Catalytic Enantioselective Addition of Sodium Bisulfite to Chalcones

Moccia, Maria; Fini, Francesco; Scagnetti, Michela; Adamo, Mauro F. A.; Ricci, Alfredo

doi:10.1002/ange.201102162

Cited by 13 publications

(3 citation statements)

References 37 publications

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“…The desired sulfonic acids (7) were synthesized in high yields (87−97%) and with excellent enantioselectivity (84−99%) (Scheme 14). 176 5.1.2. Aminohalogenations of Chalcones.…”

Section: Michael Additionmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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Privileged structures have been widely used as an effective template in medicinal chemistry for drug discovery. Chalcone is a common simple scaffold found in many naturally occurring compounds. Many chalcone derivatives have also been prepared due to their convenient synthesis. These natural products and synthetic compounds have shown numerous interesting biological activities with clinical potentials against various diseases. This review aims to highlight the recent evidence of chalcone as a privileged scaffold in medicinal chemistry. Multiple aspects of chalcone will be summarized herein, including the isolation of novel chalcone derivatives, the development of new synthetic methodologies, the evaluation of their biological properties, and the exploration of the mechanisms of action as well as target identification. This review is expected to be a comprehensive, authoritative, and critical review of the chalcone template to the chemistry community.

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“…The desired sulfonic acids (7) were synthesized in high yields (87−97%) and with excellent enantioselectivity (84−99%) (Scheme 14). 176 5.1.2. Aminohalogenations of Chalcones.…”

Section: Michael Additionmentioning

confidence: 99%

Chalcone: A Privileged Structure in Medicinal Chemistry

et al. 2017

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“…118 Additionally, it was reported that sulfonic acids 105 generated utilizing an appropriate aminothiourea bifunctional catalyst with excellent enantioselectivity (84-99%). 119 Scheme 26 Oxidation cyclization products from 2'-hydroxychalcone.…”

Section: One-pot Synthesis Of Chalconesmentioning

confidence: 99%

Synthesis, reactions and application of chalcones: a systematic review

2023

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“…16,18,19,39,45 As far as we know, synthesis of sulfonate gemini surfactants using natural linoleic acid as building blocks is rarely reported. Inspired by the reported work on organocatalyzed addition of NaHSO 3 to α,β-unsaturated alkenes by employing organic base catalysis [46][47][48][49][50] as well as our previous work on sulfonation of alkyl oleate with NaHSO 3 catalyzed by the TBPB/iron (III) chloride (FeCl 3 ) system, 32 we initiated our investigation on the synthesis of sulfonate gemini surfactants through the addition of NaHSO 3 to alkyl linoleate so as to find appropriate conditions using MLO as a model substrate Notably, SMLD was detected as the only product with varying the reaction time (Figure S7). Hence, 20 h was chosen as the optimal reaction time.…”

Section: Optimization Of Sulfonation Reaction Conditionsmentioning

confidence: 99%

Renewable dissymmetric sulfonate gemini surfactants from addition of sodium hydrogensulfite to alkyl linoleate

Jia

et al. 2022

AIChE Journal

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A new series of bio‐based sulfonate gemini surfactants was synthesized through esterification of renewable linoleic acid with various alcohols and subsequent sulfonation with readily available sodium hydrogensulfite (NaHSO3). Organocatalytic sulfonation of methyl linoleate with NaHSO3 by the triethylamine and tert‐butyl peroxybenzoate catalyst system was investigated, where a methyl linoleate conversion of 96.4% could be achieved while generating high purity product without tedious purification. Three resulting sodium alkyl linoleate disulfonates (SALDs) have been characterized by Fourier transform infrared, high‐performance liquid chromatography, LC–MS, high‐resolution mass spectrometry (HR–MS), nuclear magnetic resonance techniques, and thermogravimetric analysis. The physicochemical properties and surface properties of the SALDs at various concentrations were investigated. The results showed that the SALDs exhibited low Krafft temperature, high water solubility, foam stability (foam half‐life time could reach 15 min), emulsifying ability (emulsification time of 2.0 g/L is 192 s), and good thermal stability. This study enriches the family of anionic gemini surfactants and provides reference data for facile preparation of gemini surfactants.

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Catalytic Enantioselective Addition of Sodium Bisulfite to Chalcones

Cited by 13 publications

References 37 publications

Chalcone: A Privileged Structure in Medicinal Chemistry

Chalcone: A Privileged Structure in Medicinal Chemistry

Synthesis, reactions and application of chalcones: a systematic review

Renewable dissymmetric sulfonate gemini surfactants from addition of sodium hydrogensulfite to alkyl linoleate

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