Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow

Baumann, Marcus; Burke, Adam; Spiccio, Silvia; Di Filippo, Mara

Abstract

Pyrazolines and their pyrazole congeners are important heterocyclic building blocks with numerous applications in the fine chemical industries. However, traditional routes towards these entities are based on multistep syntheses generating substantial amounts of chemical waste. Here we report an alternative approach using UV-light to convert tetrazoles into pyrazolines via a reagent-free photo-click strategy. This route generates nitrile imine dipoles in situ that are trapped with different dipolarophiles rendering a selection of these heterocyclic targets in high chemical yields. A continuous flow method is ultimately realized that generates multigram quantities of product in a safe and readily scalable manner thus demonstrating the value of this photochemical approach for future exploitations in industry.

Citation

Baumann, M., Burke, A., Spiccio, S., & Di Filippo, M. (2023). Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow. SynOpen, 07(01), https://doi.org/10.1055/a-1995-1859

• Journal Article Type: Article
• Acceptance Date: Dec 7, 2022
• Online Publication Date: Dec 8, 2022
• Publication Date: 2023
• Deposit Date: Mar 6, 2023
• Publicly Available Date: Mar 6, 2023
• Journal: SynOpen
• Electronic ISSN: 2509-9396
• Publisher: Thieme Open
• Peer Reviewed: Peer Reviewed
• Volume: 07
• Issue: 01
• DOI: https://doi.org/10.1055/a-1995-1859
• Public URL: https://durham-repository.worktribe.com/output/1180425