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Double Ring-Closing Approach for the Synthesis of 2,3,6,7-Substituted Anthracene Derivatives

preprint
submitted on 31.03.2020 and posted on 01.04.2020 by Birgit Meindl, Katharina Pfennigbauer, Berthold Stöger, Martin Heeney, Florian Glöcklhofer
Anthracene derivatives have been used for a wide range of applications and many different synthetic methods for their preparation have been developed. However, despite continued synthetic efforts, introducing substituents in some positions has remained difficult. Here we present 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. Further modification of the precursor is expected to enable the introduction of additional substituents in other positions and may even enable the synthesis of fully substituted anthracene derivatives by the presented approach.

Funding

Marie Skłodowska-Curie grant No 796024

Royal Society

Wolfson Foundation

History

Email Address of Submitting Author

f.glocklhofer@imperial.ac.uk

Institution

Imperial College London

Country

United Kingdom

ORCID For Submitting Author

0000-0002-6911-8563

Declaration of Conflict of Interest

No conflict of interest

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