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Volumn 16, Issue 18, 2014, Pages 4850-4853

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

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EID: 84925865470     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502346d     Document Type: Article
Times cited : (77)

References (52)
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    • Katritzky, A. R., Ramsden, A. C., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon-Elsevier Science: Oxford
    • (b) Couty, F.; Evano, G. In Comprehensive Heterocyclic Chemistry III; Katritzky, A. R., Ramsden, A. C., Scriven, E. F. V., Taylor, R. J. K., Eds.; Pergamon-Elsevier Science: Oxford, 2008; Vol. 11, pp 409-499 and references therein. Recent examples
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    • Examples of nucleophilic nitrenoids in gold-catalyzed intramolecular reactions: (a) Gorin, D. J.; Davis, N. R; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260.
    • (2005) Am. Chem. Soc. , vol.127 , pp. 11260
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    • Intermolecular tosylnitrene addition to ynamides: Li, C.; Zhang, L. Org. Lett. 2011, 13, 1738.
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    • Li, C.1    Zhang, L.2
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    • A stepwise mechanism where pyridine is eliminated as a distinct step prior to cyclization can be envisaged but is considered less likely. See ref 6 and related mechanisms in: (a) Kramer, S.; Skrydstrup, T. Angew. Chem., Int. Ed. 2012, 51, 4681.
    • (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 4681
    • Kramer, S.1    Skrydstrup, T.2
  • 41
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    • Recent work from our group using gold activation of ynamides to regiocontrol additions: (a) Davies, P. W.; Cremonesi, A; Martin, N. Chem. Commun. 2011, 47, 379.
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    • For recent representative examples of regiocontrolled goldcatalyzed intermolecular addition to ynamides using different types of nucleophiles, see: (a) Xin, Z.; Kramer, S.; Overgaard, J.; Skrydstrup, T. Chem.-Eur. J. 2014, 20, 7926.
    • (2014) Chem.-Eur. J. , vol.20 , pp. 7926
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    • CCDC 1018314 and 1018315 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


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