Organosilane sulfonated graphene oxide in the Biginelli and Biginelli-like reactions

Safari, Javad; Gandomi‐Ravandi, Soheila; Ashiri, Samira

doi:10.1039/c5nj01741f

Cited by 51 publications

(31 citation statements)

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“…Metal‐based heterogeneous catalysts such as polymers supported metal nanoparticles, ionic liquids, zeolites, acidic surfactants, ion exchange resins, Lewis acids, metal nanoparticles, urea, silica supported sulfonated graphene oxide, etc. are reported . Rate enhancement using ultrasound as well as microwaves is also been reported.…”

Section: Introductionmentioning

confidence: 90%

Role of Degree of Oxidation of Graphene Oxide on Biginelli Reaction Kinetics

et al. 2017

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The effect of varying degree of oxidation of graphene oxide on its catalytic activity for synthesis of dihydropyrimidinones via Biginelli reaction is investigated. Graphene oxide with varying degree of oxidation (GO‐x) was synthesized, and characterized to confirm the change in functional groups on GO surface with different amount of oxidizing agent used during synthesis. An increase in amount of oxidant, increases the percentage of oxygen in GO‐x, increasing the d‐spacing and thus enhancing the exfoliation of GO‐x. The carboxylic acid groups increase with increasing oxidation degree, while the proportion of hydroxyl groups is almost the same. GO‐x shows excellent activity towards catalysing Biginelli reaction. An increase in oxygen content in GO‐x improves its catalytic activity, which is attributed to the increased acidity in GO‐x. Reaction kinetics imply a second order reaction. GO‐x shows excellent recyclability with only marginal loss in activity on recycle.

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Section: Introductionmentioning

confidence: 90%

Role of Degree of Oxidation of Graphene Oxide on Biginelli Reaction Kinetics

et al. 2017

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“…We feel that this protocol is a valuable addition to the currently reported ones. [20][21][22][23][24][25] …”

Section: One-pot Synthesis Of 23-dihydroquinazolin-4(1h)-ones Under mentioning

confidence: 98%

“…26 All of these reactions are successful in producing the target compound although certain drawbacks, such as use of harmful solvents, expensive catalysts, and low yields, are associated with some of them. With the goal of making some of the above-mentioned methods benign, the reactions were carried out under solvent-free conditions 16,20,21 , using MW-irradiation 21,22 and of water 18,22,24,25 or ethanol 11,12,17,22 as solvents. However, none of them proceeded without the use of catalyst.…”

Section: One-pot Synthesis Of 23-dihydroquinazolin-4(1h)-ones Under mentioning

confidence: 99%

“…Furthermore, the reaction conditions are sufficiently mild enough to tolerate a variety of functionalities such as Cl, Br, OH, OMe, -OCH 2 O-and NMe 2 . All the products (3) are known compounds and were identified by comparison of their physical and spectral data with those reported in the literature [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26]33 . From a mechanistic point of view, the process is possibly a general acidbase catalyzed condensation followed by cyclization 16,20 .…”

Section: One-pot Synthesis Of 23-dihydroquinazolin-4(1h)-ones Under mentioning

confidence: 99%

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One-pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones under Catalyst- and Solvent-free Conditions

Gupta

Samanta

Mallik

2015

Organic Preparations and Procedures International

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Small heterocyclic rings constitute one of the richest sources of diversity for medicinal chemists and more than half of biologically active molecules belong to various categories of quinazolinones. 1 Among them, 2,3-dihydro-4(1H)-quinazolinones remain a major source for the design of therapeutic drugs. 2 Moreover, they are building blocks for more than 150 naturally occurring pharmacologically active alkaloids and commercial drugs. 3,4 Their pharmaceutical character include anti-malarial, 5 anti-bacterial, 6 anti-tumor, 7 anticancer, 8 anti-fungal, 8 anti-convulsant 9 and monoamine oxidase inhibitory activities. 10 There are a number of methods for preparation of this class of compounds, the most direct one involving the condensation of aryl, alkyl, and heteroaryl aldehydes with anthranilamide in the presence of catalysts and solvents such as NH 4 Cl, 11 NaHSO 4 , 12 b-cyclodextrin, 13 cellulose-SO 3 H, 14 Amberlyst 15, 15 [PYC 4 SO 3 H][HSO 4 ]/A300SiO 2 , 16 Sc(OTf) 3 , 17 heteropoly acids, 18 cyanuric chloride, 19 transition metal-carbon nanotube (M-CNT) nanocomposites, 20,21 2-morpholinoethanesulfonic acid, 22 propylphosphonic anhydride (T3P Ò ), 23 K 3 PO 4 .H 2 O, 24 p-sulfonic acid calix[4]arene 25 or trifluoroethanol. 26 All of these reactions are successful in producing the target compound although certain drawbacks, such as use of harmful solvents, expensive catalysts, and low yields, are associated with some of them. With the goal of making some of the above-mentioned methods benign, the reactions were carried out under solvent-free conditions 16,20,21 , using MW-irradiation 21,22 and of water 18,22,24,25 or ethanol 11,12,17,22 as solvents. However, none of them proceeded without the use of catalyst. The current trend towards development of catalystfree 27-29 and solvent-free 30-32 reaction conditions encouraged us to study the same reaction without the use any catalyst or solvent. The remarkable success obtained in this investigation is presented herein.Our present methods involve subjecting an intimate mixture of anthranilamide and aldehyde/ketone (1:1 mole ratio) directly to heat (120 C, 10 min) or microwave (300 W, 3 min) irradiation. The time and temperature for the thermal reaction and the time and power for the MWI process were then optimized ( Table 1). A range of structurally diverse aryl and heteroaryl aldehydes and two cyclic ketones were examined and gave the target compounds 3 (Scheme 1) in yields greater than 90% ( Table 2).In the methods reported, it was a common observation that the reactions were very clean, and no side-products were formed in any run. In fact, the crude products obtained were of high purity and did not require any chromatographic separation; crystallization

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“…Therefore various procedures have been developed for preparing this important class of compounds. 19 Other methods including synthesis of 2,3-dihydroquinazoline 4(1H)-ones via one-pot threecomponent reaction catalyzed by L-pyrrolidine-2-carboxylic acid-4-hydrogen sulfate (supported on silica gel), 20 Cu-CNTs, 21 copper-catalyzed, 22 Ce(CH3SO3)3 • 2H2O, 23 montmorillonite K-10, 24 MCM-41-SO3H, 25 gallium triflate, 26 were also reported. However, most of the synthetic protocols reported so far suffer from drawbacks such as low yields, long reaction times, the use of expensive or toxic metal salts as catalysts, the use of toxic solvents and tedious work-up procedures.…”

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confidence: 99%

Incredible Role of Glycerol in Multicomponent Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones and 1-Amidoalkyl-2-naphthols

Hajjami¹,

Bakhti²,

Ghiasbeygi³

2015

Croat. Chem. Acta

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Abstract. An efficient and green synthesis of 1-amidoalkyl-2-naphthols via one-pot three-component condensation of aromatic aldehydes, acetamide and 2-naphthol in the presence of catalytic amounts of glycerosulfonic acid in glycerol as a green solvent was elaborated. Also a simple method for the one-pot threecomponent synthesis of 2,3-dihydroquinazoline-4(1H)-ones using of isatoic anhydride, aldehydes and ammonium acetate in the presence of glycerol as a green catalyst and solvent was described. In this light we introduced the brilliant and valuable role of glycerol in the synthesis of 2,3-dihydroquinazoline-4(1H)-ones and 1-amidoalkyl-2-naphthols.

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Organosilane sulfonated graphene oxide in the Biginelli and Biginelli-like reactions

Abstract: The acid functionalized SSi-GO was used as a highly active, selective and reusable catalyst to improve the formation of pyrimidinones.

Cited by 51 publications

References 71 publications

Role of Degree of Oxidation of Graphene Oxide on Biginelli Reaction Kinetics

Role of Degree of Oxidation of Graphene Oxide on Biginelli Reaction Kinetics

One-pot Synthesis of 2,3-Dihydroquinazolin-4(1H)-ones under Catalyst- and Solvent-free Conditions

Incredible Role of Glycerol in Multicomponent Synthesis of 2,3-Dihydroquinazoline-4(1H)-ones and 1-Amidoalkyl-2-naphthols

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