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: | , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
08 June 2010
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| 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 
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| Verfasserangaben: | Sven Rotzoll, Benjamin Willy, Jan Schönhaber, Frank Rominger, and Thomas J.J. Müller |
MARC
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| 245 | 1 | 0 | |a Regiospecific three-component access to fluorescent 2,4-disubstituted quinolines via one-pot coupling-addition-cyclocondensation-sulfur extrusion sequence |c Sven Rotzoll, Benjamin Willy, Jan Schönhaber, Frank Rominger, and Thomas J.J. Müller |
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| 500 | |a Dedicated to Prof. Dr. Franz Effenberger on the occasion of his 80th birthday | ||
| 500 | |a Gesehen am 22.06.2023 | ||
| 520 | |a 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. | ||
| 650 | 4 | |a C-C coupling | |
| 650 | 4 | |a Computations | |
| 650 | 4 | |a Fluorescence | |
| 650 | 4 | |a Microwave chemistry | |
| 650 | 4 | |a Multicomponent reactions | |
| 650 | 4 | |a Quinolines | |
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