UV‐Induced 1, 3, 4‐Oxadiazole Formation from 5‐Substituted Tetrazoles and Carboxylic Acids in Flow. Issue 65 (12th October 2020)

• Record Type: Journal Article
• Authors: Green, Luke; Livingstone, Keith; Bertrand, Sophie; Peace, Simon; Jamieson, Craig
• Is Part Of: Chemistry. Volume 26:Issue 65(2020)
• Page Start: 14866
• Page End: 14870
• Publication Date: 2020-10-12
• Subjects: flow -- heterocycles -- Huisgen reaction -- nitrile imines -- photochemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202002896
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A range of 1, 3, 4‐oxadiazoles have been synthesized using a UV‐B activated flow approach starting from carboxylic acids and 5‐substituted tetrazoles. The application of UV light represents an attractive alternative to the traditional thermolytic approach and has demonstrated comparable efficiency and versatility, with a diverse substrate scope, including the incorporation of highly substituted amino acids. Abstract : A photochemical, flow‐based Huisgen synthesis of 1, 3, 4‐oxadiazoles from 5‐substituted tetrazoles and carboxylic acids has been developed. This has enabled the expedient and facile synthesis of a broad palette of heterocyclic derivatives which are of direct relevance to a range of applications including pharmaceuticals and materials science (see scheme).