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

Elsa M. Arce; Scott G. Lamont; Paul W. Davies

doi:10.1002/adsc.202000134

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

Elsa M. Arce
, Scott G. Lamont
, Paul W. Davies

Chemistry

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

231 Downloads (Pure)

Abstract

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.).

Original language	English
Pages (from-to)	2503-2509
Number of pages	7
Journal	Advanced Synthesis & Catalysis
Volume	362
Issue number	12
Early online date	24 Mar 2020
DOIs	https://doi.org/10.1002/adsc.202000134
Publication status	Published - 15 Jun 2020

Bibliographical 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.

Keywords

Annulations
Gold catalysis
Heterocycles
Sulfur
Ynamides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.202000134Licence: Creative Commons: Attribution (CC BY)

ArceE2020Sulfenyl
E. M. Arce, S. G. Lamont, P. W. Davies, Adv. Synth. Catal. 2020, 362, 2503
Final published version, 5.89 MBLicence: Creative Commons: Attribution (CC BY)

5 Citations
7 Article
1 Review article

Gold-catalyzed annulations with nucleophilic nitrenoids enabled by heteroatom-substituted alkynes
Davies, P., 27 Oct 2021, (E-pub ahead of print) In: The Chemical Record. 21, 12, p. 3964-3977
Research output: Contribution to journal › Article › peer-review

Open Access
File
184 Downloads (Pure)
Synthesis of N-Acyl pyridinium-N-aminides and their conversion to 4-aminooxazoles via a gold-catalyzed formal (3+2)-dipolar cycloaddition
Davies, P., Jannapureddy, R. & Ball, M., 2018, In: Organic Syntheses. 95, p. 112-126 15 p.
Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)
Alkynyl Thioethers in Gold-Catalyzed Annulations to form Oxazoles
Davies, P., Jannapu Reddy, R. & Ball-Jones, M., 16 Oct 2017, In: Angewandte Chemie (International Edition) . 56, 43, p. 13310–13313
Research output: Contribution to journal › Article › peer-review

Open Access
File
58 Citations (Scopus)

197 Downloads (Pure)
General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition
Davies, P., Garzon Sanz, M., Martinez Arce, E. & Jannapureddy, R., 18 Apr 2017, (E-pub ahead of print) In: Advanced Synthesis & Catalysis.
Research output: Contribution to journal › Article › peer-review

Open Access
File
14 Citations (Scopus)

297 Downloads (Pure)
Efficient and flexible synthesis of highly functionalised 4-aminooxazoles by a gold-catalysed intermolecular formal [3+2]-dipolar cycloaddition
Davies, P., Gillie, A. & Jannapureddy, R., 21 Jan 2016, In: Advanced Synthesis & Catalysis. 358, 2, p. 226-239
Research output: Contribution to journal › Article › peer-review

Open Access
53 Citations (Scopus)
Nucleophilic nitrenoids through π-acid catalysis: providing a common basis for rapid access into diverse nitrogen heterocycles
Davies, P. & Garzon Sanz, M., Aug 2015, In: Asian Journal of Organic Chemistry. 4, 8, p. 694-708 15 p.
Research output: Contribution to journal › Review article › peer-review

Open Access
File
76 Citations (Scopus)

340 Downloads (Pure)
A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition
Garzon, M. & Davies, P. W., 19 Sept 2014, In: Organic Letters. 16, 18, p. 4850-3 4 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
62 Citations (Scopus)

263 Downloads (Pure)

Studentship - Elsa Martinez Arce - Umpolung N-nucleophilic nitrene character of N,N-ylides
Davies, P. (Principal Investigator)
AstraZeneca
29/09/14 → 28/03/18
Project: Industry

Birmingham Environment for Academic Research (BEAR)
Facility/equipment: Equipment

Cite this

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

abstract = "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.).",

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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 Garz{\'o}n (UoB) are thanked for the donation of some ynamides. Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH Verlag GmbH \& Co. KGaA. Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",

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AU - Davies, Paul W.

N1 - 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.

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KW - Annulations

KW - Gold catalysis

KW - Heterocycles

KW - Sulfur

KW - Ynamides

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Fingerprint

Research output

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Equipment

Cite this