Institution: | 1. Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10–14, 55128 Mainz, Germany;2. Department of Chemistry, Johannes Gutenberg University Mainz, Johann-Joachim Becherweg 30, 55128 Mainz, Germany
Center for Biomolecular Magnetic Resonance (BMRZ), Goethe-University Frankfurt, Max-von-Laue Str. 9, 60438 Frankfurt/M, Germany;3. Department of Chemistry, Johannes Gutenberg University Mainz, Johann-Joachim Becherweg 30, 55128 Mainz, Germany;4. Department Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka 560–8531 Japan;5. Department of Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10–14, 55128 Mainz, Germany
Deceased 09/2019. |
Abstract: | The efficient production of many medicinally or synthetically important starting materials suffers from wasteful or toxic precursors for the synthesis. In particular, the aromatic non-protected primary amine function represents a versatile synthetic precursor, but its synthesis typically requires toxic oxidizing agents and transition metal catalysts. The twofold electrochemical amination of activated benzene derivatives via Zincke intermediates provides an alternative sustainable strategy for the formation of new C?N bonds of high synthetic value. As a proof of concept, we use our approach to generate a benzoxazinone scaffold that gained attention as a starting structure against castrate-resistant prostate cancer. Further improvement of the structure led to significantly increased cancer cell line toxicity. Thus, exploiting environmentally benign electrooxidation, we present a new versatile and powerful method based on direct C?H activation that is applicable for example the production of medicinally relevant compounds. |