Photochemical ring expansion of 4-azidouracil : a route to 5H-1,3,5-triazepin-2,4-dione in the nucleoside series
| Autor: | Michèle Cesario, Frédéric Peyrane, Pascale Clivio |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2006 |
| Předmět: |
Reaction mechanism
Azides Photochemistry Pyridines 010402 general chemistry Ring (chemistry) 01 natural sciences Chemical synthesis chemistry.chemical_compound Nucleophile Uracil Carbodiimide Diketone 010405 organic chemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Photodissociation Water Nucleosides Azepines 0104 chemical sciences Carbodiimides Solvents Nucleoside |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2006, 71(4), pp.1742-1745. ⟨10.1021/jo0524066⟩ |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/jo0524066⟩ |
| Popis: | Under aqueous conditions, 4-azidouracil/tetrazolo[1,5-c]pyrimidin-5(6H)-one nucleosides undergo a very efficient photochemical nitrogen elimination and ring expansion to 1,3,5-triazepin-2,4-dione nucleosides whose structure has been confirmed by X-ray crystallography. In contrast, when the photolysis was attempted under anhydrous conditions in the presence of a nucleophile, a ring contraction reaction occurred, affording 2-oxoimidazolone nucleosides. A mechanism to account for the formation of ring expansion and contraction reactions and involving a carbodiimide intermediate is proposed which is reminiscent of the known photochemical behavior of 2-azidopyridines/tetrazolo[1,5-a]pyridines. |
| Databáze: | OpenAIRE |
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