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Abstract:

The photochemistry of two 2-acyloxycarbazoles, 2-acetyl- and 2-benzoyloxycarbazole, in different solvents has been studied. Irradiation of the 2-acyloxycarbazoles in organic media at 254 or 313 nm yields the [1,3]-migrated photoproducts, 1-acyl-2-hydroxycarbazole, 3-acyl-2-hydroxycarbazole and 2-hydroxycarbazole. The effects of the solvent, the atmosphere and the intensity of the light source on the photochemistry of 2-acyloxycarbazole have been studied. Laser flash photolysis as well as photosensitization experiments were performed in order to determine the photoreactive excited state. Electronic spectra (absorption, fluorescence and phosphorescence emission spectra) of the 2-acyloxycarbazoles have been recorded in homogeneous media at 298 K and in solid matrices at 77 K. The dynamic properties of the lowest singlet excited state in terms of fluorescence lifetime and fluorescence quantum yield have been measured in different organic solvents at room temperature. The photo-Fries rearrangement as a mild and clean one-pot reaction for the preparation of an advanced intermediate precursor in the total synthesis of carbazole alkaloids is described. © The Royal Society of Chemistry and Owner Societies 2004.

Registro:

Documento: Artículo
Título:Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids
Autor:Bonesi, S.M.; Crevatín, L.K.; Erra-Balsells, R.
Filiación:CIHIDECAR-CONICET, Departamento de Quimica Organica, Universidad de Buenos Aires, Pabellón II, 3er Piso, 1428 Buenos Aires, Argentina
Palabras clave:2 acetyloxycarbazole; 2 benzoyloxycarbazole; alkaloid derivative; carbazole derivative; girinimbine; mahanimbinin; Murraya koenigii extract; murrayacine; murrayanine; plant extract; unclassified drug; absorption spectroscopy; article; column chromatography; controlled study; drug structure; drug synthesis; fluorescence analysis; Murraya; Murraya koenigii; nonhuman; phosphorescence; photochemistry; photolysis; photoreactivity; photosensitization; priority journal; quantum yield; room temperature
Año:2004
Volumen:3
Número:4
Página de inicio:381
Página de fin:388
DOI: http://dx.doi.org/10.1039/b315691e
Título revista:Photochemical and Photobiological Sciences
Título revista abreviado:Photochem. Photobiol. Sci.
ISSN:1474905X
CODEN:PPSHC
CAS:girinimbine, 23095-44-5
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v3_n4_p381_Bonesi

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Citas:

---------- APA ----------
Bonesi, S.M., Crevatín, L.K. & Erra-Balsells, R. (2004) . Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids. Photochemical and Photobiological Sciences, 3(4), 381-388.
http://dx.doi.org/10.1039/b315691e
---------- CHICAGO ----------
Bonesi, S.M., Crevatín, L.K., Erra-Balsells, R. "Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids" . Photochemical and Photobiological Sciences 3, no. 4 (2004) : 381-388.
http://dx.doi.org/10.1039/b315691e
---------- MLA ----------
Bonesi, S.M., Crevatín, L.K., Erra-Balsells, R. "Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids" . Photochemical and Photobiological Sciences, vol. 3, no. 4, 2004, pp. 381-388.
http://dx.doi.org/10.1039/b315691e
---------- VANCOUVER ----------
Bonesi, S.M., Crevatín, L.K., Erra-Balsells, R. Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids. Photochem. Photobiol. Sci. 2004;3(4):381-388.
http://dx.doi.org/10.1039/b315691e