Issue 11, 2024

Modular synthetic strategies for dipyrrolopyrazines

Abstract

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.

Graphical abstract: Modular synthetic strategies for dipyrrolopyrazines

Supplementary files

Article information

Article type
Research Article
Submitted
19 Jan 2024
Accepted
08 Feb 2024
First published
04 Mar 2024

Org. Chem. Front., 2024,11, 2996-3003

Modular synthetic strategies for dipyrrolopyrazines

J. Kahle, A. V. Mackenroth, C. Hüßler, P. D. Römgens, P. Schimanski, P. Krämer, M. Brückner, T. Oeser, F. Rominger, M. Rudolph and A. S. K. Hashmi, Org. Chem. Front., 2024, 11, 2996 DOI: 10.1039/D4QO00119B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements