An efficient green protocol for the synthesis of chalcones by a Claisen–Schmidt reaction using bismuth(III)chloride as a catalyst under solvent-free condition

Kumar, Dhruva; Suresh, Vignesh; Sandhu, Jagir S.

doi:10.1080/17518251003776893

Cited by 19 publications

(9 citation statements)

References 33 publications

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“…Chalcones have attracted attention due to numerous biological applications . The various types of catalysts are used for the synthesis of chalcones including bases such as NaOH, [9] KOH, LiOH.H 2 O and acids such as BF 3 .OEt, BiCl 3, clay, and sulfonic acid‐functional ionic liquids . The Knoevenagel reaction of aldehydes with active methylene compounds has been widely employed in the synthesis of several fine chemicals, intermediates of anti‐hypertensive drugs and calcium antagonists .…”

Section: Introductionmentioning

confidence: 99%

Nano‐structured Magnesium Oxide as Efficient Recyclable Catalyst for Knoevenagel and Claisen‐Schmidt Condensation Reactions

Roy

Panda

et al. 2016

ChemistrySelect

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Nano‐structured magnesium oxide was prepared by calcining its hydromagnesite phase, obtained by simple precipitation using magnesium acetate and ammonium carbonate under ambient condition. This MgO was used as active and reusable catalyst for the Knoevenagel condensation of aromatic aldehydes with malononitrile and ethylcyanoacetate under solvent‐free conditions at room temperature. It also exhibits strong activity in solvent‐free base catalyzed Claisen‐Schmidt condensation of various substituted benzaldehydes with acetophenone. The basic sites of different strengths like surface hydroxyl groups, and low coordination O2− sites may be responsible for the above catalytic activity. The experimental results showed that the nano‐MgO has high catalytic activity and can be recycled without significant loss of its activity.

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Section: Introductionmentioning

confidence: 99%

Nano‐structured Magnesium Oxide as Efficient Recyclable Catalyst for Knoevenagel and Claisen‐Schmidt Condensation Reactions

Roy

Panda

et al. 2016

ChemistrySelect

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“…In order to increase the yield and to avoid the formation of by-products, several protocols relative to a Claisen-Schmidt condensation have been reported using different catalysts: solid NaOH (Rahman et al 2012 ), Ba(OH) 2 (Aguilera et al 1987 ), BF 3 .OEt 2 (Narender & Papi Reddy 2007 ), NH 4 Cl (Pal 2013 ), BiCl 3 (Kumar & Sandhu 2010 ), InCl 3 (Deng & Ren 2003 ), TiCl 3 (SO 3 CF 3 ) (Iranpoor et al 1999 ), Yb(OTf) 3 (Wang et al 2004 ), FeCl 3 (Zhang et al 2003 ), molecular iodine (Sashidhara et al 2009 ) or Co(II)-bipyridyl (Irie & Watanabe 1981 ). Sonochemical or microwaves irradiation methods have been reported using basic or acidic alumina (Esmaeili et al 2005 ), Na 2 CO 3 -TBAB (PTC conditions) (Bogdal & Loupy 2008 ) and bis (p-methoxyphenyl)telluroxide (Zheng et al 1997 ) as catalysts.…”

Section: Introductionmentioning

confidence: 99%

An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

2015

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A simple and direct method for the Claisen-Schmidt reaction to prepare functionalized α,β-unsaturated ketones has been developed. Microwave irradiation of aldehydes with acetone produces benzalacetones selectively without self-condensation product in very short reaction times and good yields.Graphical AbstractGraphics for use in the Table of Contents.Electronic supplementary materialThe online version of this article (doi:10.1186/s40064-015-0985-8) contains supplementary material, which is available to authorized users.

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“…In order to increase the yield and to avoid the formation of byproducts, several protocols relative to Claisen-Schmidt condensation have also been reported using different catalysts, sonochemical activation or microwaves irradiation. However, in all these conditions, side reactions start decreasing the yield of the desired product and entail further purification steps [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Consequently, we were particularly interested in developing an efficient preparation of benzalacetones from acetone and aromatic substituted aldehydes in basic conditions under microwave-activation.…”

Section: Introductionmentioning

confidence: 99%

<strong>Microwave Activated Synthesis of Benzalacetones and Study of Their Potential Antioxidant Activity Using Artificial Neural Networks Method</strong>

Rayar¹,

Goya-Jorge

Barigye

et al. 2015

Proceedings of MOL2NET, International Conference on Multidisciplinary Sciences

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The α,β-unsaturated ketones known as benzalacetones are an interesting class of compounds frequently used as key intermediates in organic synthesis. Due to their conjugated system, benzalacetone and derivatives have been described as radical scavengers with potential antioxidant properties. We report here a simple and direct method to prepare functionalized α,βunsaturated ketones via a microwaves activated Claisen-Schmidt reaction. The experimental protocol developed selectively produces benzalacetones without self-condensation product in very short reaction times and good yields. Interested in the biological properties of benzalacetones, we also studied the antioxidant potential of these compounds using an in silico study based on the DPPH• radical scavenging ability. The built mathematical model was based on the 0-3D DRAGON molecular descriptors and the artificial neural networks technique showing a correlation coefficient for the training set (2) = 0.71 , an external correlation coefficient (2) = 0.65. Unfortunately, the results obtained in the in-silico study revealed that SciForum Mol2Net, 2015, 1(Section B), pages 1-8, Proceedings 2 http://sciforum.net/conference/mol2net-1 synthesized benzalacetones have no antioxidant activity. The predicted results have been confirmed experimentally by an in vitro assay of DPPH• scavenging capacity.

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An efficient green protocol for the synthesis of chalcones by a Claisen–Schmidt reaction using bismuth(III)chloride as a catalyst under solvent-free condition

Cited by 19 publications

References 33 publications

Nano‐structured Magnesium Oxide as Efficient Recyclable Catalyst for Knoevenagel and Claisen‐Schmidt Condensation Reactions

Nano‐structured Magnesium Oxide as Efficient Recyclable Catalyst for Knoevenagel and Claisen‐Schmidt Condensation Reactions

An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones

<strong>Microwave Activated Synthesis of Benzalacetones and Study of Their Potential Antioxidant Activity Using Artificial Neural Networks Method</strong>

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