Login Register Cart 0
Generic placeholder image

Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

One-pot Multicomponent Reaction: An Efficient Synthesis of 4-(Het)Aryl-substituted Pyrazolo-quinolinones

Author(s): Hüseyin Kerim Beker* and Şeniz Kaban

Volume 21, Issue 3, 2024

Published on: 04 October, 2023

Page: [292 - 297] Pages: 6

DOI: 10.2174/1570179421666230821102745

Price: $65

Abstract

Introduction: Pyrazolo-quinolinones (PQs) are a versatile class of Organic chemistry and it was found that they have very advanced functionally promising as selective compounds due to their scaffold and demonstrated low toxicity and considerable clinical promise. Moreover, these compounds have an important role in different applications such as analytical reagents, technical, pharmaceutical development, and biological markers. So, we aimed to synthesize and characterize new 4-(Het)aryl-substituted Pyrazole-quinolinones.

Methods: Synthesis of One-Pot Multicomponent Reaction was carried out with the reaction of 5- amino-3-methyl-1H-pyrazole 1a, and 5-amino-3-phenyl-1H-pyrazole 1b and dimedone 2 with some (het)aryl aldehydes 3 using ethanol. Characterizations such as the linear structures and the regiospecificity of the reactions were determined by using NMR, GC-MS, IR, and UV measurements.

Results and Conclusion: This research will be very useful for all methods and procedures using multi one-point reactions which are very popular in the synthesis of heterocyclic systems for pyrazole- quinoline skeleton synthesis.

Keywords: Regiospecific pyrazole cyclo-condensation, (het)aryl aldehyde, multicomponent reaction, pyrazolo[3, 4- b]quinoline, organic chemistry, heterocyclic compound.

« Previous Next »
[1]
Thomas, R.; Gilchrist, L. Heterocyclic Chemistry, 3rd ed; Addison Wesley: Essex, England, 1997, p. 414.
[2]
Shaik, A.; Agarwal, H.K.; Bhakuni, R.; Kirubakaran, S. Novel pyrazolo[4, 3-c]quinolin-3-one derivatives as PDE5A inhibitors. Curr. Top. Med. Chem., 2019, 19(4), 305-315.
[http://dx.doi.org/10.2174/1568026619666190208164402] [PMID: 30747070]
[3]
Gomez, L.; Breitenbucher, J.G. PDE2 inhibition: Potential for the treatment of cognitive disorders. Bioorg. Med. Chem. Lett., 2013, 23(24), 6522-6527.
[http://dx.doi.org/10.1016/j.bmcl.2013.10.014] [PMID: 24189054]
[4]
Martinez, G.P.; Zabaleta, M.E.; Di Giulio, C.; Charris, J.E.; Mijares, M.R. The role of chloroquine and hydroxychloroquine in immune regulation and diseases. Curr. Pharm. Des., 2020, 26(35), 4467-4485.
[http://dx.doi.org/10.2174/1381612826666200707132920] [PMID: 32634079]
[5]
Albino, S.L.; da Silva, J.M.; de C Nobre, M.S.; de M E Silva, Y.M.S.; Santos, M.B.; de Araújo, R.S.A.; do C A de Lima, M.; Schmitt, M.; de Moura, RO Bioprospecting of nitrogenous heterocyclic scaffolds with potential action for neglected parasitosis: A. Curr. Pharm. Des., 2020, 26(33), 4112-4150.
[http://dx.doi.org/10.2174/1381612826666200701160904] [PMID: 32611290]
[6]
Jesu Jaya Sudan, R.; Lesitha Jeeva Kumari, J.; Iniyavan, P.; Sarveswari, S.; Vijayakumar, V. Evaluation of xanthene-appended quinoline hybrids as potential leads against antimalarial drug targets. Mol. Divers., 2022, 18.
[PMID: 35583686]
[7]
Dorababu, A. Recent update on antibacterial and antifungal activity of quinoline scaffolds. Arch. Pharm., 2021, 354(3), 2000232.
[http://dx.doi.org/10.1002/ardp.202000232] [PMID: 33210348]
[8]
Becq, F.; Mettey, Y.; Gray, M.A.; Galietta, L.J.; Dormer, R.L.; Merten, M.; Métayé, T.; Chappe, V.; Marvingt-Mounir, C.; Zegarra-Moran, O.; Tarran, R.; Bulteau, L.; Dérand, R.; Pereira, M.M.; McPherson, M.A.; Rogier, C.; Joffre, M.; Argent, B.E.; Sarrouilhe, D.; Becq, F.; Mettey, Y.; Gray, M.A.; Galietta, L.J.V.; Dormer, R.L.; Merten, M.; Métayé, T.; Chappe, V.; Marvingt-Mounir, C.; Zegarra-Moran, O.; Tarran, R.; Bulteau, L.; Dérand, R.; Pereira, M.M.C.; McPherson, M.A.; Rogier, C.; Joffre, M.; Argent, B.E.; Sarrouilhe, D.; Kammouni, W.; Figarella, C.; Verrier, B.; Gola, M.; Vierfond, J.M. Development of substituted Benzo[c]quinolizinium compounds as novel activators of the cystic fibrosis chloride channel. J. Biol. Chem., 1999, 274(39), 27415-27425.
[http://dx.doi.org/10.1074/jbc.274.39.27415] [PMID: 10488073]
[9]
Martín-Encinas, E.; Rubiales, G.; Knudsen, B.R.; Palacios, F.; Alonso, C. Fused chromeno and quinolino[1,8]naphthyridines: Synthesis and biological evaluation as topoisomerase I inhibitors and antiproliferative agents. Bioorg. Med. Chem., 2021, 40, 116177.
[http://dx.doi.org/10.1016/j.bmc.2021.116177] [PMID: 33962152]
[10]
Kappe, C.O. Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog. Acc. Chem. Res., 2000, 33(12), 879-888.
[http://dx.doi.org/10.1021/ar000048h] [PMID: 11123887]
[11]
Liu, Y.T.; Wong, J.K.; Tao, M.; Osterman, R.; Sannigrahi, M.; Girijavallabhan, V.M.; Saksena, A. Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: Synthesis of novel 3, 4-fused tetrahydropyran and tetrahydrofuran prolines. Tetrahedron lett, 2004, 45(32), 6097-6100.
[12]
Beker, H.K. Master Thesis, Yildiz Technical University, Istanbul, Turkey. 2004. Available from: https://www.mastersportal.com/universities/14525/yildiz-technical-university.html
[13]
Chebanov, V.A.; Saraev, V.E.; Desenko, S.M.; Chernenko, V.N.; Knyazeva, I.V.; Groth, U.; Glasnov, T.N.; Kappe, C.O. Tuning of chemo- and regioselectivities in multicomponent condensations of 5-aminopyrazoles, dimedone, and aldehydes. J. Org. Chem., 2008, 73(13), 5110-5118.
[http://dx.doi.org/10.1021/jo800825c] [PMID: 18512991]
[14]
Chebanov, V.A.; Saraev, V.E.; Desenko, S.M.; Chernenko, V.N.; Shishkina, S.V.; Chebanov, V.A.; Saraev, V.E.; Desenko, S.M.; Chernenko, V.N.; Shishkina, S.V.; Shishkin, O.V.; Kobzar, K.M.; Kappe, C.O. One-pot, multicomponent route to pyrazoloquinolizinones. Org. Lett., 2007, 9(9), 1691-1694.
[http://dx.doi.org/10.1021/ol070411l] [PMID: 17385876]
[15]
Zhu, J.; Bienaymé, H.; Wiley, V.C.H. Multicomponent Reactions; Weinheim, Germany, 2005.
[http://dx.doi.org/10.1002/3527605118]

Rights & Permissions Print Cite
Article Metrics
10
1
© 2024 Bentham Science Publishers | Privacy Policy