Work

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

Year: 2017

Type: article

Abstract: A regioselective base-mediated cyclization of mono- N -acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N 3 -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 N 2 -acyl-2-aminoimidazoles with broad substrate scope, circumventing the problematic regiospecific acylation of free 2-aminoimidazoles.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.7b00639

Authors: Justin M. Salvant, Anne V. Edwards, Daniel Z. Kurek, Ryan E. Looper

Institution: University of Utah

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: Synthetic and biological investigations of 2-aminoimidazole derived natural products., G878062147