Modular synthetic strategies for dipyrrolopyrazines [data]
Herein we describe the synthesis of dipyrrolopyrazines via a tandem-Sonogashira coupling with subsequent direct cyclisation of the resulting bisalkynes. The key precursor, di-tert-butyl (3,6-dichloropyrazine-2,5-diyl)dicarbamate, can be easily obtained on a large scale. Bidirectional cross-couplings...
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| Hauptverfasser: | , , , , , , , , , , |
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| Dokumenttyp: | Datenbank Forschungsdaten |
| Sprache: | Englisch |
| Veröffentlicht: |
Heidelberg
Universität
2025-02-24
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| DOI: | 10.11588/DATA/TEYEG6 |
| Schlagworte: | |
| Online-Zugang: | Resolving-System, kostenfrei, Volltext: https://doi.org/10.11588/DATA/TEYEG6 Verlag, kostenfrei, Volltext: https://heidata.uni-heidelberg.de/dataset.xhtml?persistentId=doi:10.11588/DATA/TEYEG6 
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| Verfasserangaben: | Matthias Rudolph, Justin Kahle, Alexandra V. Mackenroth, Christopher Hüßler, Patrick Römgens, Paul Schimanski, Petra Krämer, Margit Brückner, Thomas Oeser, Frank Rominger, A. Stephen K. Hashmi |
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| 245 | 1 | 0 | |a Modular synthetic strategies for dipyrrolopyrazines [data] |c Matthias Rudolph, Justin Kahle, Alexandra V. Mackenroth, Christopher Hüßler, Patrick Römgens, Paul Schimanski, Petra Krämer, Margit Brückner, Thomas Oeser, Frank Rominger, A. Stephen K. Hashmi |
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| 520 | |a Herein we describe the synthesis of dipyrrolopyrazines via a tandem-Sonogashira coupling with subsequent direct cyclisation of the resulting bisalkynes. The key precursor, di-tert-butyl (3,6-dichloropyrazine-2,5-diyl)dicarbamate, can be easily obtained on a large scale. Bidirectional cross-couplings yield either the diyne or dipyrrolopyrazine scaffolds selectively. When the intermediate bisalkynes are cyclised with IPrAuNTf2, an in situ deprotection of the Boc-group is observed, giving access to the N-unsubstituted dipyrrolopyrazines. Functionalisation of the pyrrolo-CH or NH-moiety allows further adjustment of solubility, processability and optoelectronic properties. Photophysical studies demonstrate remarkable stability and high quantum yields. | ||
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