An efficient synthesis of pyrazole chalcones under solvent free conditions at room temperature

Kumar, Parvin; Kumar, Sunil; Husain, Khalid; Kumar, Ashwani

doi:10.1016/j.cclet.2010.07.019

Cited by 26 publications

(17 citation statements)

References 24 publications

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“…Sheike et al [12] have reported a conventional one-pot Claisen-Schmidt condensation for the synthesis of targeted dihydropyrazole derivatives using chalcones by a fast, mild, and high-yielding ultrasonic irradiation methodology with overall yields of 65-82%. However, www.prkm.co.uk while reactions with impressive high conversion are also realised using various homogeneous bases such as NaOH or KOH with pyrazolylpyrazolines yield of 90-92% [12,13], these reagents are corrosive, toxic, non-reusable and also produce neutralisation waste [14]. To solve the problem associated with homogeneous bases, a solid catalyst has been reported.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dihydropyrazole derivatives using modified calcium oxide as a solid basic catalyst

Tang

Zhang

Wang

et al. 2015

Progress in Reaction Kinetics and Mechanism

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A highly efficient method for the synthesis of dihydropyrazole derivatives has been established by using CaO as a solid basic catalyst. It was found that a 77.1% yield of 3,5-diphenyl-4,5-dihydropyrazole-1-carboxamide was obtained at ratio of aminourea hydrochloride/chalcone of 1.2:1 after 3 h at a reaction temperature of 65℃. The reaction efficiency was greatly enhanced, with the 3,5-diphenyl-4,5dihydropyrazole-1-carboxamide yield reaching 91.2%, when the commercial CaO was modified by benzyl bromide in a simple way. The effects of modification and reaction conditions on the yields as well as the mechanism were studied thoroughly. From the results of FTIR and thermogravity analysis characterisation, the modifier was shown to be bonded on the surface of CaO chemically, and almost no Ca(OH) 2 was formed during the modification process. The type of chalcone has a strong influence on the yield of dihydropyrazole derivative.

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Section: Introductionmentioning

confidence: 99%

Synthesis of dihydropyrazole derivatives using modified calcium oxide as a solid basic catalyst

Tang

Zhang

Wang

et al. 2015

Progress in Reaction Kinetics and Mechanism

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“…Numerous green solvent free synthetic methodologies have been used for synthesis of carbonyl compounds such as enols, enones, chalcones, acid chlorides, acyl bromides and their esters. Similarly many catalysts were employed for synthesis of above said compounds such as silica-sulphuric acid [1][2][3], anhydrous zinc chloride [4], clay [5], ground chemistry catalysts-grinding the reactants with sodium hydroxide [6], aqueous alkali in lower temperature [7], solid sulphonic acid from aqueous alkali in lower temperature [7], solid sulphonic acid from bamboo [8], barium hydroxide [9] anhydrous sodium bicarbonate [10], microwave assisted synthesis [11], Fly-ash:water [12], Fly-ash:H 2 SO 4 [13], thionyl chloride [14], NaOH-CTABr [15], ZnAAl Hydrotalcite adhere ionic liquid [16], silica sol-gel [17], natural phosphate modified with sodium nitrate [18], highly ordered mesoporous AlSBA-15ASO 3 H hybrid material [19], KOH [20], Iodine-Alumina [21], hydroxyapatite [22], and sulfated titania [23]. The quantitative structure-activity relationship and quantitative property relationship of the organic substrates have been studied from the spectral data associated with their molecular equilibration [24].…”

Section: Introductionmentioning

confidence: 99%

Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones

Subramanian¹,

Vanangamudi²,

Thirunarayanan

2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Pravin and co-workers compared the mechanochemical synthesis of pyrazolyl chalcones with a conventional synthetic method. They found that the former of these two required shorter reaction times, afforded higher yields of the desired chalcone products and proceeded smoothly at room temperature [18]. The success of the mechanochemical approach used in this case was attributed to the fact that solid-state reactions occur more efficiently and selectively than solution-phase reactions, because the molecules in a crystal lattice are arranged more tightly and regularly than those in the liquid state [19].…”

Section: Introductionmentioning

confidence: 99%

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

Fahmy

El‐Sayed

Hemdan

2016

Chemistry Central Journal

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BackgroundMechano heterocyclic chemistry (MCH) is a recent quickly growing technique in the synthesis of heterocycles and draws the attention of heterocyclic chemists towards the uses of grindstone technique in a solvent free green efficient synthesis of many heterocyclic systems. On the other hand, multicomponent approach has opened the door for the rapid and efficient one-step procedures to synthesize a wide range of complex targets. Azlactones have been reported to exhibit a wide range of pharmaceutical properties including immune suppressive, anticancer. Antimicrobial, antitumor, anti-inflammatory and antiviral. It also used as useful synthons in the synthesis of several small molecules, including amino acids and peptides.ResultsThe present work describes an efficient one step green synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) via the multi-component synthesis by the mechanochemical grinding of glycine, benzoyl chloride, an aromatic aldehyde and fused sodium acetate in the presence of drops of acetic anhydride. This process is green, simple to handle, step and atom efficient, economical and environmentally friendly, because it does not require a reaction solvent or heating, we introduced the yield economy [YE] as a metric to assess the conversion efficiency of grinding and conventional synthetic reactions of azlactones. The structures of the newly synthesized compounds were elucidated by elemental and spectral analyses.ConclusionIn conclusion, we have developed a simple, efficient and eco-friendly strategy for facile synthesis of azlactones. The key advantages of this strategy, over conventional approach, include its simple, solvent free conditions, as well as its facile work-up, high yield economy and environmental friendliness. It is also successful in achieving three of the green chemistry objectives of a solvent free operation, high atom economy and step efficient. Thus, combining the features of both economic and environmental advantages.Graphical abstractAn efficient one step green synthesis of azlactones via multicomponent synthesis by a mechanochemical grinding.

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An efficient synthesis of pyrazole chalcones under solvent free conditions at room temperature

Cited by 26 publications

References 24 publications

Synthesis of dihydropyrazole derivatives using modified calcium oxide as a solid basic catalyst

Synthesis of dihydropyrazole derivatives using modified calcium oxide as a solid basic catalyst

Hydroxyapatite catalyzed aldol condensation: Synthesis, spectral linearity, antimicrobial and insect antifeedant activities of some 2,5-dimethyl-3-furyl chalcones

Multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) using a mechanochemical approach

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