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

2012
journal article
article
cris.lastimport.wos2024-04-09T23:14:04Z
dc.abstract.enAn 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). $^{1}\textrm{H}$ NMR and X-ray crystal structure analyses of 1-aryl-3-(alkylaminophenylmethylidene)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 $^{1}\textrm{H}$ 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 $\pm$ 0.51 $\mu$M.pl
dc.affiliationWydział Chemii : Zakład Krystalochemii i Krystalofizykipl
dc.affiliationWydział Biochemii, Biofizyki i Biotechnologii : Zakład Biochemii Analitycznejpl
dc.affiliationWydział Chemii : Zakład Chemii Organicznejpl
dc.contributor.authorOstrowska, Katarzyna - 131207 pl
dc.contributor.authorPiegza, Edytapl
dc.contributor.authorRąpała-Kozik, Maria - 131641 pl
dc.contributor.authorStadnicka, Katarzyna - 132048 pl
dc.date.accessioned2015-09-07T11:00:24Z
dc.date.available2015-09-07T11:00:24Z
dc.date.issued2012pl
dc.description.number19pl
dc.description.physical3636-3646pl
dc.description.points30pl
dc.description.volume2012pl
dc.identifier.doi10.1002/ejoc.201200211pl
dc.identifier.eissn1099-0690pl
dc.identifier.issn1434-193Xpl
dc.identifier.urihttp://ruj.uj.edu.pl/xmlui/handle/item/15354
dc.languageengpl
dc.language.containerengpl
dc.rightsDodaję tylko opis bibliograficzny*
dc.rights.licencebez licencji
dc.rights.uri*
dc.subject.ennitrogen heterocyclespl
dc.subject.enzincpl
dc.subject.enenaminespl
dc.subject.enE / Z interconversionpl
dc.subject.enfluorescent probespl
dc.subtypeArticlepl
dc.titleEfficient 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)ionpl
dc.title.journalEuropean Journal of Organic Chemistrypl
dc.typeJournalArticlepl
dspace.entity.typePublication
cris.lastimport.wos
2024-04-09T23:14:04Z
dc.abstract.enpl
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). $^{1}\textrm{H}$ NMR and X-ray crystal structure analyses of 1-aryl-3-(alkylaminophenylmethylidene)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 $^{1}\textrm{H}$ 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 $\pm$ 0.51 $\mu$M.
dc.affiliationpl
Wydział Chemii : Zakład Krystalochemii i Krystalofizyki
dc.affiliationpl
Wydział Biochemii, Biofizyki i Biotechnologii : Zakład Biochemii Analitycznej
dc.affiliationpl
Wydział Chemii : Zakład Chemii Organicznej
dc.contributor.authorpl
Ostrowska, Katarzyna - 131207
dc.contributor.authorpl
Piegza, Edyta
dc.contributor.authorpl
Rąpała-Kozik, Maria - 131641
dc.contributor.authorpl
Stadnicka, Katarzyna - 132048
dc.date.accessioned
2015-09-07T11:00:24Z
dc.date.available
2015-09-07T11:00:24Z
dc.date.issuedpl
2012
dc.description.numberpl
19
dc.description.physicalpl
3636-3646
dc.description.pointspl
30
dc.description.volumepl
2012
dc.identifier.doipl
10.1002/ejoc.201200211
dc.identifier.eissnpl
1099-0690
dc.identifier.issnpl
1434-193X
dc.identifier.uri
http://ruj.uj.edu.pl/xmlui/handle/item/15354
dc.languagepl
eng
dc.language.containerpl
eng
dc.rights*
Dodaję tylko opis bibliograficzny
dc.rights.licence
bez licencji
dc.rights.uri*
dc.subject.enpl
nitrogen heterocycles
dc.subject.enpl
zinc
dc.subject.enpl
enamines
dc.subject.enpl
E / Z interconversion
dc.subject.enpl
fluorescent probes
dc.subtypepl
Article
dc.titlepl
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
dc.title.journalpl
European Journal of Organic Chemistry
dc.typepl
JournalArticle
dspace.entity.type
Publication
Affiliations

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