A Direct Route into Fused Imidazo-diazines and Imidazo-pyridines Using Nucleophilic Nitrenoids in a Gold-Catalyzed Formal [3 + 2]-Dipolar Cycloaddition | Zendy

Miguel Garzón | Zendy; Paul Davies | Zendy

Open Access

A Direct Route into Fused Imidazo-diazines and Imidazo-pyridines Using Nucleophilic Nitrenoids in a Gold-Catalyzed Formal [3 + 2]-Dipolar Cycloaddition

Author(s) -

Miguel Garzón,

Paul Davies

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502346d

Subject(s) - chemistry , cycloaddition , pyridinium , nucleophile , alkyne , regioselectivity , catalysis , combinatorial chemistry , nucleophilic addition , stereochemistry , medicinal chemistry , organic chemistry

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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