Nano silica-bonded aminoethylpiperazine: a highly efficient and reusable heterogeneous catalyst for the synthesis of 4H-chromene and 12H-chromeno[2,3-d]pyrimidine derivatives

Tajbakhsh, Mahmood; Kariminasab, Mohaddeseh; Alinezhad, Heshmatollah; Hosseinzadeh, Rahman; Rezaee, Parizad; Tajbakhsh, Mahgol; Gazvini, Helia Janatian; Amiri, Mohammadreza Azizi

doi:10.1007/s13738-015-0607-y

Cited by 15 publications

(2 citation statements)

References 38 publications

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“…It is worth noting that solvent-free conditions have also been reported to make some of the 2-amino-3cyano-4H-pyrans. The use of catalysts [52][53][54][55][56][57][58][59] or ionic liquids [60-62] appears to provide a similar reaction outcome from the viewpoint of green chemistry. However, most of the methods suffer from one or several drawbacks like harsh reaction conditions, use of a large quantity of the catalyst, tedious workup procedure and low substrate scope studies.…”

Section: Introductionmentioning

confidence: 99%

One-pot Multicomponent Green Chemistry Approach: Sodium Fluoride-Catalysed Highly Efficient Microwave Irradiation-Assisted Synthesis of Substituted Chromene Derivatives in Aqueous Medium

Fabitha

Arya

Chandrakanth

et al. 2022

Preprint

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2-Amino-4H-benzo[h]chromene-3-carbonitrile and 2-amino-5-oxo-4H,5H-pyrano[3,2-c]chromene-3-carbonitrile are two important pharmacophores with extensive applications in medicinal chemistry. The multicomponent Knoevenagel-Michael reaction is one of the most efficient strategies to construct these two scaffolds. Previous efforts have been made in converting the traditional organic solvents to eco-friendly solvents including H2O generally in the presence of complex catalysts. Here we present our work of using sodium fluoride (NaF) as the catalyst to synthesize a wide scope of the two types of substrates starting from α- or β-naphthol or 4-hydroxycoumarin. Using 12 mol% NaF under the microwave irradiation condition, the reactions were completed within 15–25 min with all the yields exceeding 85%. The reaction products were purified simply by washing with H2O and can be further purified by crystallization with MeOH. The analysis of green chemistry-related parameters suggested that the current method was highly environmentally benign, highlighting the potential of this method in the use of drug discovery and development.

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Section: Introductionmentioning

confidence: 99%

One-pot Multicomponent Green Chemistry Approach: Sodium Fluoride-Catalysed Highly Efficient Microwave Irradiation-Assisted Synthesis of Substituted Chromene Derivatives in Aqueous Medium

Fabitha

Arya

Chandrakanth

et al. 2022

Preprint

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“…11,12 In addition, tetraketones are also extensively used as important precursors for the synthesis of various acridinediones as laser dyes, 13,14 DNA intercalator, 15 electron donors and acceptors [16][17][18] of the photoinitiated polymerization of acrylates and methacrylates, 19 and synthesis of some heterocyclic compounds. [20][21][22][23] Due to our interest in developing a new synthesis in the field of catalyst applications, [24][25][26][27] herein, we explore the catalytic activity of SiO 2 NPs as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H -perimidines as well as tetraketones. In this work 4-(2,3-dihydro-1H -perimidin-2yl)benzonitrile and 2-(pyridin-4-yl)-2,3-dihydro-1Hperimidine are synthesized as new compounds.…”

Section: Introductionmentioning

confidence: 99%

Application of $$\hbox {SiO}_{{2}}$$ SiO 2 nanoparticles as an efficient catalyst to develop syntheses of perimidines and tetraketones

2019

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In this paper, we explore the catalytic activity of SiO 2 nanoparticles (NPs) as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H -perimidines as well as tetraketones. For tetraketones syntheses, a simple tandem Knoevenagel condensation following Michael addition procedure is performed by the reaction between benzaldehydes and 5,5-dimethyl-1,3-cyclohexanediones under solvent-free condition using SiO 2 NPs as an efficient solid catalyst. In addition, for 2,3-dihydro-1H -perimidines syntheses, cyclocondensation of various aldehydes with 1,8-diaminonaphthalene is achieved under solvent-free condition using SiO 2 NPs as a catalyst at room temperature. The results showed catalytic enhancement in both synthetic procedures. In this work, 4-(2,3-dihydro-1H -perimidin-2-yl)benzonitrile and 2-(pyridin-4-yl)-2,3-dihydro-1Hperimidine are synthesized as new compounds. Also, reusability study of SiO 2 NPs was done to ensure its applicability as a recycled catalyst in this work.

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Ferrocene‐tagged ionic liquid stabilized on silica‐coated magnetic nanoparticles: Efficient catalyst for the synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives under solvent‐free conditions

Teimuri‐Mofrad

Gholamhosseini-Nazari

Payami

et al. 2017

Applied Organom Chemis

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An advanced novel magnetic ionic liquid based on imidazolium tagged with ferrocene, a supported ionic liquid, is introduced as a recyclable heterogeneous catalyst. Catalytic activity of the novel nanocatalyst was investigated in one-pot three-component reactions of various aldehydes, malononitrile and 2-naphthol for the facile synthesis of 2-amino-3-cyano-4H-pyran derivatives under solventfree conditions without additional co-catalyst or additive in air. For this purpose, we firstly synthesized and investigated 1-(4-ferrocenylbutyl)-3- . The synthesized novel catalyst was characterized using 1 H NMR, 13 C NMR, Fourier transform infrared and energy-dispersive X-ray spectroscopies, X-ray diffraction, and transmission and field emission scanning electron microscopies. Combination of some unique characteristics of ferrocene and the supported ionic liquid developed the catalytic activity in a simple, efficient, green and eco-friendly protocol. The catalyst could be reused several times without loss of activity.

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Nano silica-bonded aminoethylpiperazine: a highly efficient and reusable heterogeneous catalyst for the synthesis of 4H-chromene and 12H-chromeno[2,3-d]pyrimidine derivatives

Cited by 15 publications

References 38 publications

One-pot Multicomponent Green Chemistry Approach: Sodium Fluoride-Catalysed Highly Efficient Microwave Irradiation-Assisted Synthesis of Substituted Chromene Derivatives in Aqueous Medium

One-pot Multicomponent Green Chemistry Approach: Sodium Fluoride-Catalysed Highly Efficient Microwave Irradiation-Assisted Synthesis of Substituted Chromene Derivatives in Aqueous Medium

Application of $$\hbox {SiO}_{{2}}$$ SiO 2 nanoparticles as an efficient catalyst to develop syntheses of perimidines and tetraketones

Ferrocene‐tagged ionic liquid stabilized on silica‐coated magnetic nanoparticles: Efficient catalyst for the synthesis of 2‐amino‐3‐cyano‐4H‐pyran derivatives under solvent‐free conditions

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