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Iron Trichloride and Air Mediated Guanylation of Acylthioureas. An Ecological Route to Acylguanidines: Scope and Mechanistic Insights

  • Recently we introduced iron trichloride as an environmentally benign and cost-efficient reagent for the synthesis of N-benzoylguanidines. This highly attractive synthetic approach grants access to a broad spectrum of N-benzoylguanidines under mild conditions in short reaction times. In this work we present an extended scope of Our methodology along with the results obtained from mechanistic studies via in situ IR spectroscopy in combination with LC (liquid chromatography)-MS analyses. On the basis of these new mechanistic insights we were able to optimize the synthetic protocol and to develop an alternative mechanistic proposal. In this context the symbiotic roles of iron trithloride and oxygen in the guanylation process are highlighted.

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Author details:Simon Pape, Pablo WessigORCiDGND, Heiko Brunner
DOI:https://doi.org/10.1021/acs.joc.6b00600
ISSN:0022-3263
Pubmed ID:https://pubmed.ncbi.nlm.nih.gov/27181741
Title of parent work (English):The journal of organic chemistry
Publisher:American Chemical Society
Place of publishing:Washington
Publication type:Article
Language:English
Year of first publication:2016
Publication year:2016
Release date:2020/03/22
Volume:81
Number of pages:12
First page:4701
Last Page:4712
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
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