Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow

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 to 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 multi-gram quantities of product in a safe and readily scalable manner thus demonstrating the value of this photochemical approach for future exploitations in industry.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Photochemical Synthesis of Pyrazolines from Tetrazoles in Flow ; day:08 ; month:12 ; year:2022
SynOpen ; (08.12.2022)

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

DOI
10.1055/a-1995-1859
URN
urn:nbn:de:101:1-2023012610380049614808
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:35 AM CEST

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Associated

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

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