A facile synthesis of α,α′-bis(substituted-benzylidene)-cycloalkanones and substituted-benzylidene heteroaromatics: utility of NaOAc as a catalyst for aldol-type reaction

Rahman, A. F. M. Motiur; Jeong, Byeong‐Seon; Kim, Dong Hyeon; Park, Jung Ki; Lee, Eung Seok; Jahng, Yurngdong

doi:10.1016/j.tet.2007.01.020

Cited by 30 publications

(5 citation statements)

References 48 publications

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“…The reason was probably a very low electrophilicity of the formed phenolate salt of the aldehyde. The condensation reaction was unsuccessful using SOCl 2 in anhydrous EtOH [ 64 ], molecular iodine (I 2 ) in DCM at room temperature [ 65 ], Cu(OTf) 2 in solvent-free conditions at 80 °C [ 66 ], and NaOAc in solvent-free conditions [ 67 ]. Attempts were also made to heat compound 1 with vanillin under microwave irradiation at 120 °C in trifluoroacetic acid, unfortunately also without success.…”

Section: Resultsmentioning

confidence: 99%

Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity

Pawelski

Walewska

Ksiezak

et al. 2021

IJMS

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Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., l-cocaine and l-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed.

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Section: Resultsmentioning

confidence: 99%

Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity

Pawelski

Walewska

Ksiezak

et al. 2021

IJMS

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“…NMR yield 89% (with 1,4-dinitrobenzene as internal standard). The residue was purified using preparative flash chromatograph InterChim PuriFlash in DCM−MeOH binary system (gradient 100% DCM to 10% MeOH in DCM for 30 4-Chloro-2-(pyrrolidin-1-ylmethyl)aniline (3da). Some important general details are described in general procedure A.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…The synthetic procedure was similar to that described by Jahng. 30 A round-bottom flask (250 mL) was charged with deoxyvasicinone from the previous step (6.5 g, 35 mmol, 100 mol %), 4-hydroxy-3,5-dimethoxybenzaldehyde (12.7 g, 70 mmol, 200 mol %), AcONa (573 mg, 7 mmol, 20 mol %), and AcOH (70 mL) under air atmosphere. The reaction mixture was refluxed for 15 h and then stirred for 48 h to get easy to handle precipitate.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

et al. 2020

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A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

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“…Bis-chalcone derivatives (P1 and P2) were synthesized as indicated in the literature by condensation of cyclopentanone with aromatic aldehydes, respectively (Figure 1) (Motiur Rahman, 2007;Yakalı et al, 2019). Synthesis and spectroscopic details of the compounds are given in these literatures (Li et al, 2003;Motiur Rahman et al, 2007).…”

Section: Synthesis Of P1 and P2mentioning

confidence: 99%

Bis-Kalkon Türevlerinin Elektrokimyasal Davranışlarının İncelenmesi

Maşlakcı

Kömür

Biçer³

et al. 2020

Mehmet Akif Ersoy Üniversitesi Fen Bilimleri Enstitüsü Dergisi

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The electrochemical behavior of (2E,5E)-2,5-dibenzylidenecyclopentanone (P1) and (2E,5E)-2,5-bis(4-nitrobenzylidene)cyclopentanone (P2) known as bis-chalcone derivatives was studied by cyclic voltammetry (CV) using an indium tin oxide (ITO) as the working electrode. Repeated cyclic voltammograms measurements exhibited excellent longterm redox stability for bis-chalcone derivatives. The oxidation peak for in the anodic region for the 1st cycle of the P1 appeared at -0.20 V, while the oxidation peak of P2 was observed at -0.47 V. On the other hand, the existence of the electron attracting NO2 group at p-position on the benzene ring in the structure of P2 caused an increase in the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy gap. The surface morphology and structural features of P1 and P2 films coated onto ITO glass substrates were investigated by using scanning electron microscopy (SEM) and energy-dispersive X-ray spectroscopy (EDS). SEM micrographs demonstrated that the P1 and P2 were homogeneously distributed over the ITO surface. After CV measurement, it was observed that the grain size of P2 increased with increasing ITO surface roughness. Moreover, the EDS results confirmed the presence of P1 and P2 on the ITO surface.

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A facile synthesis of α,α′-bis(substituted-benzylidene)-cycloalkanones and substituted-benzylidene heteroaromatics: utility of NaOAc as a catalyst for aldol-type reaction

Cited by 30 publications

References 48 publications

Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity

Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

Bis-Kalkon Türevlerinin Elektrokimyasal Davranışlarının İncelenmesi

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