Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh<sub>2</sub>) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction

Valizadeh, Hassan; Gholipour, Hamid

doi:10.1080/00397910903097310

Cited by 28 publications

(9 citation statements)

References 28 publications

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“…The Knoevenagel condensation of aldehydes with active methylene compounds gives rise to the corresponding alkene derivatives. This condensation can be easily conducted in the presence of a variety of catalysts including Lewis acids [140], zeolites [141], amine-functionalized materials [142][143][144], ionic liquids [145,146], and nanomaterials [147,148], each of which gives variable yields of the Knoevenagel adducts. In addition, solid bases [149,150] and organic bases, for example piperidine, pyridine, urea, DABCO, and guanidine [151][152][153], have been used for Knoevenagel condensations.…”

Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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A variety of 4H-chromenes, benzochromenes, 4,5-dihydropyrano[3,2-c]chromenes, 4H-pyran-3-carboxylates, and 3,4-disubstituted isoxazol-5(4H)-ones have been synthesized in high yields by using potassium hydrogen phthalate (KHP) as an inexpensive, commercially available catalyst. It was found that the threecomponent tandem reaction enabled synthesis of pyran-annulated heterocycles in water at 50°C. 3,4-Disubstituted isoxazol-5(4H)-ones were synthesized by use of 10 mol% KHP in water at room temperature. Also, treatment of methylene-containing compounds (malononitrile or ethyl cyanoacetate) with aromatic aldehydes in the presence of 5 mol% KHP resulted in a,b-unsaturated nitriles. The procedure is an easily performed, straightforward method for synthesis of a variety of pyranannulated compounds, isoxazol-5(4H)-one-containing heterocycles, and Knoevenagel adducts. The reaction is safe, uses mild conditions, and is environmentally benign. Other notable advantages are reuse of the catalyst, no use of hazardous organic solvents, and ease of work-up.

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Section: Introductionmentioning

confidence: 99%

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Kiyani

Ghorbani

2014

Res Chem Intermed

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“…Furthermore, use of dual functional ionic liquids for the condensation has been communicated by various research groups [27,28]. We have also previously reported the Knoevenagel reaction in various ionic liquids [29][30][31].…”

Section: Introductionmentioning

confidence: 94%

A Simple and Efficient Procedure for Knoevenagel Reaction Promoted by Imidazolium-Based Ionic Liquids

Hu¹,

Ngwa²,

Zheng³

2015

COS

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Various room temperature ionic liquids (RTILs), notably, 1-methoxyethyl-3-methylimidazolium trifluoroacetate [MeOEtMIM] + [CF 3 COO]¯ , have been used to promote the Knoevenagel condensation to afford substituted olefins. All reactions proceeded effectively in the absence of any other catalysts or co-solvents with good to excellent yields. This method is simple and applicable to reactions involving a wide range of aldehydes and ketones with methylene compounds. The ionic liquid can be recycled without noticeable reduction of its catalytic activity. A plausible reaction mechanism is proposed.

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“…Many convenient synthetic methods have been described, including Pechmann [7], Perkin [8], Knoevenagel condensation [9], Reformatsky [10], and Wittig reactions [11]. Recent reports of the synthesis of coumarin derivatives include the use of metal triflates in qFriedel-Crafts alkenylations of aromatic compounds with various alkyl-and aryl-substituted alkynes [12], hydroarylation of arylpropionic acid methyl esters having a methoxymethyl acetal (MOM) protected hydroxy group with various arylboronic acids in the presence of a catalytic amount of CuOAc [13], reaction of substituted phenyl acetic acids and substituted 2-hydroxy benzaldehydes in the presence of cyanuric chloride (2,4,6-trichloro-1,3, 5-triazine) and N-methyl morpholine [14], palladium-catalyzed oxidative cyclocarbonylation of 2-vinylphenols [15], condensation of aroylketene dithioacetals, and 2-hydroxybenzaldehydes in the presence of a catalytic amount of piperidine [16], or reaction of 2-hydroxybenzaldehydes, triphenylphosphine, and dialkyl acetylenedicarboxylate via vinyltriphenylphosphonium salt-mediated aromatic electrophilic substitution [17].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors

Kozak

Daśko

Masłyk

et al. 2015

Journal of Asian Natural Products Research

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Steroid sulfatase (STS) enzyme inhibition is an important approach to the management of hormone-dependent breast cancer. In this paper, we report convenient methods for the synthesis and biological evaluation of thiophosphate tricyclic coumarin analogs exhibiting STS activity. The described methods are based on the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-2-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one, and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one and their further modification by the introduction of various thiophosphate moieties. The inhibition properties of the synthesized compounds were tested toward STS isolated from human placenta. Most of the new STS inhibitors possessed good to moderate activity toward STS. During the course of our investigation, the largest inhibitory effects in the STS enzyme assays were observed for the two compounds 3f and 4r, with IC50 values of 13.3 and 30.3 μM, respectively (the IC50 value of 1 μM for the 665-COUMATE was used as a reference). The structure-activity relationships of the synthesized coumarin derivatives toward STS enzymes are discussed.

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Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh₂) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction

Cited by 28 publications

References 28 publications

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

A Simple and Efficient Procedure for Knoevenagel Reaction Promoted by Imidazolium-Based Ionic Liquids

Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors

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Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh2) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction

Cited by 28 publications

References 28 publications

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

Efficient tandem synthesis of a variety of pyran-annulated heterocycles, 3,4-disubstituted isoxazol-5(4H)-ones, and α,β-unsaturated nitriles catalyzed by potassium hydrogen phthalate in water

A Simple and Efficient Procedure for Knoevenagel Reaction Promoted by Imidazolium-Based Ionic Liquids

Synthesis and biological evaluation of thiophosphate tricyclic coumarin derivatives as steroid sulfatase inhibitors

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Imidazolium-Based Phosphinite Ionic Liquid (IL-OPPh₂) as Reusable Catalyst and Solvent for the Knoevenagel Condensation Reaction