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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

Miguel Garzón and Paul W. Davies*

*Haworth Building, School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, U.K., Email: p.w.daviesbham.ac.uk

M. Garzón, P. W. Davies, Org. Lett., 2014, 16, 4850-4853.

DOI: 10.1021/ol502346d (free Supporting Information)


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Abstract

Pyridinium N-(heteroaryl)aminides are robust and practical synthetic equivalents of nucleophilic 1,3-N,N-dipoles in a Au-catalyzed formal cycloaddition onto electron-rich alkynes. Convergent and regioselective access to five types of imidazo-fused heteroaromatics is provided from the appropriate aminide. The efficient transformation tolerates significant structural variation.

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Key Words

benzo-fused N-Heterocycles


ID: J54-Y2014