Preparation and characterization of magnetite-dihydrogen phosphate as a novel catalyst in the synthesis of tetrahydrobenzo[b]pyrans

Saadati-Moshtaghin, Hamid Reza; Zonoz, Farrokhzad Mohammadi

doi:10.1016/j.matchemphys.2017.06.066

Cited by 33 publications

(8 citation statements)

References 29 publications

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“…A modest decrease in the catalytic activity as shown in Figure 5 after six runs was evident by the percentage yields of each recycle. These results indicate the reusability of MGO-D-NH-(CH 2 ) 4 -SO 3 H. [69] 120 96 H 2 PO 4 -SCMNPs/solvent-free, 80°C [70] 20 92 Fe 3 O 4 @Ph-SO 3 H/H 2 O/r.t./ultrasonic condition [71] 25 95 MGO-D-NH-(CH 2 ) 4 -SO 3 H/H 2 O-EtOH (4:1), r.t. (this work) 5 95…”

Section: Recycling Of Catalystmentioning

confidence: 88%

SO₃H‐functionalized nano‐MGO‐D‐NH₂: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

Alinezhad

Tarahomi

Maleki

et al. 2019

Applied Organom Chemis

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An SO3H‐functionalized nano‐MGO‐D‐NH2 catalyst has been prepared by multi‐functionalization of a magnetic graphene oxide (GO) nanohybrid and evaluated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3‐d]pyrimidinone derivatives. The GO/Fe3O4 (MGO) hybrid was prepared via an improved Hummers method followed by the covalent attachment of 1,4‐butanesultone with the amino group of the as‐prepared polyamidoamine‐functionalized MGO (MGO‐D‐NH2) to give double‐functionalized magnetic nanoparticles as the catalyst. The prepared nanoparticles were characterized to confirm their synthesis and to precisely determine their physicochemical properties. In summary, the prepared catalyst showed marked recyclability and catalytic performance in terms of reaction time and yield of products. The results of this study are hoped to aid the development of a new class of heterogeneous catalysts to show high performance and as excellent candidates for industrial applications.

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Section: Recycling Of Catalystmentioning

confidence: 88%

SO₃H‐functionalized nano‐MGO‐D‐NH₂: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

Alinezhad

Tarahomi

Maleki

et al. 2019

Applied Organom Chemis

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“…Moshtaghin and Zonoz [ 94 ] have constructed a magnetite-2H-phosphate (H 2 PO 4 @SCMNPs) to be used as a green heterogeneous catalyst for the preparation of 4 H -benzopyran ( 119 ) analogues. Several instrumental techniques, such as FT-IR, SEM, TEM and XRD, revealed the inverse cubic spinel with a magnetite core covered with a silica shell adhered to dihydro phosphate moiety with a particle size ranging from 60–80 nm.…”

Section: Synthesis Of Pyran Derivativesmentioning

confidence: 99%

Recent Progress in the Multicomponent Synthesis of Pyran Derivatives by Sustainable Catalysts under Green Conditions

2022

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Pyrans are one of the most significant skeletons of oxygen-containing heterocyclic molecules, which exhibit a broad spectrum of medicinal applications and are constituents of diverse natural product analogues. Various biological applications of these pyran analogues contributed to the growth advances in these oxygen-containing molecules. Green one-pot methodologies for synthesising these heterocyclic molecules have received significant attention. This review focuses on the recent developments in synthesising pyran ring derivatives using reusable catalysts and emphasises the multicomponent reaction strategies using green protocols. The advantages of the catalysts in terms of yields, reaction conditions, and recyclability are discussed.

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“…They are also broadly used in perfumes, cosmetics, agrochemicals and in food as additives [28, 29]. Literature reveals reports for synthesis of benzopyrans using with various catalysts like hexamethylenetetraminebromine [30], magnetite-dihydrogen phosphate [31], Bmim[BF 4 ] [32], PPA-SiO 2 [33], Ca(OTf) 2 :Bu 4 NPF 6 [34], phenylboronic acid [35] and H 6 P 2 W 12 O 62 ·H 2 O [36], MWI/PEG [37] etc. Previously reported procedures come with various limitations, like use of expensive reagents/catalysts, toxic solvents, strict reaction conditions, low product yields, long reaction times and nonrecyclability of catalysts, which confine their scope in practical applications (details in Additional file 1: Table S1).…”

Section: Introductionmentioning

confidence: 99%

A facile and one-pot synthesis of new tetrahydrobenzo[b]pyrans in water under microwave irradiation

Khumalo¹,

Maddila²,

Jonnalagadda³

2019

BMC Chemistry

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Eleven new tetrahydrobenzo[b]pyran derivatives were synthesized via a three component reaction of different aromatic aldehydes, methyl cyanoacetate and 1,3-cyclohexadione, with water as solvent under catalyst-free microwave irradiation. The structures of all the new molecules were well analysed and their structures established by using various spectral techniques (1H NMR, 13C NMR, 15N NMR and HRMS). Various advantages of reported protocol are the ease of preparation, short reaction times (10 min), aqueous solvent and excellent yields (89–98%). Additionally, this method provides a clean access to the desired products by simple workup.

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Preparation and characterization of magnetite-dihydrogen phosphate as a novel catalyst in the synthesis of tetrahydrobenzo[b]pyrans

Cited by 33 publications

References 29 publications

SO₃H‐functionalized nano‐MGO‐D‐NH₂: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

SO₃H‐functionalized nano‐MGO‐D‐NH₂: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

Recent Progress in the Multicomponent Synthesis of Pyran Derivatives by Sustainable Catalysts under Green Conditions

A facile and one-pot synthesis of new tetrahydrobenzo[b]pyrans in water under microwave irradiation

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Preparation and characterization of magnetite-dihydrogen phosphate as a novel catalyst in the synthesis of tetrahydrobenzo[b]pyrans

Cited by 33 publications

References 29 publications

SO3H‐functionalized nano‐MGO‐D‐NH2: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

SO3H‐functionalized nano‐MGO‐D‐NH2: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

Recent Progress in the Multicomponent Synthesis of Pyran Derivatives by Sustainable Catalysts under Green Conditions

A facile and one-pot synthesis of new tetrahydrobenzo[b]pyrans in water under microwave irradiation

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SO₃H‐functionalized nano‐MGO‐D‐NH₂: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media

SO₃H‐functionalized nano‐MGO‐D‐NH₂: Synthesis, characterization and application for one‐pot synthesis of pyrano[2,3‐d]pyrimidinone and tetrahydrobenzo[b]pyran derivatives in aqueous media