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Efficient N-alkyl enamination of 3-(thiobenzoyl)pyrrolo[2,3-b]quinoxalin-2-one, E/Z isomerisation of the reaction products and potential fluorescent sensors for zinc(II)ion
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Efficient N-alkyl enamination of 3-(thiobenzoyl)py ...
Bibliographic description
| title: | Efficient N-alkyl enamination of 3-(thiobenzoyl)pyrrolo[2,3-b]quinoxalin-2-one, E/Z isomerisation of the reaction products and potential fluorescent sensors for zinc(II)ion |
| author: | Ostrowska Katarzyna  , Piegza Edyta, Rąpała-Kozik Maria , Stadnicka Katarzyna
|
| Journal title: | European Journal of Organic Chemistry |
| volume: | 2012 |
| issue: | 19 |
| date of publication: | 2012 |
| pages: | 3636-3646 |
| ISSN: |
1434-193X |
| eISSN: |
1099-0690 |
| DOI: | |
| language: | English |
| Journal language: | English |
| abstract in english: | An efficient and rapid procedure for the N -alkyl enamination from thioketones to push–pull ( E / Z )-enamine derivatives is reported. The starting thioketone 2 was obtained by regiose- lective thionation of 3-benzoylpyrrolo[2,3- b ]quinoxalin-2- one ( 1 ) with Lawesson’s reagent (LR). 1 H NMR and X-ray crystal structure analyses of 1-aryl-3-(alkylaminophenyl- methylidene)pyrrolo[2,3- b ]quinoxalin-2-ones 3 – 6 confirmed that the E diastereoisomers predominated. Interconversion of the isolated E form of 3b and 4a into the Z configuration and their E / Z equilibria in [D 6 ]DMSO were studied by tempera- ture-dependent 1 H NMR spectroscopy. The photophysical properties of compounds 1 – 6 are also reported. We found that the non-fluorescent compounds 3a – 6a are chemosensors for the zinc ion. Fluorescent titrations of these sensors with zinc- (II) acetate showed that compound 6a has the best working range of zinc concentrations with K d = 3.77 00 0.51 μ M. |
| keywords in english: | nitrogen heterocycles, zinc, enamines, E / Z interconversion, fluorescent probes |
| departmental parameterization: | 30 |
| affiliation: | Wydział Chemii : Zakład Krystalochemii i Krystalofizyki, Wydział Biochemii, Biofizyki i Biotechnologii : Zakład Biochemii Analitycznej, Wydział Chemii : Zakład Chemii Organicznej |
| type: | journal article |
| subtype: | academic paper |
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