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Regiospecific three-component access to fluorescent 2,4-disubstituted quinolines via one-pot coupling-addition-cyclocondensation-sulfur extrusion sequence

2,4-Di- and 2,4,7-trisubstituted quinolines are readily synthesized in a regioselective fashion from acyl chlorides, terminal alkynes, and 2-aminothiophenols by a consecutive, microwave-assisted one-pot three-component Sonogashira coupling-Michael addition-cyclocondensation sequence and following su...

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Hauptverfasser: Rotzoll, Sven (VerfasserIn) , Willy, Benjamin (VerfasserIn) , Schönhaber, Jan (VerfasserIn) , Rominger, Frank (VerfasserIn) , Müller, Thomas J. J. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 08 June 2010
In: European journal of organic chemistry
Year: 2010, Heft: 18, Pages: 3516-3524
ISSN:1099-0690
DOI:10.1002/ejoc.201000212
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.201000212
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201000212
Volltext
Verfasserangaben:Sven Rotzoll, Benjamin Willy, Jan Schönhaber, Frank Rominger, and Thomas J.J. Müller
Beschreibung
Zusammenfassung:2,4-Di- and 2,4,7-trisubstituted quinolines are readily synthesized in a regioselective fashion from acyl chlorides, terminal alkynes, and 2-aminothiophenols by a consecutive, microwave-assisted one-pot three-component Sonogashira coupling-Michael addition-cyclocondensation sequence and following sulfur extrusion in moderate to good yields. The terminal sulfur extrusion step was studied by DFT computations. The absorption spectra of 2,4-disubstituted quinolines can be rationalized by DFT-ZINDO-CI calculations and all derivatives show intense blue emission upon UV excitation.
Beschreibung:Dedicated to Prof. Dr. Franz Effenberger on the occasion of his 80th birthday
Gesehen am 22.06.2023
Beschreibung:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.201000212

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