Cleavage of Alkyl o-Hydroxyphenyl Ethers

Lange, Robert

doi:10.1021/jo01053a030

Cited by 76 publications

(48 citation statements)

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“…Cleavage of the methylenedioxy ring of nitrosafrol took place during the conversion into the catechol 4 (57.4% yield) using the AlCl 3 /CH 2 Cl 2 /H 2 O method [12][13][14][15] . In the 1 H NMR spectrum, the absence of the methylenedioxy singlet between 5.90-6.05 ppm confirmed the presence of catechol coupled with a broad signal at d=8.99 (brs, 2H).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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Safrole from sassafras oil (Ocotea pretiosa Mez., Lauraceae), is an abundant natural product showing interesting functionality and chemical structure. Starting from safrole, nine derivatives were prepared and assessed for antiproliferative effect using different human cell lines. The in vitro growth inhibition assay was based on the sulphorhodamine dye to quantify cell viability. Some safrole derivatives, (2E)-3-(3',4'-methylenedioxi)phenyl acrylaldehyde (3) and 4-allyl-5-nitrobenzene-1,2-diol (4) presented better antiproliferative effect than the parent compound on two breast cancer cell lines (MCF-7 and MDA-MB-231) and one human colorectal cancer cell line (DLD-1) with IC 50 values of 55.0 + 7.11 µM, 37.5 + 2.65 µM and 44.0 + 6.92 µM, respectively, without toxicity towards dermal human fibroblast (DHF cells).

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Section: Resultsmentioning

confidence: 99%

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Espinoza

Madrid

Liber

et al. 2010

J. Chil. Chem. Soc.

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“…3-Bromo-4,5-dihydroxybenzaldehyde (3): [16] Anhydrous aluminum chloride (3.2 g, 23.8 mmol) was suspended in a solution of 5-bromovanillin (5.0 g, 21.6 mmol) in CH 2 Cl 2 (50 mL). While cooling to maintain the temperature at 30-35 8C, pyridine (7.7 mL, 95.2 mmol) was added slowly.…”

Section: Methodsmentioning

confidence: 99%

“…[15] Results and Discussion Synthesis: The sequence of reactions leading to target compounds began with commercially available 5-bromovanillin. Thus, cleavage of the methyl ether group of 5-bromovanillin by using anhydrous AlCl 3 in the presence of pyridine furnished catechol 3 [16] in 77 % yield. Next, protection of the hydroxy groups of 3 as their tert-butyldiphenylsilyl (TBDPS) derivatives was accomplished by using TBDPSCl and anhydrous 1,8-diazabicycloA C H T U N G T R E N N U N G [5.4.0]undec-7-ene (DBU) in a mixture of THF and N,N-dimethylformamide (DMF), affording compound 4 in 58 % yield along with the monoprotected product 5 in 7 % yield.…”

Section: Introductionmentioning

confidence: 99%

Catechol Derivatives as Fluorescent Chemosensors for Wide‐Range pH Detection

Evangelio

Hernando

Imaz

et al. 2008

Chemistry A European J

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The synthesis and characterization of a new family of catechol derivatives designed to behave as fluorescent chemosensors for wide-range pH detection has been described. These compounds were prepared by covalently coupling a catechol unit with other aromatic rings, thus obtaining pi-delocalized systems with both pH-responsive groups and fluorescent behavior. In the case of a pyridine-catechol derivative, this leads to up to three different protonation states with distinct optical properties in organic media, as corroborated by density functional theory calculations. By applying dual-wavelength detection techniques, this compound shows complementary "off-on-off" and "on-off-on" emission profiles upon pH variation, a behavior that can be exploited to perform acidity detection over a broad pH range.

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“…Catalytic oxidation of organic halides to aldehydes and ketones with H 5 IO 6 in ionic liquid has been also developed [22]. Another synthetic route is the vanillin demethylation with pyridine and AlCl 3 [23]. These routes make all use of harmful reagents or environmentally unsafe heavy metals.…”

Section: Introductionmentioning

confidence: 99%

Photocatalytic green synthesis of piperonal in aqueous TiO2 suspension

Bellardita

Loddo

Palmisano

et al. 2014

Applied Catalysis B: Environmental

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a b s t r a c tPiperonal (heliotropine or 3,4-methylenedioxybenzaldehyde) has been synthesized by oxidizing piperonyl alcohol in aqueous UV-irradiated TiO 2 suspensions. This compound was identified by GC-MS chromatography, 1 H NMR and melting point determination. The other products of the photoprocess were 1,3-bis(3,4-(methylenedioxy)benzyl) ether (found in traces) and CO 2 , derived from the parallel pathway of photo-mineralization. Commercial and home-prepared TiO 2 samples have been tested and the best selectivity (ca. 35%) was obtained by using the home-prepared ones. The reported green process allows to obtain an added value product (piperonal), upon partial oxidation of a cheap reagent.

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Cleavage of Alkyl o-Hydroxyphenyl Ethers

Cited by 76 publications

References 0 publications

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Synthesis of Nine Safrole Derivatives and Their Antiproliferative Activity Towards Human Cancer Cells

Catechol Derivatives as Fluorescent Chemosensors for Wide‐Range pH Detection

Photocatalytic green synthesis of piperonal in aqueous TiO2 suspension

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