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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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Main Authors: Kahle, Justin (Author) , Mackenroth, Alexandra (Author) , Hüßler, Christopher (Author) , Römgens, Patrick (Author) , Schimanski, Paul (Author) , Krämer, Petra (Author) , Brückner, Margit (Author) , Oeser, Thomas (Author) , Rominger, Frank (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 04 Mar 2024
In: Organic chemistry frontiers
Year: 2024, Volume: 11, Issue: 11, Pages: 2996-3003
ISSN:2052-4129
DOI:10.1039/D4QO00119B
Online Access: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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Author Notes: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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Summary: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.
Item Description:Zuerst veröffentlicht: 4. März 2024
Gesehen am 12.07.2024
Physical Description:Online Resource
ISSN:2052-4129
DOI:10.1039/D4QO00119B

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