Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines
Justin M. Salvant, Ryan E. Looper, Daniel Z. Kurek, Anne V. Edwards
A regioselective base-mediated cyclization of mono-N-acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N3-Cbz-protected ene-guanidines, which found utility in the synthesis of naamidine A. Herein, we report the base-catalyzed hydroamination of mono-N-acylpropargylguanidines, which proceeds with the opposite regiochemistry to deliver isomerized N2-acyl-2-aminoimidazoles with broad substrate scope, circumventing the problematic regiospecific acylation of free 2-aminoimidazoles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00639

DOI: 10.1021/acs.joc.7b00639

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