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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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
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cited_by cdi_FETCH-LOGICAL-a430t-16d118722152b0037a48ebec7179774f39f7c813d4c5784f1c3bfb710020943f3
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container_issue 13
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container_title Journal of organic chemistry
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creator Prieschl, Michael
Sedelmeier, Joerg
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description 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.
doi_str_mv 10.1021/acs.joc.3c01110
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title Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2‑Cyanothiazole Derivatives
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