Gas-liquid flow hydrogenation of nitroarenes: Efficient access to a pharmaceutically relevant pyrrolobenzo[1,4]diazepine scaffold

Dimitriou, E; Jones, R; Pritchard, R; Miller, G; O'Brien, M

Abstract

Using a Tube-in-Tube device based on the amorphous Teflon AF-2400 fluoropolymer, a series of nitroarenes was hydrogenated to afford the corresponding aniline compounds. The system was then applied to the construction of a pyrrolobenzo[1,4]diazapene scaffold through a tandem hydrogenation-condensation-hydrogenation sequence.

• Journal Article Type: Article
• Acceptance Date: Sep 11, 2018
• Online Publication Date: Sep 18, 2018
• Publication Date: Nov 22, 2018
• Publicly Available Date: May 26, 2023
• Journal: Tetrahedron
• Print ISSN: 0040-4020
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 74
• Issue: 47
• Pages: 6795-6803
• DOI: https://doi.org/10.1016/j.tet.2018.09.025
• Keywords: Gas-liquid flow, Hydrogenation, Pyrrolobenzodiazepine, Reduction, Cyclisation
• Publisher URL: https://doi.org/10.1016/j.tet.2018.09.025