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1 Polish Journal of Chemistry

1 2007

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Synthesis and Structure of Mono- and Disubstituted Derivatives of 4,5-Dihydro-1H-1,2,4-triazol-5-one

Pitucha M., Dobosz M., Stępniak K., Dybała I., Kozioł A. E.

Polish Journal of Chemistry

2007

Vol. 81, nr 12

2103-2114

In the reaction of hydrazide of 1,2,4-triazol-1-acetic acid with isocyanates the semicarbazide derivatives were obtained (Ia-Ii). Depending on the chemical nature of the starting isocyanate, cyclization of Ia-Ii in alkaline medium led to formation of three groups of derivatives of 4,5-dihydro-1H-1,2,4-triazol-5-one (IIa-IIi). Alkyl and aryl substituents of semicarbazides formed 3,4-disubstituted compounds (IIa-IIf), the ethoxycarbonyl group promoted formation of 3-substituted compound IIg, while compounds IIh and IIi are 4-substituted triazol-5-ones resulting from benzoyl and benzenesulfonyl isocyanates. Molecular structures of three products (IIb, IIc, IId) were confirmed by the X-ray structure analysis. Different substituents at the N4 atom (ethyl in IIb, cyclohexyl in IIc and 1-naphthyl in IId) influence the molecular association pattern in the crystal structure.