A Continuous Flow Synthesis and Derivatisation of 1,2,4-Thiadiazoles

Baumann, M.; Baxendale, I.R.

Abstract

A continuous flow process is presented that enables the efficient synthesis and derivatization of 1,2,4-thiadiazole heterocycles. Special attention was given to the safe handling of the versatile yet hazardous trichloromethane sulfenylchloride reagent including its in-line quenching in order to eliminate malodourous and corrosive by-products. Based on this flow method gram quantities of 5-chloro-3-phenyl-1,2,4-thiadiazole were safely prepared allowing for further elaboration of this valuable building block by reaction with different nitrogen-, sulfur- and oxygen-based nucleophiles. This synthetic approach was subsequently applied to generate a series of bromophenyl-5-chloro-1,2,4-thiadiazoles providing a valuable entry towards further structural diversification on this important heterocyclic scaffold.

Citation

Baumann, M., & Baxendale, I. (2017). A Continuous Flow Synthesis and Derivatisation of 1,2,4-Thiadiazoles. Bioorganic and Medicinal Chemistry, 25(23), 6218-6223. https://doi.org/10.1016/j.bmc.2017.01.022

• Journal Article Type: Article
• Acceptance Date: Jan 20, 2017
• Online Publication Date: Jan 23, 2017
• Publication Date: Dec 1, 2017
• Deposit Date: Jan 24, 2017
• Publicly Available Date: Jan 23, 2018
• Journal: Bioorganic and Medicinal Chemistry
• Print ISSN: 0968-0896
• Publisher: Elsevier
• Peer Reviewed: Peer Reviewed
• Volume: 25
• Issue: 23
• Pages: 6218-6223
• DOI: https://doi.org/10.1016/j.bmc.2017.01.022
• Public URL: https://durham-repository.worktribe.com/output/1366630