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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)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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dc.contributor.author Ostrowska, Katarzyna [SAP11014190] pl
dc.contributor.author Piegza, Edyta pl
dc.contributor.author Rąpała-Kozik, Maria [SAP11012697] pl
dc.contributor.author Stadnicka, Katarzyna [SAP11004149] pl
dc.date.accessioned 2015-09-07T11:00:24Z
dc.date.available 2015-09-07T11:00:24Z
dc.date.issued 2012 pl
dc.identifier.issn 1434-193X pl
dc.identifier.uri http://ruj.uj.edu.pl/xmlui/handle/item/15354
dc.language eng pl
dc.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 pl
dc.type JournalArticle pl
dc.description.physical 3636-3646 pl
dc.abstract.en 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. pl
dc.subject.en nitrogen heterocycles pl
dc.subject.en zinc pl
dc.subject.en enamines pl
dc.subject.en E / Z interconversion pl
dc.subject.en fluorescent probes pl
dc.description.volume 2012 pl
dc.description.number 19 pl
dc.description.points 30 pl
dc.identifier.doi 10.1002/ejoc.201200211 pl
dc.identifier.eissn 1099-0690 pl
dc.title.journal European Journal of Organic Chemistry pl
dc.language.container eng pl
dc.affiliation Wydział Chemii : Zakład Krystalochemii i Krystalofizyki pl
dc.affiliation Wydział Biochemii, Biofizyki i Biotechnologii : Zakład Biochemii Analitycznej pl
dc.affiliation Wydział Chemii : Zakład Chemii Organicznej pl
dc.subtype Article pl
dc.rights.original bez licencji pl
.pointsMNiSW [2012 A]: 30


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