[http://dx.doi.org/10.1039/D1OB00025J] [PMID: 33666215]
[88]
Alajmi, S.F.; Youssef, T.E. Simple electrochemical synthesis of pyrazolo[4,3-c]quinoline derivatives. Revista de Chimie, 2021, 72(2), 50-58.
[http://dx.doi.org/10.37358/RC.21.2.8419]
[89]
Ackerman, S.E.; Alonso, M.N.; Dornan, D.; Kudirka, R.; Lee, A.; Safina, B.; Zhou, M.; Engleman, E.G. Preparation of immunoconjugate derivatives for use as HER2 modulators. WO Patent 2020190731, 2020.
[90]
Iorio, M.T.; Vogel, F.D.; Koniuszewski, F.; Scholze, P.; Rehman, S.; Simeone, X.; Schnürch, M.; Mihovilovic, M.D.; Ernst, M. GABAA receptor ligands often interact with binding sites in the transmembrane domain and in the extracellular domain-can the promiscuity code be cracked. Int. J. Mol. Sci., 2020, 21(1), 334.
[http://dx.doi.org/10.3390/ijms21010334] [PMID: 31947863]
[91]
Fathy, U.; Azzam, M.A.; Mahdy, F.; El-Maghraby, S.; Allam, R.M. Synthesis and in vitro anticancer activity of some novel tetrahydroquinoline derivatives bearing pyrazol and hydrazide moiety. J. Heterocycl. Chem., 2020, 57(5), 2108-2120.
[http://dx.doi.org/10.1002/jhet.3930]
[92]
Black, S.L.; O’Connor, P.D.; Boyd, M.; Blaser, A.; Kendall, J.D. Synthesis and 1H, 13C and 15N NMR characterisation of substituted Pyrazolo[4,3-c]quinolines and related compounds. Tetrahedron, 2018, 74(22), 2797-2806.
[http://dx.doi.org/10.1016/j.tet.2018.04.061]
[93]
Knutson, D.E.; Kodali, R.; Divović, B.; Treven, M.; Stephen, M.R.; Zahn, N.M.; Dobričić, V.; Huber, A.T.; Meirelles, M.A.; Verma, R.S.; Wimmer, L.; Witzigmann, C.; Arnold, L.A.; Chiou, L.C.; Ernst, M.; Mihovilovic, M.D.; Savić, M.M.; Sieghart, W.; Cook, J.M. Design and synthesis of novel deuterated ligands functionally selective for the γ-aminobutyric acid type A receptor (GABAAR) α6 subtype with improved metabolic stability and enhanced bioavailability. J. Med. Chem., 2018, 61(6), 2422-2446.
[http://dx.doi.org/10.1021/acs.jmedchem.7b01664] [PMID: 29481759]
[94]
Cheng, K.W.; Tseng, C.H.; Yang, C.N.; Tzeng, C.C.; Cheng, T.C.; Leu, Y.L.; Chuang, Y.C.; Wang, J.Y.; Lu, Y.C.; Chen, Y.L.; Cheng, T.L. Specific inhibition of bacterial β-glucuronidase by pyrazolo[4,3-c]quinoline derivatives via a pH-dependent manner to suppress chemotherapy-induced intestinal toxicity. J. Med. Chem., 2017, 60(22), 9222-9238.
[http://dx.doi.org/10.1021/acs.jmedchem.7b00963] [PMID: 29120626]
[95]
G, J.D.; Poornachandra, Y.; Ratnakar, R.K.; Naresh, K.R.; Ravikumar, N.; Krishna, S.D.; Ranjithreddy, P.; Shravan, K.G.; Nanubolu, J.B.; Ganesh, K.C.; Narsaiah, B. Synthesis of novel pyrazolo[3,4-b]quinolinyl acetamide analogs, their evaluation for antimicrobial and anticancer activities, validation by molecular modeling and CoMFA analysis. Eur. J. Med. Chem., 2017, 130, 223-239.
[http://dx.doi.org/10.1016/j.ejmech.2017.02.052] [PMID: 28254697]
[96]
Zhou, Q.; Yu, H.Y.; Zhou, Y.; Wei, J.R.; Wang, L. Cu(II)-Mediated aerobic oxidative synthesis of sulfonated chromeno[4,3-c]pyrazol-4(2H)-ones. Org. Biomol. Chem., 2022, 20(28), 5575-5581.
[http://dx.doi.org/10.1039/D2OB00639A] [PMID: 35792135]
[97]
Zhang, C.; Dong, S.; Zheng, Y.; He, C.; Chen, J.; Zhen, J.; Qiu, L.; Xu, X. Synthesis of spiro-4H-pyrazole-oxindoles and fused 1H-pyrazoles via divergent, thermally induced tandem cyclization/migration of alkyne-tethered diazo compounds. Org. Biomol. Chem., 2018, 16(5), 688-692.
[http://dx.doi.org/10.1039/C7OB02802D] [PMID: 29239450]
[98]
Shahbazi-Alavi, H.; Alemi-Tameh, F.; Safaei-Ghomi, J. Synthesis of spiro-oxindoles catalyzed by nano-Co3S4. Monatsh. Chem., 2018, 149(11), 2031-2036.
[http://dx.doi.org/10.1007/s00706-018-2246-3]
[99]
Alemi, T.F.; Safaei-Ghomi, J. Synthesis of spiro[pyrazoloquinoline-oxindoles] and spiro[chromenopyrazolo-oxindoles] promoted by guanidine-functionalized magnetic Fe3O4 nanoparticles. J. Indian Chem. Soc., 2018, 15(7), 1633-1637.
[http://dx.doi.org/10.1007/s13738-018-1361-8]
[100]
Hosseinjani-Pirdehi, H.; Rad-Moghadam, K.; Youseftabar-Miri, L. A fourcomponent synthesis of novel spiro[pyrazoloquinoline-oxindoles] under solvent-free conditions. Tetrahedron, 2014, 70(9), 1780-1785.
[http://dx.doi.org/10.1016/j.tet.2014.01.025]