Formation of derivatives of 1,2,4-triazoloquinazolines in the reactions of 3-amino-1,2,4-triazoles with cyclohexanone

✍ Scribed by S. M. Desenko; V. D. Orlov; Kh. éstrada

• Publisher: Springer US
• Year: 1990
• Tongue: English
• Weight: 141 KB
• Volume: 26
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00509729

✦ Synopsis

It is known [1, 2] that the reactions of binucleophiles with ketones containing the activated methyl or methylene group, or with the products of the self-condensation of these ketones, may lead to one and the same substance. We established that the boiling of the solutions of the 3-amino-l,2,4-triazoles (Ia, b) and cyclohexanone in DMF in the course of 4-6 h (reaction A) leads to the formation of the compounds (IIa, b), for which the mass spectra and the data of the elemental analysis indicate that the condensation of the ketone with the amine takes place with the 2:1 molar ratio, and with the cleavage of 2 moles of water.

Under the analogous conditions, the condensation of the amines (Ia, b) with 2-cyclohexylidenecyclohexane (reaction B) leads to the formation of the substances (IIIa, b) having the same composition and molecular mass as the compounds (II). However, according to the data of the TLC, the IR spectra (the region of the fingerprints), and the PMR spectra, the compounds (II) and (III) are different discrete substances; this permitted the proposition that the isomeric derivatives of 1,2,4-triazoloquinazolines are formed in the reactions A and B. r !