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. 2022 Nov 4;24(43):7924-7927.
doi: 10.1021/acs.orglett.2c02996. Epub 2022 Oct 20.

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

Storm Hassell-Hart  1 , Elisa Speranzini  1 , Sirihathai Srikwanjai  1 , Euan Hossack  2 , S Mark Roe  2 , Daren Fearon  3 , Daniel Akinbosede  2 , Stephen Hare  2 , John Spencer  1
Affiliations

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

Storm Hassell-Hart et al. Org Lett. .

Abstract

A library of thiazoles and selenothiazoles were synthesized via Ir-catalyzed ylide insertion chemistry. This process is a functional group, particularly heterocycle-substituent tolerant. This 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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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Hantzch Thiazole Synthesis
Scheme 2
Scheme 2. Thiazole Synthesis from Sulfonium Ylides
Scheme 3
Scheme 3. Further Cyclization Chemistry
Scheme 4
Scheme 4. Thioamide Insertions
Scheme 5
Scheme 5. Selenazole Synthesis
Scheme 6
Scheme 6. PTH Hit Based Library
See this image and copyright information in PMC

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