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Updated: Mar 1, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines
Justin M Salvant1, Anne V Edwards1, Daniel Z Kurek1
1Department of Chemistry, University of Utah , 315 South 1400 East, Salt Lake City, Utah 84112, United States.
Abstract:
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.
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