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

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 Full article

Journal

Journal of Heterocyclic Chemistry
ISSN: 0022-152X , E-ISSN: 1943-5193

Output data

Year: 2024, Volume: 61, Number: 10, Pages: 1554-1563 Pages count : 10 DOI: 10.1002/jhet.4872

Authors

Kudryavtseva Ekaterina N. ¹ , Lichitsky Boris V. ¹ , Komogortsev Andrey N. ¹ , Milyutin Constantine V. ¹ , Tretyakov Evgeny V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Science Moscow Russian Federation

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.

Kudryavtseva E.N. , Lichitsky B.V. , Komogortsev A.N. , Milyutin C.V. , Tretyakov E.V.
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. V.61. N10. P.1554-1563. DOI: 10.1002/jhet.4872 Scopus OpenAlex

Scopus:	2-s2.0-85199284825
OpenAlex:	W4400924715

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