General Rearrangement of 3-Substituted Chromones. Rearrangement to 1-Benzoxepins and 4-Chromanones

Klutchko, S.; Strandtmann, M. Von

doi:10.1055/s-1977-24280

Cited by 18 publications

(13 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Cyclization of Ethyl 2-(2-Acet~yl-3-hydroxyphenox)i)acetate (5) with Sodium Ethoxide in Ethanol. T h e compound 5' (23.8 g, 0.1 mol), dissolved in 600 mI, of ethanol containing 2.3 g of reacted sodium, was stirred overnight a t room temperature.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

A synthesis of 6-hydroxy-1-benzoxepin-3,5(2H,4H)-dione

Wasson¹,

Hamel²,

Rooney³

1977

J. Org. Chem.

View full text Add to dashboard Cite

l u t i o n o f 4. T h e yellow solution formed this way was then transferred under d r y nitrogen i n t o a precooled NMR tube.The Thermal Rearrangement of 4 to Bicycle[ 5.l.Oloctadienyliron Tricarbonyl Cation 3. W h e n a solution of 4 was allowed t o w a r m up t o -60 "C, 'H NMR signals due to i o n 4 completely disappeared a n d were replaced by those o f 3 formed quantitatively. I3C NMR Spectroscopic Study.T h e 13C NMR spectra were obtained using a V a r i a n XL-100-15 NMR spectrometer equipped w i t h FT accessory, spin decoupler, a n d a variable temperature probe. A Varian 620L computer was used t o accumulate data. An external lock (fluorobenzene) was used a n d a l l chemical shifts are referred t o t h e 13C signal o f the enriched ( 5 ) Me4Si capillary.

show abstract

Section: Methodsmentioning

confidence: 99%

“…Cyclization of Ethyl 2-(2-Acetyl-:~-hydroxyphcnoxy)acetate ( 5 ) with Sodium Ethoxide in Toluene. The compound 5 (476.4 mg. (57.6%) of 4 (C,jH(j-petroleum ether), identical to the sample described in the preceding experiment.…”

Section: Methodsmentioning

confidence: 99%

A synthesis of 6-hydroxy-1-benzoxepin-3,5(2H,4H)-dione

Wasson¹,

Hamel²,

Rooney³

1977

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…Flow cytometry was used to assess apoptosis. The detection of apoptotic and necrotic cells was carried out by dual staining with FITC‐conjugated annexin V and propidium iodide (PI) (Roche Diagnostics, Mannheim, Germany), as described previously 24. After 22 h of drug treatment, cells were washed in cold PBS and incubated with 50 µL staining solution containing 1 µL annexin V‐FITC.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Bischromone Derivatives with Antiproliferative Activity

Szulawska-Mroczek

Szumilak

Szczesio

et al. 2012

Archiv der Pharmazie

View full text Add to dashboard Cite

The synthesis of new bischromone derivatives (4a-c and 5a-c) as potential anticancer drugs is described. The difference in the reactivity between 4-oxo-4H-chromene-3-carboxylic acid 2 (or its methyl ester 3) and 4-oxo-4H-chromene-3-carbonyl chloride 1 with three different polyamines: 3,3'-diamino-N-methyldipropylamine (a), 1,4-bis(3-aminopropyl)piperazine (b), 4,9-dioxa-1,12-dodecanediamine (c) resulted in the formation of two different groups of products, compounds 4a-c and 5a-c, designed in agreement with the bisintercalators' structural requirements. The transformation of 4-oxo-4H-chromene-3-carboxylic acid into 2H-chromene-2,4(3H)-diones (5) was confirmed by the NMR and XRD experiments. Compounds 4a and 5a were evaluated in vitro in the highly aggressive melanoma cell line A375. An enhanced induction of apoptosis and cell cycle arrest clearly revealed that compound 5a was more potent than 4a. Compound 5a was also more active in diminishing the adhesive potential of melanoma cells. Current studies support the notion that small changes in the three-dimensional structure of molecules might have a substantial impact on their biological activity.

show abstract

“…It is very difficult to pintpoint whether an initial step of the reaction is C-2 or CHO attack of the nucleophile because of "chemical symmetry" of these reaction centers. Unfortunately none of the published methods for the preparation of 3-formylchromones is suitable for incorporation of the specific labeling [3][4][5][6][7][8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Transformation of 4‐oxo‐4H‐[1]‐benzopyran‐3‐carboxaldehydes into pyrazolo[3,4‐B]pyridines

Stankovičová¹,

Gáplovský²,

Lácová³

et al. 2006

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

Reaction of 6-methyl-4-oxo-4H-[1]-benzopyran-3-carboxaldehyde 1 with 5-amino-3-methyl-1-phenylpyrazole 2 in alcoholic reaction media in the presence of 4-toluenesulfonic acid as catalyst afforded 5-(2-hydroxy-5-methylbenzoyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine 3 and 2-methoxy-6-methyl-3-(3-methyl-1-phenylpyrazol-5-ylaminomethylene)chroman-4-one 7. We explain the mechanism of formation of both products on the basis of kinetic study of individual reaction steps.

show abstract

General Rearrangement of 3-Substituted Chromones. Rearrangement to 1-Benzoxepins and 4-Chromanones

Cited by 18 publications

References 0 publications

A synthesis of 6-hydroxy-1-benzoxepin-3,5(2H,4H)-dione

A synthesis of 6-hydroxy-1-benzoxepin-3,5(2H,4H)-dione

Synthesis and Biological Evaluation of New Bischromone Derivatives with Antiproliferative Activity

Transformation of 4‐oxo‐4H‐[1]‐benzopyran‐3‐carboxaldehydes into pyrazolo[3,4‐B]pyridines

Contact Info

Product

Resources

About