Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones

Iguchi, Daniela; Erra‐Balsells, Rosa; Bonesi, Sergio M.

doi:10.1016/j.tetlet.2014.06.081

Cited by 15 publications

(10 citation statements)

References 26 publications

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“…The preparation of griseofulvin (30), daunomycinone (31) and flavonoids (32) has successfully employed the photo‐Fries rearrangement reaction; however, most of the studies have been devoted to elucidating the mechanism of the reaction rather than its application as a synthetic methodology. In addition, we have also contributed to show how important is the application of the photo‐Fries rearrangement reaction in the preparation of 2,2‐dimethyl‐4‐chromanone derivatives (33,34) and carbazole derivatives (35,36). Recently, we were able to show the selectivity and the effect of surfactant micelles on the photo‐Fries reaction of an assortment of substituted acetamides (37) as well as substituted aryl benzoates (38) and also, the photochemical behavior of 3‐aryloxy estrone derivatives in solution (39).…”

Section: Introductionmentioning

confidence: 99%

Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies

Quindt

Gola

Ramírez

et al. 2020

Photochem & Photobiology

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Direct irradiation of estrone aryl and methyl sulfonates in different organic solvents under nitrogen atmosphere was investigated under steady‐state conditions. The estrone derivatives reacted efficiently through the photo‐Fries rearrangement reaction involving [1;3]‐sulfonyl migration providing the ortho‐sulfonyl estrone derivatives and estrone as the photoproducts. In addition, estrone and 2‐arylsulfonyl estrone derivatives were epimerized involving a Norrish Type‐I reaction. Chemical quenching and photosensitization experiments on the photoreaction have been also carried out to establish the photoreactive excited state. Likewise, the solvent effect and the nature of the sulfonyl group on the photoreactions have been also studied.

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Section: Introductionmentioning

confidence: 99%

Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies

Quindt

Gola

Ramírez

et al. 2020

Photochem & Photobiology

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“…With the persistent efforts of many chemists, adequate evolutions have been achieved on the synthesis of both types of essential molecular scaffolds 2f–i. 3a,e,f, 9, 10 Nevertheless, the development of efficient and straightforward methods in a simple operation and under mild conditions is still fueled by the strong and growing aspiration for such processes in most areas of chemical synthesis.…”

Section: Introductionmentioning

confidence: 99%

Convenient and Highly Efficient Routes to 2 H‐Chromene and 4‐Chromanone Derivatives: Iodine‐Promoted and p‐Toluenesulfonic Acid Catalyzed Cascade Cyclizations of Propynols

Qiu

Song

et al. 2015

Chemistry A European J

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A convenient strategy is presented for the easy preparation of a series of 2 H-chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4-chromanones can be synthesized through a p-toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99 %). Our developed reaction systems are proven to have good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. These systems also provide a new synthetic strategy for two types of important flavonoid skeleton without using costly and toxic metal catalysts. Additionally, the resulting halides could be further exploited in subsequent palladium-catalyzed coupling reactions, so these compounds could act as potential intermediates for the construction of some valuable drug molecules.

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“…[3][4][5][6][12][13][14] Further accounts have detailed the use of stoichiometric mercury(II) on aryl propargyl ethers, 15 the addition of cuprates to chromones, 16 the treatment of phenols and 3,3-dimethylacrylic acid with excess phosphorus oxychloride/zinc chloride, 17,18 the reaction of carboxylic acids with o-(trimethylsilyl)aryl triflates promoted by cesium fluoride 19 and a one-pot, base-mediated photo-Fries-oxa-Michael reaction. 20 The current project originated from efforts to extend the Friedel-Crafts ring closure of phenyl 3,3-dimethylacrylate (1a, X = H) to other phenol-derived acrylate esters. Cyclization of 1a is reported to give 4,4-dimethyl-2-chromanone (2a) in >70% yield using 1.7 equiv of aluminum chloride in dichloromethane, 21 and we have successfully employed this procedure to access drug precursors for one of our projects.…”

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confidence: 99%

Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones

Meraz

Gnanasekaran

Thing

et al. 2016

Tetrahedron Letters

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An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20 mol% bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25-90% yields of products are realized following chromatography. A range of substrates is included (14 substrates for each acid) to help define the scope of the process. Additional experiments are reported, which confirm that the sequence of events involves (1) esterification, (2) Fries rearrangement and (3) oxa-Michael ring closure.

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Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones

Cited by 15 publications

References 26 publications

Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies

Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies

Convenient and Highly Efficient Routes to 2 H‐Chromene and 4‐Chromanone Derivatives: Iodine‐Promoted and p‐Toluenesulfonic Acid Catalyzed Cascade Cyclizations of Propynols

Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones

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