Chalcones: Versatile intermediates in heterocyclic synthesis

Abstract

Chalcones are a fascinating and well‐studied group of organic molecules. Synthesis of chalcones has been one of the essential areas of organic synthesis over the last few decades because of their immense therapeutic and excellent photophysical properties. Furthermore, these chalcone derivatives can be utilized to make a variety of heterocyclic compounds, especially five‐ and six‐membered heterocycles. Heterocyclic compounds have a long history in chemistry, primarily in pharmaceuticals. However, synthesizing some specific heterocyclic molecules remains challenging and requires multistep processes with few possible intermediates. Chalcones can be considered as one of the most useful, readily available intermediates in heterocyclic synthesis. Herein, the synthesis of various potential heterocyclic compounds using chalcones as an intermediate is elaborated. This review shows the untapped potential of chalcones in organic synthesis. Also, it will assist the chemist in designing new heterocycles by adopting these strategies.

Synthesis, reactions and application of chalcones: a systematic review

“…This journal is © The Royal Society of Chemistry 2023 4.2.1.6.2.Aza-Michael addition of hydrazine derivatives and hydroxylamine to chalcones Many biologically active pyrazoles and isoxazoles have been generated by the interaction of chalcones with hydrazine derivatives or hydroxyl amines. 129,130 The usage of pyrazoles as antioxidants in fuels, anesthetics, and agricultural uses, as well as in pharmaceuticals and dyes, 131 has attracted attention from researchers. [132][133][134] These substances are helpful for materials chemistry, brightening, and electroluminescence.…”

“…The biological uses of triazole derivatives include as anticonvulsants, antimicrobials, antivirals, antituberculars, antidiabetics, anti-inflammatories, antiproliferatives, antioxidants, anti-ureases, and antimalarials. 129,166 Triazoles are produced when the chalcone undergoes a [3 + 2] cycloaddition reaction with azide molecules. 167,168 Moreover, it was reported that the [3 + 2] cycloaddition reaction of chalcone 123 with 5-azido-5deoxy-1,2-O-isopropylidene-α-D-xylofuranose 124 using tetrabutylammonium hydrogen sulfate (TBAHS) as a catalyst yielded triazole 125, as shown in Scheme 41.…”

“…149–159 The reaction of chalcone with guanidine, urea or thiourea forms pyrimidine derivatives. 129,160,161 As shown in Scheme 38, chalcone 116 was reported to yield pyrimidine derivative 117 when treated with urea in ethanolic sodium hydroxide. 129 Moreover, aryl chalcone 40 reacted with urea and thiourea to yield pyrimidine derivatives 118 and 119 (Scheme 39).…”

DBU-catalyzed diastereoselective 1,3-dipolar [3+2] cycloaddition of trifluoroethyl amine-derived isatin ketimines with chalcones: synthesis of 5′-CF3-substituted 3,2′-pyrrolidinyl spirooxindoles

“… 6 Additionally, owing to their facile synthetic accessibility and ɑ,β-unsaturated carbonyl conjugated system containing two electrophilic centers, they are frequently used as valuable intermediates for the formation of heterocycles, particularly five- and six-membered heterocyclic molecules. 7 Considering the importance of spirooxindoles, fluorine compounds, and chalcones, we hypothesized that their integration could augment the bioactivities. However, to date, there have been few successful examples employing the chalcone-type compounds as the dipolarophiles for the diastereoselective 1,3-dipolar [3 + 2] cycloaddition involving the ketimines 1 ( Scheme 1b ).…”

Design, synthesis, X-ray crystal structures, anticancer, DNA binding, and molecular modelling studies of pyrazole–pyrazoline hybrid derivatives

“…4,5 Commonly referred to as chalcones, a-b unsaturated ketones are a signicant family of natural products as well as synthetic chemicals that have shown a variety of biological activity. 6,7 However, not many ways for derivatizing avonoids, particularly chalcones, under Suzuki cross-coupling conditions have been reported. [8][9][10] As parent heterocycles of several commercially available medications, pyrazoline and pyrazole heterocycles have unique biological properties.…”