Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids
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-hyd...
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2004
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v3_n4_p381_Bonesi http://hdl.handle.net/20.500.12110/paper_1474905X_v3_n4_p381_Bonesi |
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paper:paper_1474905X_v3_n4_p381_Bonesi2023-06-08T16:17:45Z Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids 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 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. 2004 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v3_n4_p381_Bonesi http://hdl.handle.net/20.500.12110/paper_1474905X_v3_n4_p381_Bonesi |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids |
| topic_facet |
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 |
| description |
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. |
| title |
Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids |
| title_short |
Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids |
| title_full |
Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids |
| title_fullStr |
Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids |
| title_full_unstemmed |
Photochemistry of 2-acyloxycarbazoles. A potential tool in the synthesis of carbazole alkaloids |
| title_sort |
photochemistry of 2-acyloxycarbazoles. a potential tool in the synthesis of carbazole alkaloids |
| publishDate |
2004 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1474905X_v3_n4_p381_Bonesi http://hdl.handle.net/20.500.12110/paper_1474905X_v3_n4_p381_Bonesi |
| _version_ |
1768544793151930368 |