A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition

Miguel Garzon; Paul W Davies

doi:10.1021/ol502346d

A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition

Miguel Garzon, Paul W Davies

Chemistry

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

62 Citations (Scopus)

203 Downloads (Pure)

Abstract

Pyridinium N-(heteroaryl)aminides can be employed as robust and practical synthetic equivalents of nucleophilic 1,3-N,N-dipoles in a formal cycloaddition onto electron-rich alkynes under gold catalysis. Convergent and regioselective access to five types of imidazo-fused heteroaromatics is provided from the appropriate aminide. The efficient transformation accommodates significant structural variation around the aminide, ynamide, or indolyl-alkyne reactants and tolerates sensitive functional groups.

Original language	English
Pages (from-to)	4850-3
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	18
DOIs	https://doi.org/10.1021/ol502346d
Publication status	Published - 19 Sept 2014

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10.1021/ol502346d

Garzon_Davies_Direct_route_fused_imidazo_diazines_Organic_Letters_2014
Eligibility for repository : checked 18/02/2015
Final published version, 1.08 MBLicence: Creative Commons: Attribution (CC BY)

62 Citations
3 Article
1 Entry for encyclopedia/dictionary
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
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Sulfenyl ynamides in gold catalysis: synthesis of oxo‐functionalised 4‐aminoimidazolyl fused compounds by intermolecular annulation reactions
Arce, E. M., Lamont, S. G. & Davies, P. W., 15 Jun 2020, In: Advanced Synthesis & Catalysis. 362, 12, p. 2503-2509 7 p.
Research output: Contribution to journal › Article › peer-review

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5 Citations (Scopus)

156 Downloads (Pure)
1-(2-Pyrimidinylamino)pyridinium Inner Salt
Davies, P., 11 Apr 2017, e-EROS Encyclopedia of Reagents for Organic Synthesis. Wiley, 10.1002/047084289X.rn02042
Research output: Chapter in Book/Report/Conference proceeding › Entry for encyclopedia/dictionary
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.
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14 Citations (Scopus)

239 Downloads (Pure)
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

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76 Citations (Scopus)

281 Downloads (Pure)

Cite this

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title = "A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition",

abstract = "Pyridinium N-(heteroaryl)aminides can be employed as robust and practical synthetic equivalents of nucleophilic 1,3-N,N-dipoles in a formal cycloaddition onto electron-rich alkynes under gold catalysis. Convergent and regioselective access to five types of imidazo-fused heteroaromatics is provided from the appropriate aminide. The efficient transformation accommodates significant structural variation around the aminide, ynamide, or indolyl-alkyne reactants and tolerates sensitive functional groups.",

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A direct route into fused imidazo-diazines and imidazo-pyridines using nucleophilic nitrenoids in a gold-catalyzed formal [3 + 2]-dipolar cycloaddition

Abstract

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Research output

Gold-catalyzed annulations with nucleophilic nitrenoids enabled by heteroatom-substituted alkynes

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

1-(2-Pyrimidinylamino)pyridinium Inner Salt

General Entry into o-,o’-Heteroatom-Linked N-(Hetero)aryl Imidazole Motifs by Gold-Catalysed Formal [3+2]-Dipolar Cycloaddition

Nucleophilic nitrenoids through π-acid catalysis: providing a common basis for rapid access into diverse nitrogen heterocycles

Cite this