21,23-Dithia-3,13-diazaporphycenes - novel aromatic porphycene analogues incorporating thiazole

The syntheses of the first examples of aromatic thiazole-containing porphycene analogues 3 have been accomplished by oxidation of the corresponding 3,20:10,13-diepithio-6,9:16,19-diimino-1,11-diaza[20]annulenes 9 with DDQ. Compounds 9a−c have been synthesized by McMurry coupling reaction of the difo...

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Hauptverfasser: Nußbaumer, Thomas (VerfasserIn) , Krieger, Claus (VerfasserIn) , Neidlein, Richard (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2000
In: European journal of organic chemistry
Year: 2000, Heft: 13, Pages: 2449-2457
ISSN:1099-0690
DOI:10.1002/1099-0690(200007)2000:13<2449::AID-EJOC2449>3.0.CO;2-F
Online-Zugang:Verlag, kostenfrei registrierungspflichtig, Volltext: http://dx.doi.org/10.1002/1099-0690(200007)2000:13<2449::AID-EJOC2449>3.0.CO;2-F
Verlag, kostenfrei registrierungspflichtig, Volltext: http://onlinelibrary.wiley.com/doi/10.1002/1099-0690(200007)2000:13<2449::AID-EJOC2449>3.0.CO;2-F/abstract
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Verfasserangaben:Thomas Nußbaumer, Claus Krieger, and Richard Neidlein
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Zusammenfassung:The syntheses of the first examples of aromatic thiazole-containing porphycene analogues 3 have been accomplished by oxidation of the corresponding 3,20:10,13-diepithio-6,9:16,19-diimino-1,11-diaza[20]annulenes 9 with DDQ. Compounds 9a−c have been synthesized by McMurry coupling reaction of the diformylated 2-(1H-pyrrol-2-yl)thiazoles 8a−c, readily available by a three-step reaction sequence using 2-pyrrolethiocarboxamide (4) as starting material. The aromaticity of the 21,23-dithia-3,13-diazaporphycenes 3 is clearly established by NMR and UV/Vis spectroscopy and verified by X-ray crystal structure analysis of 3b.
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Beschreibung:Online Resource
ISSN:1099-0690
DOI:10.1002/1099-0690(200007)2000:13<2449::AID-EJOC2449>3.0.CO;2-F