Journal of Organic Chemistry: Double ring closing

Our work reporting a double ring-closing approach for the synthesis of anthracene derivatives has been accepted for publication in the Journal of Organic Chemistry.

In the paper, we report a method for the synthesis of 2,3,6,7-substituted anthracene derivatives, one of the most challenging anthracene substitution patterns to obtain. The method is exemplified by the preparation of 2,3,6,7-anthracenetetracarbonitrile and employs a newly developed, stable, protected 1,2,4,5-benzenetetracarbaldehyde as the precursor. The precursor can be obtained in two scalable synthetic steps from 2,5-dibromoterephthalaldehyde and is converted into the anthracene derivative by a double intermolecular Wittig reaction under very mild conditions, followed by a deprotection and intramolecular double ring-closing condensation reaction.

Congratulations to first authors Birgit Meindl and Katharina Pfennigbauer!

You can read the paper here or the the open access preprint here.

B. Meindl, K. Pfennigbauer, B. Stöger, M. Heeney, F. Glöcklhofer,* Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives, J. Org. Chem. 2020, 85, 8240-8244