Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2‑Cyanothiazole Derivatives

The expeditious synthesis of an API building block, 2-cyanothiazole, from cyanogen gas and a readily available dithiane is reported. A previously undisclosed partially saturated intermediate is formed, which can be further functionalized and isolated by the acylation of the hydroxy group. Dehydratio...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-07, Vol.88 (13), p.9594-9598
Main Authors: Prieschl, Michael, Sedelmeier, Joerg, Püntener, Kurt, Hildbrand, Stefan, Williams, Jason D., Kappe, C. Oliver
Format: Article
Language:English
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Summary:The expeditious synthesis of an API building block, 2-cyanothiazole, from cyanogen gas and a readily available dithiane is reported. A previously undisclosed partially saturated intermediate is formed, which can be further functionalized and isolated by the acylation of the hydroxy group. Dehydration using trimethylsilyl chloride furnished 2-cyanothiazole, which could be further converted to the corresponding amidine. The sequence provided a 55% yield over 4 steps. We envision that this work will spark further interest in cyanogen gas as a reactive and cost-effective synthetic reagent.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01110