Copper-catalyzed oxidative esterification of ortho-formyl phenols without affecting labile formyl group

Zheng, Yong; Song, Wenli; Liu, Xuan

doi:10.1016/j.tetlet.2015.06.024

Cited by 12 publications

(5 citation statements)

References 63 publications

(3 reference statements)

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“…The organic phase was dried with Na 2 SO 4 and concentrated under reduced pressure. [ 61 ] The oily product was isolated with Et 2 O.…”

Section: Methodsmentioning

confidence: 99%

“…Yield: 84%, colorless oil. [ 61 ] IR υ max (cm −1 ): 3065, 3036 (aromatic C–H), 2865, 2753 (aldehyde C–H), 1737 (ester C═O), 1693 (HC═O), 1604 (C═C). 1 H NMR (400 MHz, DMSO‐ d 6 , ppm): δ 10.19 (s, 1H, –CH═O), 8.26–8.23 (m, 2H, Ar–H), 7.99 (dd, J = 7.6, 1.2 Hz, 1H, Ar–H), 7.78–7.71 (m, 2H, Ar–H), 7.60 (t, J = 7.8 Hz, 2H, Ar–H), 7.51 (d, J = 7.2 Hz, 1H, Ar–H), 7.47 (d, J = 8.0 Hz, 1H, Ar–H).…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors

Çakmak

Başaran

Şentürk

2022

Archiv der Pharmazie

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In this study, a series of novel Schiff base derivatives containing a pyrazolone ring (2a-e) were designed, successfully synthesized for the first time, and characterized by elemental analysis and some spectroscopic methods. These compounds were tested for their inhibitory activities on acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and the human carbonic anhydrase isoenzymes I and II (hCA I and II). All synthesized molecules indicated significant inhibition effects with IC 50 values ranging from 14.15 to 107.62 nM against these enzymes. Compound 2d showed the most potent inhibitory activity among the tested molecules toward AChE and BChE (IC 50 = 15.07 and 14.15 nM) compared to the standard drug neostigmine. We determined that the IC 50 values of the tested molecules ranged between 16.86 and 57.96 nM for hCA I and 15.24-46.21 nM for hCA II. As a consequence, we may say that some of the Schiff base derivatives may be used as potential drug candidates in later studies.

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“…The organic phase was dried with Na 2 SO 4 and concentrated under reduced pressure. [ 61 ] The oily product was isolated with Et 2 O.…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors

Çakmak

Başaran

Şentürk

2022

Archiv der Pharmazie

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show abstract

“…The reaction of 3‐nitrobenzaldehyde with tetraethyl orthosilicate resulted in the formation of the product 3e (Figure S8) in moderate yield (Table , entry 6). As there are only few reports for the synthesis of aryl esters from aldehydes, we decided to apply our system for the synthesis of aryl esters. For this aim, we used phenol derivatives as the coupling partners (Table , entries 7–11).…”

Section: Introductionmentioning

confidence: 99%

Metal‐free aerobic oxidative esterification of aromatic aldehydes promoted by potassium fluoride (KF)

Soltani

Ghaderi

2019

J Chinese Chemical Soc

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We investigated the oxidative esterification of aldehydes with alcohols/phenols to produce a range of esters. In this approach, we conducted the reaction under metal‐free conditions at room temperature. The reactions were promoted by potassium fluoride (KF) as the additive, resulting in the desired product in good to high yields. This procedure was found to be effective for the production of aryl esters, which are challenging in most of the available reports. It is vital for this procedure not to exclude air as the source of oxygen.

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“…Extending the catalyst quantity to 7 mol% or 10 mol% was not needed, as the yield of 2-(benzo[d]thiazol-2-yl)phenyl benzoate was not augmented markedly (entries 17 and 18, Table 1). It should be noted that 10 mol% catalyst was previously employed for similar transformations, 11,30 while the cross dehydrogenative coupling with dialkylformamides reacquired 5 mol% catalyst.…”

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confidence: 99%

“…Indeed, tert-butyl hydroperoxide was also the oxidant of choice in previous works. 10,11,30 Having these results, we also explored the inuence of oxidant concentration on the transformation (entries 25-29, Table 1). The reaction could not proceed without an oxidant, and no trace quantity of the expected product was detected aer 24 h (entry 25, Table 1).…”

mentioning

confidence: 99%

Superparamagnetic nanoparticles as a recyclable catalyst: a new access to phenol esters via cross dehydrogenative coupling reactions

Nguyen

Dang

et al. 2017

RSC Adv.

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CuFe 2 O 4 superparamagnetic nanoparticles were utilized as a recyclable heterogeneous catalyst for the direct synthesis of chemical structures containing both phenol ester and benzothiazole moieties via cross dehydrogenative coupling reactions. Several substrates were reactive towards the transformation in the presence of the nano catalyst, including benzaldehyde, benzyl alcohol, dibenzyl ether, 2-oxo-2-phenylacetaldehyde, and 2-iodo-1-phenylethanone. This nano catalyst displayed higher catalytic efficiency than many homogeneous and heterogeneous catalysts. The nano CuFe 2 O 4 was easily isolated by using a magnet, and reutilize numerous times without a remarkable deterioration in catalytic performance. To our best knowledge, these reactions were not previously reported in the literature.

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Copper-catalyzed oxidative esterification of ortho-formyl phenols without affecting labile formyl group

Cited by 12 publications

References 63 publications

Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors

Synthesis, characterization, and biological evaluation of some novel Schiff bases as potential metabolic enzyme inhibitors

Metal‐free aerobic oxidative esterification of aromatic aldehydes promoted by potassium fluoride (KF)

Superparamagnetic nanoparticles as a recyclable catalyst: a new access to phenol esters via cross dehydrogenative coupling reactions

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