Sulfenyl ynamides in gold catalysis: synthesis of oxo‐functionalised 4‐aminoimidazolyl fused compounds by intermolecular annulation reactions

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Functionalised N-heterocyclic pyridinium N-aminides have been designed and synthesised to evaluate a nitrenoid-based annulation strategy into imidazole-fused oxo-substituted frameworks of importance to medicinal and agrochemical discovery programmes. Sulfenyl substituted ynamides were identified as privileged reactants affording productive gold-catalysed annulation reactions with these and other nitrenoids. This annulation method provides selective and efficient access into geminally amino-sulfenyl substituted nitrogen heterocycles under mild reaction conditions. (Figure presented.).

Bibliographic note

Funding Information: We thank the University of Birmingham and AstraZeneca plc for funding (studentship to EMA). The authors gratefully acknowledge support from the Centre for Chemical and Materials Analysis in the School of Chemistry at UoB and its staff. Matthew Wakeling and Dr Miguel Garzón (UoB) are thanked for the donation of some ynamides. Publisher Copyright: © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.


Original languageEnglish
Pages (from-to)2503-2509
Number of pages7
JournalAdvanced Synthesis & Catalysis
Issue number12
Early online date24 Mar 2020
Publication statusPublished - 15 Jun 2020


  • Annulations, Gold catalysis, Heterocycles, Sulfur, Ynamides

ASJC Scopus subject areas