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. 2017 Jul 7;82(13):6958-6967.
doi: 10.1021/acs.joc.7b00639. Epub 2017 Jun 15.

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

Justin M Salvant  1 , Anne V Edwards  1 , Daniel Z Kurek  1 , Ryan E Looper  1
Affiliations

Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

Justin M Salvant et al. J Org Chem. .

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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Conflict of interest statement

Notes

The authors declare the following competing financial interest(s): R.E.L. has an equity position in Curza Global LLC.

Figures

Figure 1
Figure 1
Crystal structure of 4m (ellipsoids are shown at 35% probability level).
Scheme 1
Scheme 1
Second Generation Synthesis of ZNA
See this image and copyright information in PMC

References

    1. Sullivan JD, Giles RL, Looper RE. Curr Bioact Compd. 2009;5:39–78.
    2. Koswatta PB, Lovely CJ. Nat Prod Rep. 2011;28:511–528. - PubMed
    3. Roue M, Qué vrain E, Domart-Coulon, Bourguet-Kondracki M-L. Nat Prod Rep. 2012;29:739–751. - PubMed
    1. Bonafoux D, Chuaqui C, Boriack-Sjodin PA, Fitch C, Hankins G, Josiah S, Black C, Hetu G, Ling L, Lee W. Bioorg Med Chem Lett. 2009;19(3):912–918. - PubMed
    1. Tanaka K, Kanno T, Yanagisawa K, Inoue S, Hirayama N, Ikeda J. PLoS One. 2014;9(1):e87728. - PMC - PubMed
    1. LaMarche M, Borawski J, Bose A, Capacci-Daniel C, Colvin R, Dennehy M, Ding J, Dobler M, Drumm D, Gaither LA, Gao J, Jiang X, Lin K, McKeever U, Puyang X, Rama P, Thohan S, Tommasi R, Wagner K, Xiong X, Zabawa T, Zhu S, Wiedmann B. Antimicrob Agents Chemother. 56(10):2012. 5149–5156. - PMC - PubMed
    1. Zhang N, Zhang Z, Wong I, Wan S, Chow L, Jiang T. Eur J Med Chem. 2014;83:74–83. - PubMed

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