Modular synthetic strategies for dipyrrolopyrazines [data]

DOI

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.

Identifier
DOI https://doi.org/10.11588/DATA/TEYEG6
Related Identifier IsCitedBy https://doi.org/10.1039/D4QO00119B
Metadata Access https://heidata.uni-heidelberg.de/oai?verb=GetRecord&metadataPrefix=oai_datacite&identifier=doi:10.11588/DATA/TEYEG6
Provenance
Creator Rudolph, Matthias; Kahle, Justin ORCID logo; Mackenroth, Alexandra V.; Hüßler, Christopher ORCID logo; Römgens, Patrick ORCID logo; Schimanski, Paul; Krämer, Petra; Brückner, Margit; Oeser, Thomas; Rominger, Frank; Hashmi, A. Stephen K. ORCID logo
Publisher heiDATA
Contributor Rudolph, Matthias
Publication Year 2025
Funding Reference Deutsche Forschungsgemeinschaft (DFG) SFB 1249
Rights CC BY 4.0; info:eu-repo/semantics/openAccess; http://creativecommons.org/licenses/by/4.0
OpenAccess true
Contact Rudolph, Matthias (Heidelberg University, Institute of Organic Chemistry)
Representation
Resource Type Dataset
Format application/zip; text/plain
Size 4172592; 1001924864; 2740606; 876; 1870713
Version 1.0
Discipline Chemistry; Engineering Sciences; Materials Science; Materials Science and Engineering; Natural Sciences