Synthesis of Hydroxyflavanones from Substituted Acetophenones and Benzaldehydes in the Presence of Silica Gel, Boric Acid and Piperidine

Chan, Wing Lai; Zhang, Wei Han; Lin, Yichao; Szeto, Yau Shan; Lin, Yanwei; Yeung, Chi Ho

doi:10.3987/com-96-7611

Cited by 17 publications

(2 citation statements)

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“…Applications of transition-metal catalysts could efficiently construct flavones, , but they were costly and tough operating conditions were required. Zhang’s group provided an approach for the preparation of flavones: a ring-closure reaction from substituted acetophenones and substituted benzaldehydes in the presence of boric acid and piperidine to generate flavones. This procedure was simple, efficient, and easy to operate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Structure Revision, and Anti-inflammatory Activity Investigation of Putative Blumeatin

Xia

Wu³

et al. 2023

ACS Omega

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Blumeatin, reported herein, bearing two hydroxyl groups at C3′ and C5′ of ring B, is isolated from the traditional Chinese medicine Blumea balsamifera. But the isolation procedure of blumeatin from plants has limitations of prolonged duration and high cost. A procedure featuring Lewis acid-catalyzed ring closure and chiral resolution via Schiff base intermediates is provided here to prepare optically pure blumeatin and its R-isomer efficiently. Furthermore, the structure revision of putative blumeatin based on a logically synthetic procedure and NMR spectroscopic analysis was conducted. The 1D and 2D NMR data analysis unambiguously confirmed our proposal that the reported blumeatin structure has been misassigned as it corresponds to sterubin, which contains two hydroxyl groups at C3′ and C4′ of ring B. Finally, the results of the ear-swelling test exhibited that synthetic (±)-blumeatin and (±)-sterubin had moderate anti-inflammatory activity which was less than that of (−)-sterubin.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Structure Revision, and Anti-inflammatory Activity Investigation of Putative Blumeatin

Xia

Wu³

et al. 2023

ACS Omega

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“…Balan and co-workers have reported that diazinium salts with dihydroxyacetophenone skeleton exhibit antimicrobial activity [5] and the complexes between p-substituted acetophenone and benzoylhydrazones present antifungal activity [6], [7]. Different flavonoids such as chalcones, flavones and flavanones are obtained by reaction between acetophenones and benzaldehydes, in alkaline medium [8], [9]. Substituted acetophenones are used as reagents for the synthesis of several organic reactions.…”

Section: Introductionmentioning

confidence: 99%

Intermolecular interactions, spectroscopic and theoretical investigation of 4-aminoacetophenone

Rocha,

Di Santo,

Ben Altabef

et al. 2019

IJAC

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The molecular structure of 4-aminoacetophenone (PAAP) was determined by DFT calculations using different basis sets. The structural parameters, electronic properties and vibrational wavenumbrers of the optimized geometry have been determined. The vibrational wave-numbers of the fundamental modes of the title compound have been precisely assigned and analyzed and the theoretical results are compared with the experimental vibrations observing a very good correlation. TD-DFT approach was applied to assign the electronic transitions ob-served in the experimental UV-vis spectrum. The molecular electrostatic potential map was used to identify the possible electrophilic and nucleophilic sites. Natural bond orbital (NBO) analysis and atoms in molecules (AIM) approach are applied in order to quantify the relative strength of hydrogen bonding interactions and to account their effect on the stabilities of molecular arrangements. In addition, a detailed exploration of the intermolecular interactions that stabilizes the crystal packing has been performed by using the Hirshfeld surface analysis.Â Â Â

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A review of the syntheses of flavanones, thioflavanones, and azaflavanones from 2'‐substituted chalcones

Lee

2021

Bulletin Korean Chem Soc

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Flavanones have been prepared by the cyclization of 2'-hydroxychalcones using acidic reagents, such as H 2 SO 4 , HX, CF 3 COOH, CH 3 SO 3 H, KF-celite, or SiO 2 . Treatment of 2'-hydroxychalcones with bases, such as LiOH, KOH, NaOAc, K 2 CO 3 , pyridine, Et 3 N, or N-methylimidazole afforded flavanones. The conversion of 2'-hydroxychalcones to flavanones has been conducted using Co(salpr), K 3 Fe (CN) 6 , CuO, or Ni(Tfacac) 2 . Thioflavanones have been prepared by deprotecting and cyclizing S-protected chalcones using AgNO 3 , HBr, CF 3 COOH, or NaOH and by adding NaSH or KCS 2 OEt to 2'-halochalcones and subsequent substitution. Azaflavanones have been prepared by cyclizing 2'-aminochalcones using acidic reagents, such as H 3 PO 4 , HCl, silica chloride, or K-10 clay. Furthermore, treatment of 2'-aminochalcones with Lewis acids, such as ZnCl 2 , SbCl 3 , Yb(OTf) 3 , InCl 3 , TaBr 5 , or CeCl 3 afforded azaflavanones, and chiral azaflavanones were prepared by cyclizing 2'-aminochalcones in the presence of per-6-ABCD, chiral amine, BINOL-phosphoric acid, or thiourea catalyst.

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Synthesis of Hydroxyflavanones from Substituted Acetophenones and Benzaldehydes in the Presence of Silica Gel, Boric Acid and Piperidine

Cited by 17 publications

References 0 publications

Synthesis, Structure Revision, and Anti-inflammatory Activity Investigation of Putative Blumeatin

Synthesis, Structure Revision, and Anti-inflammatory Activity Investigation of Putative Blumeatin

Intermolecular interactions, spectroscopic and theoretical investigation of 4-aminoacetophenone

A review of the syntheses of flavanones, thioflavanones, and azaflavanones from 2'‐substituted chalcones

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