Highly Regioselective Dehydrogenative Hydrazination of Tropones.

J Org Chem

Hefei National Research Center for Physical Sciences at the Microscale, Key Laboratory of Precision and Intelligent Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China.

Published: December 2024

Direct C(sp)-H bond functionalization of the tropone skeleton constitutes an atom-economical strategy to access substituted tropones that exist in some bioactive compounds. Herein, we report a convenient method for the preparation of 2-hydrazinotropones via C(sp)-H bond functionalization. A variety of tropones participated in the dehydrogenative hydrazination reaction with hydrazine, delivering structurally diverse 2-hydrazinotropones in moderate to good yields with extremely high regioselectivity. This method is featured by operational simplicity and metal-free reaction conditions, thereby tolerating various functional groups.

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Source
http://dx.doi.org/10.1021/acs.joc.4c02358DOI Listing

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