Collect. Czech. Chem. Commun. 1994, 59, 731-735

Reaction of 4-Amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 2,5-Dimethoxytetrahydrofuran

Aykut A. Ikizler and Haydar Yüksek

Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey


A number of studies involving some reactions of 4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones have been made in recent years. On the other hand, the reactions of some N-aminoheteroaryls with 1,4-diketones or 1,4-dialdehydes to give N,N'-linked biheteroaryls have also been reported. In the present study, a series of 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones I were condensed in good yields with the succinaldehyde equivalent, 2,5-dimethoxytetrahydrofuran to give N,N'-bis(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-1,4-butanediimines II or 1-(3-alkyl-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)pyrroles III in nitrobenzene or acetic acid medium, respectively. To obtain more information on type II compounds, 3-methyl-4-ethylidenamino-4,5-dihydro-1H-1,2, 4-triazol-5-one (IV) was synthesized.