The Study of Reaction of Hexafluoro-1,4-Napthoquinone With Substituted 5-Aminopyrazoles

Abstract

For the first time, the interaction of perfluoro-1,4-naphthoquinone with various 5-aminopyrazoles was investigated. It was shown that three types of products can be obtained depending on the structure of starting aminopyrazole. For all examples, the substitution of one fluorine atom in quinone moiety was observed. Wherein, in most cases, the starting aminopyrazoles act as a C-nucleophile leading to 2-(5-aminopyrazol-4-yl)-3,5,6,7,8-pentafluoronaphthalene-1,4-diones. At the same time substrates unsubstituted at ring nitrogen atom regiospecifically react at aminogroup resulting in the formation of 2,5,6,7,8-pentafluoro-3-((pyrazol-5-yl)amino)naphthalene-1,4-diones. Besides that, the absence of steric hindrance in the pyrazole unit allowed us to direct the process at nitrogen atom in Position 2 and synthesize zwitter-ionic 3-(5-aminopyrazol-2-ium-2-yl)-5,6,7,8-tetrafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-olates. The structures of two types of obtained products were confirmed by x-ray analysis.