A simple route to 2,3-benzodiazepines from substituted indenes
Herein, we present a two-step approach for synthesizing 2,3-benzodiazepines from substituted indenes. This process involves oxidation of indenes to 1,5-diketones followed by their cyclocondensation with hydrazine hydrate. The optimized conditions for a wide range of substituted 2,3-benzodiazepines, including the well-known anxiolytic tofisopam, were investigated. A detailed mechanism for the cyclization of 1,5-diketones with hydrazine hydrate was established using <sup>1</sup>H NMR kinetic experiments.
Authors
- Andrey F. Asachenko (ORCID: https://orcid.org/0000-0001-8638-9261)
- Lidiya I. Minaeva (ORCID: https://orcid.org/0000-0001-6373-6400)
- Sergey A. Rzhevskiy (ORCID: https://orcid.org/0000-0003-4732-9949)
- Olga V. Shurupova (ORCID: https://orcid.org/0000-0002-2582-9929)
- Ekaterina Tarasova (ORCID: https://orcid.org/0009-0003-3870-1291)
- Maxim A. Topchiy (ORCID: https://orcid.org/0000-0002-6604-7034)
Institutions
- Russian Academy of Sciences (RU)
- A.V. Topchiev Institute of Petrochemical Synthesis (RU)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00361j
- Primary Topic
- Synthesis and pharmacology of benzodiazepine derivatives
- Type
- article
- Field-Weighted Citation Impact
- 0.00