Product selectivity in the photoreaction of aryl sulfonates and mesylate of estrone derivatives in sustainable and micellar media: a steady-state investigation

Quindt, Matías I.; Gola, Gabriel; Rodríguez, Cristian; Ramírez, Javier A.; Bonesi, Sergio M.

doi:10.1039/d2nj02989h

Cited by 4 publications

(3 citation statements)

References 80 publications

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“…Therefore, collecting the whole results described before clearly demonstrated that the photo-Fries rearrangement reaction of esters 1 – 5 that takes place from the singlet excited state S 1 and the triplet excited state T 1 is not involved in the photoreaction. Moreover, this photochemical reactivity was also observed for 3-acyl and 3-aryl/alkylsulfonyl estrone derivatives where the singlet state was demonstrated to be the photo reactive excited state of this kind of compounds …”

Section: Resultsmentioning

confidence: 62%

“…Lumiestrone 10 was also detected in the reaction mixtures of esters 1 – 4 in very low yields when the photoreaction was carried out in both solvents with the exception of the cases of esters 1 and 4 in methanol where compound 10 was formed in 22 and 30% yields, respectively. Epimerization of the methyl group at C-13 of estrone 6 accounts for the formation of lumiestrone because a Norrish Type I is involved during the photochemical reaction and competes with the photo-Fries rearrangement process. , …”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, these two estrogens are useful building blocks leading to the preparation of derivatives with potential application in the treatment of medical conditions and diseases . In this context, photochemical approaches toward the preparation of steroids and natural products have been successfully achieved. , On the other hand, the photochemical behavior of steroids has also been investigated deeply and, in the case of some estrone derivatives, the photo-Fries rearrangement reaction have been applied from a preparative viewpoint successfully. − …”

Section: Introductionmentioning

confidence: 99%

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Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives

Quindt,

Gola,

Ramirez

et al. 2023

J. Org. Chem.

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A protocol involving the irradiation of some 3-(2-alkenyl)estrone and 3-(2-alkenyl)-17-norestrone derivatives under a nitrogen atmosphere in organic solvents (both hexane and MeOH) followed by base-mediated intramolecular oxa-Michael cyclization reaction was investigated under steady-state conditions. The solvent effect and nature of the acyl group on the preparative photoreaction were studied and the multiplicity of the excited state was also demonstrated. The ortho-regioisomers were obtained in modest to good yields. Intramolecular based-mediate cyclization reaction of these synthons led to the formation of a set of novel substituted 4-chromanone moieties fused to estrone (and 17-norestrone) in good yields. This two-step sequential procedure involving a photochemical/intramolecular thermal cyclization strategy will be useful for the preparation of wide heterocyclic-fused-steroid compounds.

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Section: Resultsmentioning

confidence: 62%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives

Quindt,

Gola,

Ramirez

et al. 2023

J. Org. Chem.

Self Cite

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Photoinduced One‐Electron Oxidation of Estrone Derivatives: A Combined Steady‐State and Time‐Resolved Spectroscopy Investigation

Quindt,

Protti,

Merli

et al. 2023

ChemPhotoChem

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A detailed investigation of the photophysics and of the redox properties of a set of selected estrone carboxylate and sulfonate esters was carried out by means of steady‐state and time‐resolved spectroscopies. The observed dual fluorescence was assigned to an efficient intramolecular energy transfer from the aromatic moiety to the carbonyl group. On the other hand, the photoinduced monoelectronic oxidation of R‐OX in the presence of persulphate anion is followed by mesolytic fragmentation of the so generated radical cation into the corresponding phenoxyl radical with rate constant values (kfrag) of 104 – 105 s‐1, that depend on the X‐O bond dissociation energy values.

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Effect of Sustainable and Confined Media on the Photoinduced [6π]‐Electrocyclization Reaction of Diphenyl and N‐Methyldiphenylamines.

Salum,

Protti,

Mella

et al. 2024

ChemPhotoChem

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A systematic investigation of the photoinduced [6π]‐electrocyclization reaction of diphenylamine and N‐methyldiphenylamine has been carried out under steady‐state and time‐resolved conditions in homogeneous (cyclohexane, acetonitrile and methanol) and micellar solutions (sodium dodecyl sulfate ‐SDS, cetyltrimethylammonium chloride‐CTAC and polyethylene glycol monododecyl ether‐Brij P35). The photolysis of such compounds in both homogeneous and micro‐heterogeneous media afforded the corresponding carbazoles in almost quantitative yield under oxidative conditions. Furthermore, the relative rate of formation of the photoproducts increases when moving from homogeneous media to micellar solution, due to the environmental confined and hydrophobic micellar core as highlighted by 1D and 2D NMR (NOESY and DOSY) spectroscopic analyses.

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Product selectivity in the photoreaction of aryl sulfonates and mesylate of estrone derivatives in sustainable and micellar media: a steady-state investigation

Abstract: Preparative and mechanistic studies on the photochemical reaction of a series of aryl sulfonates and mesylate of estrone and 17-norestrone derivatives in confined and sustainable micellar environment under steady-state conditions...

Cited by 4 publications

References 80 publications

Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives

Light-Driven Two-Step Preparation of 4-Chromanone Fused to Estrone Derivatives

Photoinduced One‐Electron Oxidation of Estrone Derivatives: A Combined Steady‐State and Time‐Resolved Spectroscopy Investigation

Effect of Sustainable and Confined Media on the Photoinduced [6π]‐Electrocyclization Reaction of Diphenyl and N‐Methyldiphenylamines.

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