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A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives

Baumann, Marcus; Baxendale, Ian R.

A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives Thumbnail


Authors

Marcus Baumann



Abstract

A simple yet robust flow set-up for the efficient desulfurization of a series of thioimidazoles is presented, which generates the corresponding imidazole derivatives in high yields. The strategic choice of peristaltic over piston pumps allowed reliable delivery of the heterogeneous stream of the thioimidazole substrate into a T-piece where it reacted with NaNO2 in the presence of acetic acid. This approach enabled the controlled and safe formation of the reactive nitrosonium species without uncontrolled exposure to hazardous nitrous oxide by-products as observed in related batch protocols. The value of the resulting imidazole products was further demonstrated by their conversion into various esters representing new derivatives of the known analgesic etomidate through an efficient one-pot Corey–Gilman–Ganem oxidation procedure.

Citation

Baumann, M., & Baxendale, I. R. (2017). A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives. European Journal of Organic Chemistry, 2017(44), 6518-6524. https://doi.org/10.1002/ejoc.201700833

Journal Article Type Article
Acceptance Date Jul 9, 2017
Online Publication Date Aug 16, 2017
Publication Date Dec 1, 2017
Deposit Date Nov 20, 2017
Publicly Available Date Aug 16, 2018
Journal European Journal of Organic Chemistry
Print ISSN 1434-193X
Electronic ISSN 1099-0690
Publisher Wiley
Peer Reviewed Peer Reviewed
Volume 2017
Issue 44
Pages 6518-6524
DOI https://doi.org/10.1002/ejoc.201700833

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Accepted Journal Article (Supporting Information) (4.1 Mb)
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Copyright Statement
Supporting Information


Accepted Journal Article (587 Kb)
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Copyright Statement
This is the peer reviewed version of the following article: Baumann, Marcus & Baxendale, Ian R. (2017). A Continuous-Flow Method for the Desulfurization of Substituted Thioimidazoles Applied to the Synthesis of Etomidate Derivatives. European Journal of Organic Chemistry, 2017(44): 6518-6524, which has been published in final form at https://doi.org/10.1002/ejoc.201700833. This article may be used for non-commercial purposes in accordance With Wiley-VCH Terms and Conditions for self-archiving.





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