Modular synthetic strategies for dipyrrolopyrazines
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: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
04 Mar 2024
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| In: |
Organic chemistry frontiers
Year: 2024, Jahrgang: 11, Heft: 11, Pages: 2996-3003 |
| ISSN: | 2052-4129 |
| DOI: | 10.1039/D4QO00119B |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D4QO00119B Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2024/qo/d4qo00119b 
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| Verfasserangaben: | Justin Kahle, Alexandra V. Mackenroth, Christopher Hüßler, Patrick D. Römgens, Paul Schimanski, Petra Krämer, Margit Brückner, Thomas Oeser, Frank Rominger, Matthias Rudolph and 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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