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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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Main Authors: Rudolph, Matthias (Author) , 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) , Hashmi, A. Stephen K. (Author)
Format: Database Research Data
Language:English
Published: Heidelberg Universität 2025-02-24
DOI:10.11588/DATA/TEYEG6
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Forschungsdaten
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Online Access: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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Author Notes: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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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:Gefördert durch: Deutsche Forschungsgemeinschaft (DFG): SFB 1249
Gesehen am 17.02.2025
Physical Description:Online Resource
DOI:10.11588/DATA/TEYEG6

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