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

doi:10.1002/ejoc.201200211

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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punktacja MNiSW [2012 A]: 30

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:	10.1002/ejoc.201200211
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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