Eco-Friendly Methodologies for the Synthesis of Quinoline Nucleus

Author(s): Ligia S. da Silveira Pinto, Thatyana R. Alves Vasconcelos, Marcus V.N. de Souza*

Journal Name: Mini-Reviews in Organic Chemistry

Volume 16 , Issue 6 , 2019

Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


The quinoline nucleus is a very important class of heterocyclic aromatic compounds present in several drugs on the market, with synthetic methodologies being necessary to prepare its nucleus and derivatives. Considering that fact, the aim of this review is to describe the development of eco-friendly methodologies for the synthesis of quinoline nucleus and its derivatives in the last five years. Thus, throughout the text are presented varios reagents and catalysts used in the synthesis of quinoline nucleus, the reaction conditions, the advantages of the described methodologies, along with the reaction scheme and some reaction mechanisms.

Keywords: Drugs, green chemistry, quinoline nucleus, antituberculosis drugs, heterocyclic aromatic compounds, Friedländer synthesis.

Marella, A.; Tanwar, O.P.; Saha, R.; Ali, M.R.; Srivastava, S.; Akhter, M.; Shaquiquzzaman, M.; Alam, M.M. Quinoline: A versatile heterocyclic. Saudi Pharm. J., 2013, 21, 1-12.
Bharate, J.B.; Vishwakarma, R.A.; Bharate, S.B. Metal-free domino one-pot protocols for quinoline synthesis. RSC Advances, 2015, 5, 42020-42053.
Barbosa-Lima, G.; Da Silveira Pinto, L.S.; Kaiser, C.R.; Wardell, J.L.; De Freitas, C.S.; Vieira, Y.R.; Marttorelli, A.; Cerbino Neto, J.; Bozza, P.T.; Wardell, S.M.S.V.; de Souza, M.V.N.; Souza, T.M.L. N-(2-(arylmethylimino)ethyl)-7-chloroquinolin-4-amine derivatives, synthesized by thermal and ultrasonic means, are endowed with anti-Zika virus activity. Eur. J. Med. Chem., 2017, 127, 434-441.
Barbosa-Lima, G.; Moraes, A.M.; Araújo, A.D.S.; da Silva, E.T.; de Freitas, C.S.; Vieira, Y.R.; Marttorelli, A.; Neto, J.C.; Bozza, P.T.; de Souza, M.V.N.; Souza, T.M.L. 2,8-bis(trifluoro-methyl) quinoline analogs show improved anti-Zika virus activity, compared to mefloquine. Eur. J. Med. Chem., 2017, 127, 334-340.
Singh, A.; Prakash, V.; Kant, S.; Kumar, R.; Bhatia, A.; Verma, A.K.; Srivastava, A. Bedaquiline: A new hope in treatment of tuberculosis. Int. J. Health Allied Sci., 2016, 5(3), 172-173.
Naidoo, S.; Jeena, V. Synthesis of 2,4-disubstituted quinoline derivatives via a3-coupling: An EcoScale evaluation. Synthesis, 2017, 49, 2621-2631.
Broman, G.I.; Robèrt, K-H. A framework for strategic sustainable development. J. Clean. Prod., 2017, 140, 17-31.
Hejazi, S.Z.; Shojaei, A.F.; Tabatabaeian, K.; Shirini, F. Preparation and characterization of ZrO2-supported Fe3O4-MNPs as an effective and reusable superparamagnetic catalyst for the Friedländer synthesis of quinoline derivatives. J. Serb. Chem. Soc., 2015, 80(8), 971-982.
More, P.A.; Shankarling, G.S. Energy efficient Pfitzinger reaction: A novel strategy using a surfactant catalyst. New J. Chem., 2017, 41, 12380-12383.
Nasseri, M.A.; Zakerinasab, B.; Kamayestani, S. Proficient procedure for preparation of quinoline derivatives catalyzed by NbCl5 in glycerol as green solvent. J. Appl. Chem, 2015.
Ahmed, W.; Zhang, S.; Yu, X.; Yamamoto, Y.; Bao, M. Brønsted acid-catalyzed metal- and solvent-free quinoline synthesis from N-alkyl anilines and alkynes or alkenes. Green Chem., 2018, 20, 261-265.
Yahya, S.; Beheshtiha, S.H.; Majid, M.; Dehghani, M. Sulfamic acid: An efficient and recyclable solid acid catalyst for the synthesis of quinoline-4-carboxylic acid derivatives in water. Mod. Chem. APPL, 2016, 4(4), 1-6.
Shahabi, D.; Tavakol, H. One-pot synthesis of quinoline derivatives using choline chloride/tin (II) chloride deep eutectic solvent as a green catalyst. J. Mol. Liq., 2016, 220, 324-328.
Sapkota, K.; Han, S.S. A novel environmentally sustainable synthesis of Au-Ag@AgCl nanocomposites and their application as an efficient and recyclable catalyst for quinoline synthesis. New J. Chem., 2017, 41, 5395-5402.
Li, A.; Huang, C.; Luo, C-W.; Yi, W-J.; Chao, Z-S. High-efficiency catalytic performance over mesoporous Ni/beta zeolite for the synthesis of quinoline from glycerol and aniline. RSC Advances, 2017, 7, 9551-9561.

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2019
Published on: 26 August, 2019
Page: [602 - 608]
Pages: 7
DOI: 10.2174/1570193X16666181228101137
Price: $65

Article Metrics

PDF: 39