Well-Ordered Mesoporous Silica Nanoparticles as a Recoverable Catalyst for One-Pot Multicomponent Synthesis of 4H-Chromene Derivatives

Abstract

A simple, efficient and environmentally benign protocol for the synthesis of 4H-chromene derivatives was developed using bio-compatible, neutral, and recoverable mesoporous silica nanoparticles as a catalyst. The 4H-chromene derivatives were obtained in excellent yields by three component reaction of an aldehyde or isatin, malononitrile, and cyclic 1,3-diketones in ethanol at 60 °C.

Titanium dioxide nanoparticles as efficient catalyst for the synthesis of pyran’s annulated heterocyclic systems via three-component reaction

“…The results of our catalyst are compared with previous reports were performed with mesoporous silica nanoparticles [18], clinoptilolite zeolite [19], amino-functionalized silicagel [20], and choline hydroxide [21] as the catalysts with respect to their yields, solvents, and temperatures required for the reaction. As shown in Table 4, in the case of TiO 2 NPs the reaction yield is comparable with pervious work in milder reaction conditions.…”

“…In addition, some of them have been used as the antimalarial, antifungal, analgesics, and herbicidal agents [16,17]. Thus, development of new greener approaches for their synthesis is still of interest [18][19][20][21].…”

Leucine: green and efficient catalyst for the synthesis of 4H-chromenes

“…As a result, in recent years, much research activities in synthetic organic chemistry have been dedicated to the synthesis of 4H-chromenes due to their biological and pharmacological activities. Until now, several methods have been reviewed in the literature for the synthesis of 4H-chromenes that employ various reagents and catalysts such as n-Bu4NF [9], magnetic nanocatalysts [10], lipase [11], mesoporous silica nanoparticles [12], lithium bromide [13], piperidine [14], magnesium oxide [15], and silica-bonded n-propyl-4-aza-1-azoniabicyclo [2.2.2] octane chloride [16]. However, many of these procedures suffer from certain drawbacks such as environmentally unpleasant use of huge organic solvents and hazardous reagents, long reaction time, low yield, costly preparation of catalysts, and stringent reaction conditions.…”

Synthesis of mono- and bis-spiro-2-amino-4H-pyrans catalyzed by S-alkyl O-hydrogen sulfothioate functionalized silica-coated magnetic nanoparticles under ultrasound irradiation

“…Spirooxindole derivatives display various bioactive effects such as antitumor and antimicrobial, and as inhibitors of the human NKI receptor [6]. The existence of spiroindoline derivatives in the structure of organic compounds could potentially have novel therapeutic activities and thus there is an increased interest in obtaining spiro-2-amino-4H-pyrans containing oxindole moiety [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21].…”

“…This condensation has been catalyzed by a variety of reagents, such as ammonium salt [7], triethylbenzylammonium chloride (TEBA) [8], [BMIm]BF 4 [9], nano-MgO [10], InCl 3 /SiO 2 [11], (SB-DBU)Cl [12], alum [13], sodium stearate [14], SBA-Pr-NH 2 [15], L-proline [16], magnesium perchlorate [17], ethylenediamine diacetate [18,19], mesoporous silica nanoparticles [20], and sulfuric acid-modified poly(ethylene glycol) [21]. Also, this condensation has been performed in an electrocatalytic procedure [22].…”