PEG-SO3H as a catalyst in aqueous media: A simple, proficient and green approach for the synthesis of quinoline derivatives

Abstract

A convenient and efficient method was developed for the synthesis of quinolines, an important class of potentially bioactive compounds. The quinoline derivatives were prepared in water, an excellent solvent in terms of environmental impact and with reduced waste production. PEG-SO 3 H effectively catalysed the one-pot synthesis of quinolines by the condensation of o-aminoaryl ketones and carbonyl compound with high yields (75-95%). The compounds were isolated by simple filtration in a high purity form.

Sulfonated polyethylene glycol (PEG-OSO3H) as a polymer supported biodegradable and recyclable catalyst in green organic synthesis: recent advances

“…In order to recover the catalyst, H 2 O was evaporated from the ltrate under reduced pressure, giving a mixture of PEG-OSO 3 H with PEG-400. 34 The compounds were isolated by simple ltration in a high purity form. PEG-OSO 3 H showed better reactivity towards this synthesis in terms of reaction times and product yields compared to other catalysts such as CeCl 3 $7H 2 -O, 113 proline, 114,115 Bronsted ionic liquids, 116,117 Bi(OTf) 3 , 118 SmI 3 , 119 Zn(OTf) 2 (ref.…”

“…29 The high reactivity, lack of diffusion phenomena, analytical simplicity and solubility prole of polyethylene glycols (PEGs with MW >2000 Da) are mostly soluble in polar solvents and insoluble in a few non-polar solvents have established them as good catalysts in homogeneous solid supported catalysis. The present article is intended to review briey in recent research progress concerning the synthesis of different organic compounds catalyzed by PEG-OSO 3 H. 34 At 0 C, chlorosulfonic acid (10 mmol) was added to a solution of PEG-6000 (1 mmol) in dichloromethane (10 mL), and the resulting solution was stirred at room temperature overnight. [31][32][33] Among them PEG-OSO 3 H is a good example of solid supported organic acid catalyst that is functionalized with mild acidity, non-volatility and non-corrosiveness and also recognized as a good surfactant.…”

Catalytic activity of reusable nickel oxide nanoparticles in the synthesis of spirooxindoles

“…16,17 Due to the pharmacological properties of oxindoles, development of synthetic methods enabling easy access to these compounds are desirable. In continuation of our work on the synthesis of biologically important compounds using simple, efficient and nontoxic catalysts, [18][19][20][21][22] in this paper we report synthesis of spirocyclic (5,6,7,8-tetrahydro-4H-chromene)-4,3 0oxindole and dihydro[pyrano [3,2-c]quinoline]-4,3-indoline derivatives by the coupling of malononitrile, 1,3-dicarbonyl/ 4-hydroxycoumarine and isatin derivatives in the presence of nano-NiO as an inexpensive and efficient catalyst in aqueous medium (Scheme 1).…”

Nickel oxide nanoparticles: a green and recyclable catalytic system for the synthesis of diindolyloxindole derivatives in aqueous medium

“…[8][9][10][11][12][13] Because of the pharmacological properties of oxindoles, the development of synthetic methods enabling easy access to these compounds is desirable. In continuation of our work on the synthesis of biologically important compounds using simple, efficient and nontoxic catalysts, [14][15][16][17] in this paper we report the synthesis of diindolyloxindole derivatives by the coupling of indole and isatin derivatives in the presence of nano-NiO, an inexpensive and green catalyst in aqueous medium.…”