1,4,5,6-Tetrahydro-1,2,4-triazin-6-ones and 3-amino-1-imidazolin-4-ones from 2-aminoacylhydrazines

✍ Scribed by P. S. Lobanov; A. L. Grebelkin; D. I. Zaitsev; V. A. Gindin; A. A. Potekhin

• Publisher: Springer US
• Year: 1991
• Tongue: English
• Weight: 340 KB
• Volume: 27
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00486809

✦ Synopsis

The 2-aminoacylhydrazines form 1,4,5,6-tetrahydro-l,2,4-triazin-6-ones with orthoesters and iminoesters. Benzylidene and isopropylidene derivatives of the 2-aminoacylhydrazines give the corresponding derivatives of 3-amino-l-imidazolin-4-ones with the same reagents.

In connection witL ~.he study of the reactivity of 2-aminoacylhydrazines having some nucleophilic centers and the capacity to form differer, types of heterocyclic compounds, we turned to the investigatign of the reactions of 2aminoacylhydrazines and their derivatives with orthoesters and iminoesters. The formation of both the six-membered triazines (III) and the five-membered imidazolines (IV) could be expected in these reactions. It was found that the sole products of the reactions of the 2-aminoacylhydrazines (I) with the orthoesters (II) are the tetrahydrotriazines (III) (cf. Table 1), isolated with yields of 60-70%. O 0 O 9 " NHNIt2 | + R2C(0C.,}I5)3 l -...m -~,-NIl,