Efficient electrosynthesis of thiazolidin-2-imines via oxysulfurization of thiourea-tethered terminal alkenes using the flow microreactor

Islam, Muhammad, Kariuki, Benson M. ORCID: https://orcid.org/0000-0002-8658-3897, Shafiq, Zahid, Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 and Ahmed, Nisar ORCID: https://orcid.org/0000-0002-7954-5251 2018. Efficient electrosynthesis of thiazolidin-2-imines via oxysulfurization of thiourea-tethered terminal alkenes using the flow microreactor. European Journal of Organic Chemistry 10.1002/ejoc.201801688

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Abstract

Sulfur‐containing scaffolds play a significant role in many important biological processes. The thiazole‐2‐imine derivatives have gained significant biological attention due to their interesting pharmacological activities and act as potential therapeutic agents. Many of their syntheses suffer from the drawbacks such as the handling of toxic reagents, harsh reaction conditions, longer reaction times and tedious separation procedures. To their easy access, we applied first time flow electrochemical approach under free supporting electrolytes conditions and without the use of expensive catalysts and reagents. This is not only the first electrochemical cyclisation to access thiazolidin‐2‐imines also represents the first intramolecular sulfurisation of unfuctionalised terminal alkenes. This flow electrolysis of N‐allylic thioureas generates radical intermediates of nitrogen and sulfur that cyclised via oxysulfurisation of terminal alkenes and gives thiazolidin‐2‐imines with good to high yields under mild, green and environmentally friendly conditions.

Item Type:	Article
Date Type:	Published Online
Status:	Published
Schools:	Chemistry
Publisher:	Wiley
ISSN:	1434-193X
Date of First Compliant Deposit:	3 December 2018
Date of Acceptance:	20 November 2018
Last Modified:	22 Nov 2024 13:15
URI:	https://orca.cardiff.ac.uk/id/eprint/117325

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