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Paper | Regular issue | Vol 48, No. 7, 1998, pp. 1395 - 1406
Published online:
DOI: 10.3987/COM-98-8162
Acylation of Guanylhydrazones Derived from Cyclic Ketones: Synthesis of 3-Acylamino-1-cycloalkenyl-5-methyl-1H-1,2,4-triazoles

Zoltan Györgydeák and Wolfgang Holzer*

*Institute of Pharmaceutical Chemistry, University of Vienna, Währinger Strasse 14, A-1090 Vienna, Austria

Abstract

Reaction of guanylhydrazones derived from different cycloalkanones, 1-indanone and 4-chromanone, respectively, with excessive acetic anhydride leads to the formation of 3-acetylamino-1-cycloalkenyl-5-methyl-1H-1,2,4-triazoles. However, with camphor guanylhydrazone only the corresponding N,N’-diacetylguanylhydrazone was obtained, whereas 2-adamantone guanylhydrazone afforded 2-(3-acetylamino-5-methyl-1,2,4-triazol-1-yl)-2-adamantyl acetate. Detailed NMR spectroscopic studies (1H, 13C) with the title compounds and their guanylhydrazone precursors are presented.

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