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| Chalcone Synthesis and Applications: A Review | |||||||
| Paper Id :
16270 Submission Date :
18/07/2022 Acceptance Date :
22/07/2022 Publication Date :
25/07/2022
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| Abstract | Chalcones are natural pigments have a wide spectrum of biological activities, which are of great interest in many fields. The presence of a reactive α,β-unsaturated carbonyl function in chalcones and its derivatives is the reason for their pharmacological activities. Chalcones can be synthesized by claisen-schmidts condensation, aldol condensation and using microwave irradiation. | ||||||
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| Keywords | Chalcones, Claisen-Schmidts Condensation, Aldol Condensation, Microwave Irradiation. | ||||||
| Introduction |
The chalcones are natural pigments having α,β -unsaturated carbonyl system.[1-5] They are used in synthesis of wide variety of cyclic and heterocyclic compounds.[6-10] |
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| Aim of study | Chalcones are open chain flavonoids containing an enone system. In the enone system the carbonyl group [electron attracting group] is in conjugation with carbon-carbon double bond, which activates the α-carbon atom towards nucleophilic reagents. The nucleophilic addition in chalcone system takes place by following mechanism. | ||||||
| Review of Literature | The term chalcone was coined by
Kostanecki and Tamber. Chemically chalcones are named as benzylidine
acetophenones, α-phenyl, β-benzolethylene, phenyl styryl ketones, β-phenyl
acrylophenone, 1,3-diphenylprop-2-en-1-one. |
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| Main Text |
The chalcones are important Michael acceptors having enone system, whose polar character increases due to introducing aromatic substituents and enhance their tendency to undergo Michael condensation. Besides their synthetic utility a wide spectrum of biological activities of chalcones have been reported due to the presence of heterocyclic nuclei in the enone system. Chalcones and their derivatives possess antibacterial[11,12], anticancer[13], anti-inflammatory, analgesic, antituburcular[14-16], anti-HIV[17] activities. Synthesis
of chalcones Claisen-
Schmidt condensation The chalcones are synthesized by Claisen Schmidt Condensation[18, 19] of ketone with aldehyde in the presence of alkali base or in the presence of alcoholic alkali.
Aldol
Condensation
The reaction of acetophenone and benzaldehyde in the presence of KOH give chalcone as a product.
Microwave
Assisted Synthesis of Chalcones In
the last decade, Microwave Irradiation[20, 21] have been used more
and more often in organic synthesis. Heterogeneous catalyst such as K2CO3,
Ba(OH)2, piperidine and aqueous alkali are used to synthesize
chalcones and their derivatives using microwave. Synthetic application of chalcones Cyclic
system
Chalcones react with cyclopentanone in the presence of Ba(OH)2 and give complex domino products.[22]
Heterocyclic
systems
Substituted and unsubstituted 2,4-di-5-oxo-5,6,7,8-tetrahydro-2-chromones have been synthesized using anhydrous zinc chloride as catalyst.[23]
Oxidation of 2’-hydroxy chalcones with molar amount of mercury (II) acetate in presence of pyridine and with catalytic amount of CuBr2 in DMSO has been reported to afford aurones in excellent yields.[24]
Synthesis of 2,4,6-triaryl pyridine has been achieved using a novel reaction between chalcones and ammonium acetate under solvent free condensation.[25]
Microwave
Induced Synthesis of Heterocycles using chalcones
A number of cyclic and heterocyclic systems using chalcones under microwave irradiation can be achieved very conveniently in excellent yields. 3- benzimidazolyl-5-aryl-2-isoxali has been synthesized using MWI by the interaction between benzimidazolyl chalcoles and hydroxylamine hydrochloride in presence of pyridine.[26]
Microwave
assisted transformation
A series of new [3-(2-hydroxy phenyl)-5-aryl-2-pyrazolin-2-yl]-4-thiazolidinones has been prepared[27] by microwave induced reaction of N’-chloroacetyl-3, 5-diaryl-2-pyrazolines with ammonium thiocyanate.
Microwave assisted transformation of some benzimidazolyl chalcones into N’-substituted pyrazolines and evaluation of their antibacterial activities has been reported recently by Rajora et al.[28]
Various
N- substituted pyrazoline derivatives have been synthesized by the condensation
of chalcones with hydrazine hydrate using ethanol as a solvent under MWI. |
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| Conclusion | From this review it can be stated that chalcones and their derivatives have a great applications in chemical fields like coordination chemistry as a legend, medical chemistry as antibacterial, anticancer, antifungal, in analytical chemistry as a reagents and other uses. | ||||||
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