Acylation of guanylhydrazones derived from cyclic ketones: Synthesis of 3-acylamino-1-cycloalkenyl-5-methyl-1H-1,2,4-triazoles

Article abstract of DOI:10.3987/com-98-8162

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'-diacetyl-guanylhydrazone 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.