Synthesis of substituted 5,6,7,8-tetrafluoro-1H-benzo[f]indol-4,9-diones based on the reaction of hexafluoro-1,4-napthoquinone with methyl 3-aminocrotonates

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Synthesis of substituted 5,6,7,8-tetrafluoro-1H-benzo[f]indol-4,9-diones based on the reaction of hexafluoro-1,4-napthoquinone with methyl 3-aminocrotonates

Journal of Heterocyclic Chemistry. 2024. Vol. 61. No. 10. P. 1554–1563.

Kudryavtseva E. N., Lichitsky B. V., Komogortsev A. N., Милютин К. В., Tretyakov E. V.

For the first time, the possibility of using hexafluoro-1,4-naphthoquinone for the construction of condensed heterocyclic system was demonstrated. As a result, two-step synthesis of previously unknown 5,6,7,8-tetrafluoro-1H-benzo[f]indol-4,9-dione derivatives was elaborated. The suggested method includes initial interaction of hexafluoro-1,4-naphthoquinone with various methyl 3-aminocrotonates and subsequent intramolecular cyclization into the target fluorinated benzo[f]indole-4,9-diones. The distinctive feature of considered protocol is regiospecific reaction of fluorine atoms in quinone fragment. Advantages of the presented approach are simple synthetic procedure avoiding chromatographic purification, atom economy and readily available starting materials. The structure of one of the synthesized compounds was established by x-ray analysis.

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

Kudryavtseva E. N., Lichitsky B. V., Komogortsev A. N. et al., Journal of Heterocyclic Chemistry 2024 Vol. 61 No. 12 P. 1932–1941

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 ...

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