Derivatives of Δ2-pyrazoline-products of 1,5-diaminotetrazole interaction with chalcone: Molecular structure and spectral properties

✍ Scribed by N.N. Kolos; B.V. Paponov; V.D. Orlov; M.I. Lvovskaya; A.O. Doroshenko; O.V. Shishkin

• Book ID: 103837273
• Publisher: Elsevier Science
• Year: 2006
• Tongue: English
• Weight: 429 KB
• Volume: 785
• Category: Article
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2005.10.004

✦ Synopsis

1,5-diaminotetrazole at conditions of its interaction with chalcones (1,3-diphenylpropenones) in hot DMF undergoes Dimroth rearrangement to 5-tetrazolylhydrazine, which results in formation of 1-(5-tetrazolyl)-3,5-diaryl-D 2 -pyrazolines (I). Structure of the obtained products was confirmed by their parallel synthesis and X-ray structural analysis. Unusual fluorescence behavior of the tetrazolopyrazolynes in polar solvents was attributed to the dissociation of their highly acidic tetrazole N-H group. The last hypothesis was confirmed at the investigation of the protolytic interactions of I with tertiary amine.