Issue 19, 2025

A simple route to 2,3-benzodiazepines from substituted indenes

Abstract

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 1H NMR kinetic experiments.

Graphical abstract: A simple route to 2,3-benzodiazepines from substituted indenes

Supplementary files

Transparent peer review

To support increased transparency, we offer authors the option to publish the peer review history alongside their article.

View this article’s peer review history

Article information

Article type
Paper
Submitted
28 Feb 2025
Accepted
09 Apr 2025
First published
10 Apr 2025

Org. Biomol. Chem., 2025,23, 4710-4717

A simple route to 2,3-benzodiazepines from substituted indenes

E. S. Tarasova, O. V. Shurupova, S. A. Rzhevskiy, L. I. Minaeva, M. A. Topchiy and A. F. Asachenko, Org. Biomol. Chem., 2025, 23, 4710 DOI: 10.1039/D5OB00361J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements