4.7 Article

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

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JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 13, 页码 6958-6967

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00639

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  1. National Institutes of Health Institute of General Medical Sciences [2R01GM90082-A1]

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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.

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