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

Baumann, M.; Baxendale, I.R.

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


Authors

M. Baumann



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.

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

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