Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow

SynOpen

article

Adam Burke¹  Silvia Spiccio¹  Mara Di Filippo¹  Marcus Baumann¹ 

[1] School of Chemistry, University College Dublin, Science Centre South

关键词: flow chemistry;    photochemistry;    pyrazoline;    tetrazole;    click reaction;    drug-like heterocycles;   

DOI  :  10.1055/a-1995-1859

学科分类：精神健康和精神病学

来源: Thieme

【 摘 要 】

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.

【 授权许可】

CC BY|CC BY-NC-ND