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Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction

Storm Hassell-Hart*, Elisa Speranzini, Sirihathai Srikwanjai, Euan Hossack, S. Mark Roe, Daren Fearon, Daniel Akinbosede, Stephen Hare and John Spencer*

*Department of Chemistry, School of Life Sciences, University of Sussex, Brighton BN1 9QJ, U.K., Email: s.hassell-hartucl.ac.uk, j.spencersussex.ac.uk

S. Hassell-Hart, E. Speranzini, S. Srikwanjai, E. Hossack, S. M. Roe, D. Fearon, D. Akinbosede, S. Hare, J. Spencer, Org. Lett., 2022, 24, 7924-7927.

DOI: 10.1021/acs.orglett.2c02996


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Abstract

A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. The reaction was applied to the synthesis of fanetizole, an anti-inflammatory drug, and a thiazole-containing drug fragment that binds to the peptidyl-tRNA hydrolase (Pth) in Neisseria gonorrheae bacteria.


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General Procedure for the Synthesis of 1,3-Thiazoles/Selenazoles

A mixture of respective β-ketosulfoxonium ylide (1.0 eq, 0.408 mmol), urea/thioamide/selenourea (1.5 eq, 0.612 mmol) and DCE (1 mL) was heated to 80 C and to the mixture was added [Ir(cod)Cl]2 (27.4 mg, 10 mol%, 0.041 mmol). The resulting mixture was stirred for 24 h at 80 C. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The resulting residue was purified by automated column chromatography to give the title compound.


Key Words

Thiazoles


ID: J54-Y2022